Eur. J. Inorg. Chem WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim, 2007 ISSN SUPPORTING INFORMATION
|
|
|
- Ἡλί Οικονόμου
- 5 χρόνια πριν
- Προβολές:
Transcript
1 Eur. J. Inorg. Chem WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim, 2007 ISSN SUPPORTING INFORMATION Title: Synthesis of Cyclic Carbonates from Atmospheric Pressure Carbon Dioxide Using Exceptionally Active Aluminium(salen) Complexes as Catalysts Author(s): Jaisiel Meléndez, Michael North,* Riccardo Pasquale Ref. No.: I
2 Experimental details General procedure for the synthesis of catalysts 1a h Al(OEt) 3 (0.28 g, 1.72 mmol) was added to toluene (60 ml) and stirred under reflux for 1 hