Enantioselective Organocatalytic Michael Addition of Isorhodanines. to α, β-unsaturated Aldehydes
|
|
- Ναχώρ Μιαούλης
- 6 χρόνια πριν
- Προβολές:
Transcript
1 Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2016 Enantioselective Organocatalytic Michael Addition of Isorhodanines to α, β-unsaturated Aldehydes Supporting Information Contents: 1. Preparation of substrates S2 2. X-ray structure of compound 3a S5 3. NMR Spectra S7 4. HPLC Profiles S43 S1
2 Preparation of substrates To a solution of thiazolidine-2,4-dione (0.61 g, 5.2 mmol, 1.0 equiv) in dry toluene (12.0 ml) was added Lawesson s reagent (2.2 g, 5.2 mmol, 1.0 equiv). The reaction mixture was refluxed for 2 h and cooled to room temperature. The solid was filtered off and crystallized from acetone to afford isorhodanine (0.64 g, 98% yield) as a yellow crystal. 1 H NMR (600 MHz, DMSO-d 6, TMS): δ = (s, 1H), 4.67 (s, 2H); MS (ESI) m/z: [M+H] +. To a solution of isorhodanine (0.60 g, 4.5 mmol, 1.0 equiv) in DMF (10.0 ml) was added NaH (0.19 g, 4.9 mmol, 1.1 equiv) and the mixture was stirred for 0.5 h at 0 C. Then, iodomethane (0.75 g, 4.5 mmol, 1.0 equiv) was added and the reaction mixture was stirred for 1 h. Water (30.0 ml) was added to the reaction mixture and extracted by ethyl acetate (15.0 ml 3). The organic layer was dried over Na 2 SO 4, and concentrated to give the crude product, which was further purified by column chromatography to yield the desired substrate 2a. The synthetic method for substrates 2b-k was similar to the synthesis of substrate 2a. For substrate 2l, 2 equivalent of iodomethane was used. 4-(Methylthio)thiazol-2(3H)-one (2a). 1 H NMR (600 MHz, DMSO-d 6, TMS): δ = (s, 1H), 6.26 (s, 1H), 2.41 (s, 3H); 13 C NMR (150 MHz, CDCl 3, TMS): δ = , , , 17.08; HRMS (ESI) calcd for C 4 H 6 NO 2 S 2 [M+H] + = , found (Ethylthio)thiazol-2(3H)-one (2b). 1 H NMR (600 MHz, DMSO-d 6, TMS): δ = (s, 1H), (m, 1H), 2.85 (dd, J = 7.0, 14.6 Hz, 2H), 1.19 (t, J = 7.5 Hz, 3H); 13 C NMR (150 MHz, DMSO-d 6, TMS): δ = , , , 27.64, 14.75; HRMS (ESI) calcd for C 5 H 8 NOS 2 [M+H] + = , found ((Naphthalen-2-ylmethyl)thio)thiazol-2(3H)-one (2c). 1 H NMR (600 MHz, CDCl 3, TMS): δ = 9.67 (s, 1H), (m, 2H), (m, 1H), 7.62 (s, 1H), (m, 2H), 7.40 (dd, J = 1.8, 8.4 Hz, 1H), 6.03 (s, 1H), 4.13 (s, 2H); 13 C NMR (150 MHz, DMSO-d 6, TMS) δ = , , , , S2
3 127.25, , , , 39.72, 29.20; HRMS (ESI) calcd for C 14 H 12 NOS 2 [M+H] + = , found ((3-Fluorobenzyl)thio)thiazol-2(3H)-one (2d). 1 H NMR (600 MHz,CDCl 3, TMS): δ = (s, 1H), (m, 1H), (m, 3H), 6.08 (s, 1H), 3.97 (s, 2H); 13 C NMR (150 MHz, CDCl 3, TMS): δ = , , , , , , , 24.56, , , , , , , , 39.11, 39.08; HRMS (ESI) calcd for C 10 H 7 FNOS 2 [M-H] - = , found ((2-Methylbenzyl)thio)thiazol-2(3H)-one (2e). 1 H NMR (600 MHz, DMSO-d 6, TMS): δ = (s, 1H), (m, 2H), (m, 2H), 6.29 (d, J = 1.7 Hz, 1H), 4.09 (s, 2H), 2.32 (s, 3H); 13 C NMR (150 MHz, DMSO-d 6, TMS): δ = , , , , , , , , , 36.44, 19.14; HRMS (ESI) calcd for C 11 H 12 NOS 2 [M+H] + = , found ((4-Methylbenzyl)thio)thiazol-2(3H)-one (2f). 1 H NMR (300 MHz, DMSO-d 6, TMS): δ = (s, 1H), 7.11 (s, 4H), 6.27 (d, J = 1.8 Hz, 1H), 4.05 (s, 2H), 2.26 (s, 3H); 13 C NMR (75 MHz, DMSO-d 6, TMS): δ = , , , , , , , 37.54, 21.18; HRMS (ESI) calcd for C 11 H 12 NOS 2 [M+H] + = , found ((2-Nitrobenzyl)thio)thiazol-2(3H)-one (2g). 1 H NMR (500 MHz, DMSO-d 6, TMS): δ = (s, 1H), 8.04 (dd, J = 1.1, 8.1 Hz, 1H), 7.68 (td, J = 1.2, 7.5, 15.2 Hz, 1H), 7.55 (td, J = 1.3, 8.2, 15.5 Hz, 1H), 7.38 (dd, J = 1.2, 7.7 Hz, 1H), 6.27 (d, J = 1.6 Hz, 1H), 4.35 (s, 2H), 13 C NMR (125 MHz, DMSO-d 6, TMS) δ = , , , , , , , , , 35.53; HRMS (ESI) calcd for C 10 H 7 N 2 O 3 S 2 [M-H] - = , found ((4-Nitrobenzyl)thio)thiazol-2(3H)-one (2h). 1 H NMR (500 MHz, DMSO-d 6, TMS): δ = (s, 1H), 8.19 (d, J = 9.1 Hz, 2H), 7.49 (d, J = 9.1 Hz, 2H), 6.30 (d, J = 0.9 Hz, 1H), 4.22 (s, 2H); 13 C NMR (125 MHz, DMSO-d 6, S3
4 TMS): δ = , , , , , , , 37.05; HRMS (ESI) calcd for C 10 H 7 N 2 O 3 S 2 [M-H] - = , found (((2-Oxo-2,3-dihydrothiazol-4-yl)thio)methyl)benzonitrile (2i). 1 H NMR (300 MHz, DMSO-d 6, TMS): δ = (s, 1H), 7.81 (d, J = 8.1 Hz, 2H), 7.42 (d, J = 8.2 Hz, 2H), 6.32 (d, J = 1.3 Hz, 1H), 4.18 (s, 2H); 13 C NMR (75 MHz, DMSO-d 6, TMS): δ = , , , , , , , 37.32; HRMS (ESI) calcd for C 11 H 9 N 2 OS 2 [M+H] - = , found ((4-(Tert-butyl)benzyl)thio)thiazol-2(3H)-one (2j). 1 H NMR (300 MHz, DMSO-d 6, TMS): δ = (s, 1H), 7.33 (d, J = 8.3 Hz, 2H), 7.17 (d, J = 8.3 Hz, 2H), 6.31 (d, J = 1.6 Hz, 1H), 4.10 (s, 2H), 1.24 (s, 9H); 13 C NMR (75 MHz, DMSO-d 6, TMS): δ = , , , , , , , 37.38, 34.69, 31.56; HRMS (ESI) calcd for C 14 H 18 NOS 2 [M+H] + = , found ((2-Oxo-2,3-dihydrothiazol-4-yl)thio)acetonitrile (2k). 1 H NMR (600 MHz, DMSO-d 6, TMS): δ = (s, 1H), 6.80 (s, 1H), 4.06 (s, 1H); 13 C NMR (150 MHz, DMSO-d 6, TMS): δ = 175.5, , , , 41.33; HRMS (ESI) calcd for C 5 H 3 N 2 OS 2 [M-H] - = , found Methyl-4-(methylthio)thiazol-2(3H)-one (2l). 1 H NMR (600 MHz, CDCl 3, TMS): δ = 7.27 (s, 1H), 6.04 (s, 1H), 3.33 (s,3h), 2.36 (s, 3H); HRMS (ESI) calcd for C 5 H 8 NOS 2 [M+H] + = , found S4
5 X-ray structure of 3a Table 1. Crystal data and structure refinement for 3a. Identification code Empirical formula mo_21229a C19H19NO2S2 Formula weight Temperature Wavelength Crystal system, space group 296(2) K Å Orthorhombic, P2(1)2(1)2(1) Unit cell dimensions a = (13) Å alpha = 90 deg. b = (15) Å c = (18) Å Volume (4) Å 3 Z, Calculated density 4, Mg/m 3 Absorption coefficient mm -1 beta = 90 deg. gamma = 90 deg. F(000) 752 Crystal size Theta range for data collection Limiting indices 0.12 x 0.11 x 0.09 mm 2.24 to deg. -14<=h<=14, -14<=k<=14, -19<=l<=16 Reflections collected / unique / 4244 [R(int) = ] Completeness to theta = % Absorption correction Semi-empirical from equivalents Max. and min. transmission and Refinement method Full-matrix least-squares on F 2 Data / restraints / parameters 4244 / 1 / 225 S5
6 Goodness-of-fit on F Final R indices [I>2sigma(I)] R1 = , wr2 = R indices (all data) R1 = , wr2 = Absolute structure parameter 0.00(12) Largest diff. peak and hole and e. Å -3 S6
7 NMR Spectra Compound 3a S7
8 Compound 3b S8
9 Compound 3c S9
10 Compound 3d S10
11 Compound 3e S11
12 Compound 3f S12
13 Compound 3g S13
14 Compound 3h S14
15 Compound 3i S15
16 Compound 3j S16
17 Compound 3k S17
18 Compound 3l S18
19 Compound 3m S19
20 Compound 4a S20
21 Compound 4b S21
22 Compound 4c S22
23 Compound 4d S23
24 Compound 4e S24
25 Compound 4f S25
26 Compound 4g S26
27 Compound 4h S27
28 Compound 4i S28
29 Compound 4j S29
30 Compound 4k S30
31 Compound 2a S31
32 Compound 2b S32
33 Compound 2c S33
34 Compound 2d S34
35 Compound 2e S35
36 Compound 2f S36
37 Compound 2g S37
38 Compound 2h S38
39 Compound 2i S39
40 Compound 2j S40
41 Compound 2k S41
42 Compound 2l S42
43 HPLC Chromatograms Compound 3a S43
44 Compound 3b S44
45 Compound 3c S45
46 Compound 3d S46
47 Compound 3e S47
48 Compound 3f S48
49 Compound 3g S49
50 Compound 3h S50
51 Compound 3i S51
52 Compound 3j S52
53 Compound 3k S53
54 Compound 3l S54
55 Compound 3m S55
56 Compound 4a S56
57 Compound 4b S57
58 Compound 4c S58
59 Compound 4d S59
60 Compound 4e S60
61 Compound 4f S61
62 Compound 4g S62
63 Compound 4h S63
64 Compound 4i S64
65 Compound 4j S65
66 Compound 4k S66
Cycloaddition of Homochiral Dihydroimidazoles: A 1,3-Dipolar Cycloaddition Route to Optically Active Pyrrolo[1,2-a]imidazoles
X-Ray crystallographic data tables for paper: Supplementary Material (ESI) for Organic & Biomolecular Chemistry Cycloaddition of Homochiral Dihydroimidazoles: A 1,3-Dipolar Cycloaddition Route to Optically
Διαβάστε περισσότεραSupporting Information for. Catalytic C H α-trifluoromethylation of α,β-unsaturated Carbonyl Compounds
Supporting Information for Catalytic C H α-trifluoromethylation of α,β-unsaturated Carbonyl Compounds Zhongxue Fang, a Yongquan Ning, a Pengbing Mi, a Peiqiu Liao, a Xihe Bi* a,b a Department of Chemistry,
Διαβάστε περισσότεραSUPPLEMENTARY MATERIAL. A Facile and Convenient Approach for the Synthesis of Novel Sesamol-Oxazine and Quinoline- Oxazine Hybrids
10.1071/CH17272_AC CSIRO 2017 Australian Journal of Chemistry 2017, 70(12), 1285-1290 SUPPLEMENTARY MATERIAL A Facile and Convenient Approach for the Synthesis of Novel Sesamol-Oxazine and Quinoline- Oxazine
Διαβάστε περισσότεραchlorostibine Iou-Sheng Ke and François P. Gabbai Department of Chemistry, Texas A&M University, College Station, TX
σ-donor/acceptor confused ligands: The case of a chlorostibine Iou-Sheng Ke and François P. Gabbai Department of Chemistry, Texas A&M University, College Station, TX 77843-3255. *To whom correspondence
Διαβάστε περισσότεραElectronic Supplementary Information (ESI)
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2016 Electronic Supplementary Information (ESI) Cyclopentadienyl iron dicarbonyl (CpFe(CO) 2 ) derivatives
Διαβάστε περισσότεραEnantioselective Synthesis of the Anti-inflammatory Agent ( )-Acanthoic Acid
Enantioselective Synthesis of the Anti-inflammatory Agent ( )-Acanthoic Acid Taotao Ling, a Chinmay Chowdhury, a Bryan A. Kramer, a Binh G. Vong, a Michael A. Palladino b and Emmanuel A. Theodorakis a
Διαβάστε περισσότεραSupporting Information
Supporting Information Transition-metal-free Ring Expansion Reactions of Indene-1,3-dione: Synthesis of Functionalized Benzoannulated Seven-Membered Ring Compounds Qiyi Yao, Lingkai Kong, Mengdan Wang,
Διαβάστε περισσότεραPhoto-Induced Self-Assembly of Pt(II)-Linked Rings and Cages via the Photolabilization of a Pt(II) Pyridine Bond
Photo-Induced Self-Assembly of Pt(II)-Linked Rings and Cages via the Photolabilization of a Pt(II) Pyridine Bond Ken-ichi Yamashita, Kei-ichi Sato, Masaki Kawano and Makoto Fujita* Contents; Figure S1.
Διαβάστε περισσότεραCopper-catalyzed formal O-H insertion reaction of α-diazo-1,3-dicarb- onyl compounds to carboxylic acids with the assistance of isocyanide
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2014 Copper-catalyzed formal O-H insertion reaction of α-diazo-1,3-dicarb- onyl compounds to carboxylic
Διαβάστε περισσότεραSupporting Information for: Intramolecular Hydrogen Bonding-Assisted Cyclocondensation of. 1,2,3-Triazole Synthesis
Supporting Information for: Intramolecular Hydrogen Bonding-Assisted Cyclocondensation of α-diazoketones with Various Amines: A Strategy for Catalytic Wolff 1,2,3-Triazole Synthesis Zikun Wang, a Xihe
Διαβάστε περισσότεραNickel and Platinum PCP Pincer Complexes Incorporating an Acyclic Diaminoalkyl Central Moiety Connecting Imidazole or Pyrazole Rings
ickel and Platinum PCP Pincer Complexes Incorporating an Acyclic Diaminoalkyl Central Moiety Connecting Imidazole or Pyrazole Rings Braulio M. Puerta Lombardi, Rudy M. Braun, Chris Gendy, Chia Yun Chang,
Διαβάστε περισσότεραPatrycja Miszczyk, Dorota Wieczorek, Joanna Gałęzowska, Błażej Dziuk, Joanna Wietrzyk and Ewa Chmielewska. 1. Spectroscopic Data.
; doi:10.3390/molecules22020254 S1 of S23 Supplementary Materials: Reaction of 3-Amino-1,2,4-Triazole with Diethyl Phosphite and Triethyl Orthoformate: Acid-Base Properties and Antiosteoporotic Activities
Διαβάστε περισσότεραSupporting Information
Supporting Information Vinylogous elimination/heck coupling/allylation domino reactions: access to 2- substituted 2,3-dihydrobenzofurans and indolines Jianguo Yang, *, Hanjie Mo, Xiuxiu Jin, Dongdong Cao,
Διαβάστε περισσότεραIV. ANHANG 179. Anhang 178
Anhang 178 IV. ANHANG 179 1. Röntgenstrukturanalysen (Tabellen) 179 1.1. Diastereomer A (Diplomarbeit) 179 1.2. Diastereomer B (Diplomarbeit) 186 1.3. Aldoladdukt 5A 193 1.4. Aldoladdukt 13A 200 1.5. Aldoladdukt
Διαβάστε περισσότεραSupporting Information. Research Center for Marine Drugs, Department of Pharmacy, State Key Laboratory
Supporting Information Dysiherbols A C and Dysideanone E, Cytotoxic and NF-κB Inhibitory Tetracyclic Meroterpenes from a Dysidea sp. Marine Sponge Wei-Hua Jiao,, Guo-Hua Shi,, Ting-Ting Xu,, Guo-Dong Chen,
Διαβάστε περισσότεραSupporting Information
Supporting Information Gold-catalyzed Cycloisomerization of 1,6-Diyne-4-en-3-ols to form Naphthyl Ketone Derivatives. Jian-Jou Lian and Rai-Shung Liu* Department of Chemistry, National Tsing-Hua University,
Διαβάστε περισσότεραSupporting Information for
Supporting Information for An atom-economic route to densely functionalized thiophenes via base-catalyzed rearrangement of 5-propargyl-2H-thiopyran-4(3H)-ones Chunlin Tang a, Jian Qin b, Xingqi Li *a a
Διαβάστε περισσότεραDivergent synthesis of various iminocyclitols from D-ribose
Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 205 Divergent synthesis of various iminocyclitols from D-ribose Ramu Petakamsetty,
Διαβάστε περισσότεραA facile and general route to 3-((trifluoromethyl)thio)benzofurans and 3-((trifluoromethyl)thio)benzothiophenes
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2014 A facile and general route to 3-((trifluoromethyl)thio)benzofurans and 3-((trifluoromethyl)thio)benzothiophenes
Διαβάστε περισσότεραSupplementary Figure S1. Single X-ray structure 3a at probability ellipsoids of 20%.
Supplementary Figure S1. Single X-ray structure 3a at probability ellipsoids of 20%. S1 Supplementary Figure S2. Single X-ray structure 5a at probability ellipsoids of 20%. S2 H 15 Ph Ac Ac I AcH Ph Ac
Διαβάστε περισσότεραSupporting Information. A catalyst-free multicomponent domino sequence for the. diastereoselective synthesis of (E)-3-[2-arylcarbonyl-3-
Supporting Information for A catalyst-free multicomponent domino sequence for the diastereoselective synthesis of (E)-3-[2-arylcarbonyl-3- (arylamino)allyl]chromen-4-ones Pitchaimani Prasanna 1, Pethaiah
Διαβάστε περισσότεραSupporting Information
Supporting Information for AgOTf-catalyzed one-pot reactions of 2-alkynylbenzaldoximes with α,β-unsaturated carbonyl compounds Qiuping Ding 1, Dan Wang 1, Puying Luo* 2, Meiling Liu 1, Shouzhi Pu* 3 and
Διαβάστε περισσότεραSupporting Information. for
Supporting Information for A general synthetic route to [Cu(X)(NHC)] (NHC = N- heterocyclic carbene, X =Cl, Br, I) complexes Orlando Santoro, Alba Collado, Alexandra M. Z. Slawin, Steven P. Nolan and Catherine
Διαβάστε περισσότεραElectronic supplementary information (ESI) Bodipy functionalized ortho-carborane dyads for low-energy photosensitization
Electronic Supplementary Material (ESI) for Dalton Transactions. This journal is The Royal Society of Chemistry 2014 Electronic supplementary information (ESI) Bodipy functionalized ortho-carborane dyads
Διαβάστε περισσότεραPractical Pd(II)-catalyzed C H Alkylation with Epoxides: One-step Syntheses of 3,4-Dihydroisocoumarins
Practical Pd(II)-catalyzed C H Alkylation with Epoxides: One-step Syntheses of 3,4-Dihydroisocoumarins Guolin Cheng, Tuan-Jie Li, and Jin-Quan Yu* Department of Chemistry, The Scripps Research Institute,
Διαβάστε περισσότεραSupporting Information
Supporting Information for Lewis acid-catalyzed redox-neutral amination of 2-(3-pyrroline-1-yl)benzaldehydes via intramolecular [1,5]-hydride shift/isomerization reaction Chun-Huan Jiang, Xiantao Lei,
Διαβάστε περισσότεραCopper-Catalyzed Oxidative Dehydrogenative N-N Bond. Formation for the Synthesis of N,N -Diarylindazol-3-ones
Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers. This journal is the Partner Organisations 2016 Supporting information Copper-Catalyzed Oxidative Dehydrogenative - Bond Formation
Διαβάστε περισσότεραSynthesis of novel 1,2,3-triazolyl derivatives of pregnane, androstane and D-homoandrostane. Tandem Click reaction/cu-catalyzed D-homo rearrangement
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2014 Supporting Information Synthesis of novel 1,2,3-triazolyl derivatives of
Διαβάστε περισσότεραMetal-free Oxidative Coupling of Amines with Sodium Sulfinates: A Mild Access to Sulfonamides
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2014 Supporting information for Metal-free Oxidative Coupling of Amines with Sodium Sulfinates:
Διαβάστε περισσότεραElectronic Supplementary Information
Electronic Supplementary Information Unprecedented Carbon-Carbon Bond Cleavage in Nucleophilic Aziridine Ring Opening Reaction, Efficient Ring Transformation of Aziridines to Imidazolidin-4-ones Jin-Yuan
Διαβάστε περισσότεραPalladium-Catalyzed Direct ortho-sulfonylation of. Azobenzenes with Arylsulfonyl Chlorides via C H. Table of Contents
Electronic upplementary Material (EI) for RC Advances. This journal is The Royal ociety of Chemistry 205 upporting Information Palladium-Catalyzed Direct ortho-ulfonylation of Azobenzenes with Arylsulfonyl
Διαβάστε περισσότεραSupplementary Information. Living Ring-Opening Polymerization of Lactones by N-Heterocyclic Olefin/Al(C 6 F 5 ) 3
Supplementary Information Living Ring-Opening Polymerization of Lactones by N-Heterocyclic Olefin/Al(C 6 F 5 ) 3 Lewis Pairs: Structures of Intermediates, Kinetics, and Mechanism Qianyi Wang, Wuchao Zhao,
Διαβάστε περισσότεραSupporting Information
Supporting Information Montmorillonite KSF-Catalyzed One-pot, Three-component, Aza-Diels- Alder Reactions of Methylenecyclopropanes With Arylaldehydes and Aromatic Amines Li-Xiong Shao and Min Shi* General
Διαβάστε περισσότερα9-amino-(9-deoxy)cinchona alkaloids-derived novel chiral phase-transfer catalysts
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2014 9-amino-(9-deoxy)cinchona alkaloids-derived novel chiral phase-transfer
Διαβάστε περισσότεραSupporting Information
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2018 Supporting Information Silver or Cerium-Promoted Free Radical Cascade Difunctionalization
Διαβάστε περισσότεραRoom Temperature Highly Diastereoselective Zn-Mediated. Allylation of Chiral N-tert-Butanesulfinyl Imines: Remarkable Reaction Condition Controlled
Supporting Information for: Room Temperature Highly Diastereoselective Zn-Mediated Allylation of Chiral N-tert-Butanesulfinyl Imines: Remarkable Reaction Condition Controlled Stereoselectivity Reversal
Διαβάστε περισσότεραSynthesis and evaluation of novel aza-caged Garcinia xanthones
Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry Synthesis and evaluation of novel aza-caged Garcinia xanthones Xiaojin Zhang, a,1 Xiang Li, a,1 Haopeng Sun, * b Zhengyu Jiang,
Διαβάστε περισσότεραSupporting Information. Copyright Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2006
Supporting Information Copyright Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2006 1 A Facile Way to Synthesize 2H-Chromenes: Reconsideration of the Reaction Mechanism between Salicylic Aldehyde and
Διαβάστε περισσότεραDirect Transformation of Ethylarenes into Primary Aromatic Amides with N-Bromosuccinimide and I 2 -aq NH 3
Supporting Information Direct Transformation of Ethylarenes into Primary Aromatic Amides with N-Bromosuccinimide and I 2 -aq NH 3 Shohei Shimokawa, Yuhsuke Kawagoe, Katsuhiko Moriyama, Hideo Togo* Graduate
Διαβάστε περισσότεραSupporting Information
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2015 Synthesis of 3-omosubstituted Pyrroles via Palladium- Catalyzed Intermolecular Oxidative Cyclization
Διαβάστε περισσότεραSupporting Information One-Pot Approach to Chiral Chromenes via Enantioselective Organocatalytic Domino Oxa-Michael-Aldol Reaction
Supporting Information ne-pot Approach to Chiral Chromenes via Enantioselective rganocatalytic Domino xa-michael-aldol Reaction Hao Li, Jian Wang, Timiyin E-Nunu, Liansuo Zu, Wei Jiang, Shaohua Wei, *
Διαβάστε περισσότεραCobalt-Catalyzed Selective Synthesis of Isoquinolines Using Picolinamide as a Traceless Directing Group
Supporting Information Cobalt-Catalyzed Selective Synthesis of Isoquinolines Using Picolinamide as a Traceless Directing Group Changsheng Kuai, Lianhui Wang, Bobin Li, Zhenhui Yang, Xiuling Cui* Engineering
Διαβάστε περισσότεραSupporting Information
Electronic Supplementary Material (ESI) for Dalton Transactions. This journal is The Royal Society of Chemistry 2016 Supporting Information Abnormal N-Heterocyclic Carbene Based Nickel Complex for Catalytic
Διαβάστε περισσότεραSupporting Information for
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2015 Supporting Information for Catalytic Asymmetric Chemoselective 1,3-Dipolar Cycloadditions of Azomethine
Διαβάστε περισσότεραSupporting information for
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2014 Supporting information for Palladium-Catalyzed Benzothieno[2,3-b]indole Formation via Dehydrative-Dehydrogenative
Διαβάστε περισσότεραDirect Palladium-Catalyzed Arylations of Aryl Bromides. with 2/9-Substituted Pyrimido[5,4-b]indolizines
Direct Palladium-Catalyzed Arylations of Aryl Bromides with 2/9-Substituted Pyrimido[5,4-b]indolizines Min Jiang, Ting Li, Linghua Meng, Chunhao Yang,* Yuyuan Xie*, and Jian Ding State Key Laboratory of
Διαβάστε περισσότεραMultifunctinality and Crystal Dynamics of Highly Stable Porous Metal-Organic Framework [Zn 4 O(NTB) 2 ]
Supporting Information Multifunctinality and Crystal Dynamics of Highly Stable Porous Metal-Organic Framework [Zn 4 O(NTB) 2 ] Eun Young Lee, Seung Yeon Jang, and Myunghyun Paik Suh* School of Chemistry,
Διαβάστε περισσότεραFirst DMAP-mediated direct conversion of Morita Baylis. Hillman alcohols into γ-ketoallylphosphonates: Synthesis of
Supporting Information File 1 for First DMAP-mediated direct conversion of Morita Baylis Hillman alcohols into γ-ketoallylphosphonates: Synthesis of γ-aminoallylphosphonates Marwa Ayadi 1,2, Haitham Elleuch
Διαβάστε περισσότεραSupporting Information File 2. Crystallographic data of syn-bis-quinoxaline, 16c CH 3 CO 2 C 2 H 5 ;
Supporting Information File 2 Crystallographic data of syn-bis-quinoxaline, 16c CH 3 CO 2 C 2 H 5 ; Preparation, structures and host guest chemistry of fluorinated syn-bisquinoxaline molecular tweezers
Διαβάστε περισσότεραSupporting Information
Supporting Information Copper/Silver Cocatalyzed Oxidative Coupling of Vinylarenes with ICH 2 CF 3 or ICH 2 CHF 2 Leading to β-cf 3 /CHF 2 -Substituted Ketones Niannian Yi, Hao Zhang, Chonghui Xu, Wei
Διαβάστε περισσότεραSupporting information
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2014 Supporting information Copper-catalysed intramolecular O-arylation: a simple
Διαβάστε περισσότεραSupporting Information
Supporting Information Ceric Ammonium Nitrate (CAN) catalyzed efficient one-pot three component aza-diels-alder reactions for a facile synthesis of tetrahydropyranoquinoline derivatives Ravinder Goud Puligoundla
Διαβάστε περισσότεραSite-Selective Suzuki-Miyaura Cross-Coupling Reactions of 2,3,4,5-Tetrabromofuran
1 Site-Selective Suzuki-Miyaura Cross-Coupling Reactions of 2,3,4,5-Tetrabromofuran Munawar Hussain, a Rasheed Ahmad Khera, a Nguyen Thai Hung, a Peter Langer* a,b a Institut für Chemie, Universität Rostock,
Διαβάστε περισσότεραSupporting Information. Microwave-assisted construction of triazole-linked amino acid - glucoside conjugates as novel PTP1B inhibitors
Supporting Information Microwave-assisted construction of triazole-linked amino acid - glucoside conjugates as novel PTP1B inhibitors Xiao-Peng He, abd Cui Li, d Xiao-Ping Jin, b Zhuo Song, b Hai-Lin Zhang,
Διαβάστε περισσότεραand Selective Allylic Reduction of Allylic Alcohols and Their Derivatives with Benzyl Alcohol
FeCl 3 6H 2 O-Catalyzed Disproportionation of Allylic Alcohols and Selective Allylic Reduction of Allylic Alcohols and Their Derivatives with Benzyl Alcohol Jialiang Wang, Wen Huang, Zhengxing Zhang, Xu
Διαβάστε περισσότεραFluorinative Ring-opening of Cyclopropanes by Hypervalent Iodine Reagents. An Efficient Method for 1,3- Oxyfluorination and 1,3-Difluorination
Electronic Supplementary Material (ESI) for Chemical Science. This journal is The Royal Society of Chemistry 2016 Supporting Information Fluorinative Ring-opening of Cyclopropanes by Hypervalent Iodine
Διαβάστε περισσότεραElectronic Supplementary Information
Electronic Supplementary Material (ESI) for Polymer hemistry This journal is The Royal Society of hemistry 2011 Phosphoric and Phosphoramidic Acids as Bifunctional atalysts for the Ring-pening Polymerization
Διαβάστε περισσότεραSupporting Information for Substituent Effects on the Properties of Borafluorenes
Supporting Information for Substituent Effects on the Properties of Borafluorenes Mallory F. Smith, S. Joel Cassidy, Ian A. Adams, Monica Vasiliu, Deidra L. Gerlach, David Dixon*, Paul A. Rupar* Department
Διαβάστε περισσότεραSupplementary information
Electronic Supplementary Material (ESI) for MedChemComm. This journal is The Royal Society of Chemistry 2015 Supplementary information Synthesis of carboxyimidamide-substituted benzo[c][1,2,5]oxadiazoles
Διαβάστε περισσότεραRegioselectivity in the Stille coupling reactions of 3,5- dibromo-2-pyrone.
Regioselectivity in the Stille coupling reactions of 3,5- dibromo-2-pyrone. Won-Suk Kim, Hyung-Jin Kim and Cheon-Gyu Cho Department of Chemistry, Hanyang University, Seoul 133-791, Korea Experimental Section
Διαβάστε περισσότεραHighly enantioselective cascade synthesis of spiropyrazolones. Supporting Information. NMR spectra and HPLC traces
Highly enantioselective cascade synthesis of spiropyrazolones Alex Zea a, Andrea-Nekane R. Alba a, Andrea Mazzanti b, Albert Moyano a and Ramon Rios a,c * Supporting Information NMR spectra and HPLC traces
Διαβάστε περισσότεραSupplementary Data. Engineering, Nanjing University, Nanjing , P. R. China;
Supplementary Data Synthesis, Chemo-selective Properties of Substituted 9-Aryl-9H-fluorenes from Triarylcarbinols and Enantiomerical Kinetics of Chiral 9-Methoxy-11-(naphthalen-1-yl)-11H-benzo[a]fluorene
Διαβάστε περισσότεραSupporting Information
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2017 Supporting Information Domino reaction of cyclic sulfamidate imines with
Διαβάστε περισσότεραSupporting Information. Experimental section
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2014 Supporting Information Experimental section General. Proton nuclear magnetic resonance ( 1
Διαβάστε περισσότεραSupporting Information. Experimental section
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2014 Supporting Information Experimental section General. Anhydrous solvents were transferred by
Διαβάστε περισσότεραSupporting information
Electronic Supplementary Material (ESI) for Green Chemistry. This journal is The Royal Society of Chemistry 204 Supporting information Palladium nanoparticles supported on triazine functionalised mesoporous
Διαβάστε περισσότεραFused Bis-Benzothiadiazoles as Electron Acceptors
Fused Bis-Benzothiadiazoles as Electron Acceptors Debin Xia, a,b Xiao-Ye Wang, b Xin Guo, c Martin Baumgarten,*,b Mengmeng Li, b and Klaus Müllen*,b a MIIT Key Laboratory of ritical Materials Technology
Διαβάστε περισσότεραConstruction of Cyclic Sulfamidates Bearing Two gem-diaryl Stereocenters through a Rhodium-Catalyzed Stepwise Asymmetric Arylation Protocol
Supporting Information for: Construction of Cyclic Sulfamidates Bearing Two gem-diaryl Stereocenters through a Rhodium-Catalyzed Stepwise Asymmetric Arylation Protocol Yu-Fang Zhang, Diao Chen, Wen-Wen
Διαβάστε περισσότεραSupporting Information. Asymmetric Binary-acid Catalysis with Chiral. Phosphoric Acid and MgF 2 : Catalytic
Supporting Information Asymmetric Binary-acid Catalysis with Chiral Phosphoric Acid and MgF 2 : Catalytic Enantioselective Friedel-Crafts Reactions of β,γ- Unsaturated-α-Ketoesters Jian Lv, Xin Li, Long
Διαβάστε περισσότεραL. Kaßner a, K. Nagel a, R. E. Grützner b, M. Korb c, T. Rüffer c, H. Lang c and S. Spange a
Electronic Supplementary Material (ESI) for Polymer Chemistry. This journal is The Royal Society of Chemistry 2015 Supplementary Information L. Kaßner a, K. Nagel a, R. E. Grützner b, M. Korb c, T. Rüffer
Διαβάστε περισσότεραKishore Natte, Jianbin Chen, Helfried Neumann, Matthias Beller, and Xiao-Feng Wu*
Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 204 Kishore Natte, Jianbin Chen, Helfried Neumann, Matthias Beller, and Xiao-Feng
Διαβάστε περισσότεραSupporting Information
Supporting Information Selective Synthesis of xygen-containing Heterocycles via Tandem Reactions of 1,2-Allenic Ketones with Ethyl 4-Chloroacetoacetate Qiang Wang, a, b Zhouqing Xu b and Xuesen Fan a *
Διαβάστε περισσότεραSupporting Information. Copyright Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2007
Supporting Information Copyright Wiley-VCH Verlag GmbH & Co. KGaA, 6945 Weinheim, 2007 A New Method for Constructing Quaternary Carbon Centres: Tandem Rhodium-Catalysed,4-Addition/Intramolecular Cyclization.
Διαβάστε περισσότεραSupporting Information for
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2015 Supporting Information for Quinine-Catalyzed Highly Enantioselective Cycloannulation
Διαβάστε περισσότεραSelective mono reduction of bisphosphine
Griffith Research Online https://research-repository.griffith.edu.au Selective mono reduction of bisphosphine oxides under mild conditions Author etersson, Maria, Loughlin, Wendy, Jenkins, Ian ublished
Διαβάστε περισσότεραElectronic Supplementary Information (ESI)
Electronic Supplementary Material (ESI) for Dalton Transactions. This journal is The Royal Society of Chemistry 2016 Electronic Supplementary Information (ESI) CPh 3 as a functional group in P-heterocyclic
Διαβάστε περισσότεραSupporting Information
Supporting Information Novel ne-pot Synthesis of Polysubstituted Isocoumarins from Arynes and Trifluoroacetylated β-diketones Kentaro kuma,* Koki Hirano, Yukiko Tanabe, Ryoichi Itoyama, Atsumi Miura, Noriyoshi
Διαβάστε περισσότεραChiral Brønsted Acid Catalyzed Enantioselective Intermolecular Allylic Aminations. Minyang Zhuang and Haifeng Du*
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2014 Chiral Brønsted Acid Catalyzed Enantioselective Intermolecular Allylic
Διαβάστε περισσότεραSupporting Information
Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2018 Supporting Information Direct C4-H osphonation of 8-Hydroxyquinoline Derivatives
Διαβάστε περισσότεραTable of Contents 1 Supplementary Data MCD
Electronic Supplementary Material (ESI) for Dalton Transactions. This journal is The Royal Society of Chemistry 2017 Supporting Information for Magnetic circular dichroism and density functional theory
Διαβάστε περισσότεραSupporting information. An unusual bifunctional Tb-MOF for highly sensing of Ba 2+ ions and remarkable selectivities of CO 2 /N 2 and CO 2 /CH 4
Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A. This journal is The Royal Society of Chemistry 2015 Supporting information An unusual bifunctional Tb-MOF for highly sensing
Διαβάστε περισσότεραSupporting Information. Palladium Complexes with Bulky Diphosphine. Synthesis of (Bio-) Adipic Acid from Pentenoic. Acid Mixtures.
Supporting Information Palladium Complexes with Bulky Diphosphine Ligands as Highly Selective Catalysts for the Synthesis of (Bio-) Adipic Acid from Pentenoic Acid Mixtures. Choon Heng Low, James D. Nobbs,*
Διαβάστε περισσότεραSupplementary Figure 1. (X-ray structures of 6p and 7f) O N. Br 6p
Supplementary Figure 1 (X-ray structures of 6p and 7f) Me Br 6p 6p Supplementary Figures 2-68 (MR Spectra) Supplementary Figure 2. 1 H MR of the 6a Supplementary Figure 3. 13 C MR of the 6a Supplementary
Διαβάστε περισσότεραIodine-catalyzed synthesis of sulfur-bridged enaminones and chromones via double C(sp 2 )-H thiolation
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2017 Iodine-catalyzed synthesis of sulfur-bridged enaminones and chromones via
Διαβάστε περισσότεραAg-Initiated gem-difluoromethylenation of the Nitrogen Center of. Arenediazonium Salts to gem-difluoromethylene Azo Compounds
Org. Lett. Supporting Information Ag-Initiated gem-difluoromethylenation of the Nitrogen Center of Arenediazonium Salts to gem-difluoromethylene Azo Compounds Haizhen Jiang,*,, Yunrong Chen, Bo Chen, Hui
Διαβάστε περισσότεραSUPPORTING INFORMATION. Pyramidanes: The Covalent Form of the Ionic Compounds
SUPPORTING INFORMATION Pyramidanes: The Covalent Form of the Ionic Compounds Vladimir Ya. Lee, 1 * Olga A. Gapurenko, 2 Yuki Ito, 1 Takahiko Meguro, 1 Haruka Sugasawa, 1 Akira Sekiguchi, 1 *, Ruslan M.
Διαβάστε περισσότεραSupporting Information for: Nickel-Catalyzed [4+2] Cycloaddition of Enones with Alkynes. Ichiro Koyama, Takuya Kurahashi,* and Seijiro Matsubara*
Supporting Information for: Nickel-Catalyzed [4+2] Cycloaddition of Enones with Alkynes Ichiro Koyama, Takuya Kurahashi,* and Seijiro Matsubara* Department of Material Chemistry, Graduate School of Engineering,
Διαβάστε περισσότεραTrisubstituted Alkenes Having Single Activator as Dipolarophile in. Highly Diastereo- and Enantioselective [3+2]-Cycloaddition with
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 218 Supporting Information Trisubstituted Alkenes Having Single Activator as Dipolarophile in Highly
Διαβάστε περισσότεραSupporting Information
Supporting Information Lewis acid catalyzed ring-opening reactions of methylenecyclopropanes with diphenylphosphine oxide in the presence of sulfur or selenium Min Shi,* Min Jiang and Le-Ping Liu State
Διαβάστε περισσότεραOxyhalogenation of thiols and disulfides into sulfonyl chlorides/ bromides in water using oxone-kx(x= Cl or Br)
Electronic Supplementary Material (ESI) for Green Chemistry. This journal is The Royal Society of Chemistry 2014 Oxyhalogenation of thiols and disulfides into sulfonyl chlorides/ bromides in water using
Διαβάστε περισσότεραThe N,S-Bidentate Ligand Assisted Pd-Catalyzed C(sp 2 )-H. Carbonylation using Langlois Reagent as CO Source. Supporting Information.
Electronic upplementary Material (EI) for rganic & Biomolecular Chemistry. This journal is The Royal ociety of Chemistry 2018 The,-Bidentate Ligand Assisted Pd-Catalyzed C(sp 2 )-H Carbonylation using
Διαβάστε περισσότεραSynthesis of spiropyrazoline oxindoles by a formal [4+1] annulation reaction between 3-bromooxindoles and in situ-derived 1,2-diaza-1,3- dienes
Electronic Supplementary Material (ESI) for rganic Chemistry Frontiers. This journal is the Partner rganisations 2017 Supporting Information for Synthesis of spiropyrazoline oxindoles by a formal [4+1]
Διαβάστε περισσότεραSUPPLEMENTARY MATERIAL
10.1071/CH16014_AC The Authors 2016 Australian Journal of Chemistry 2016, 69(9), 1049-1053 SUPPLEMENTARY MATERIAL A Green Approach for the Synthesis of Novel 7,11-Dihydro-6H-chromeno[3,4- e]isoxazolo[5,4-b]pyridin-6-one
Διαβάστε περισσότεραSupporting Information. Chemoselective Acylation of 2-Amino-8-quinolinol in the Generation of C2-Amides or C8-Esters
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2017 Supporting Information Chemoselective Acylation of 2-Amino-8-quinolinol in the Generation of
Διαβάστε περισσότεραHeavier chalcogenone complexes of bismuth(iii)trihalides: Potential catalysts for acylative cleavage of cyclic ethers. Supporting Information
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2015 Heavier chalcogenone complexes of bismuth(iii)trihalides: Potential catalysts for acylative
Διαβάστε περισσότεραSupporting Information
Supporting Information Co(III)-Catalyzed Synthesis of Quinazolines via C-H Activation of -Sulfinylimines and Benzimidates Fen Wang, He Wang, Qiang Wang, Songjie Yu, Xingwei Li* Dalian Institute of Chemical
Διαβάστε περισσότεραSupporting Information
Electronic Supplementary Material (ESI) for rganic Chemistry Frontiers. This journal is the Partner rganisations 2018 Palladium-catalyzed direct approach to α-cf 3 aryl ketones from arylboronic acids Bo
Διαβάστε περισσότεραSupplementary Material
Supplementary Material Efficient, mild synthesis of - unsubstituted 1,2,3- triazoles from methanolysis of 1-sulfonyl-1,2,3-triazoles Janeth Rodríguez-Florencio, Diego Martínez-tero, Marco A. García-Eleno,
Διαβάστε περισσότεραFour- and Five-membered Cobaltacycles by Regioselective Cyclometalation. of Benzylsulfide Derivatives via Co(V) intermediates
Electronic Supplementary Information for Dalton Transactions This journal is The Royal Society of Chemistry 2008 Supporting Information for: Four- and Five-membered Cobaltacycles by Regioselective Cyclometalation
Διαβάστε περισσότεραPd Catalyzed Carbonylation for the Construction of Tertiary and
Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2014 Pd Catalyzed Carbonylation for the Construction of Tertiary and Quaternary
Διαβάστε περισσότερα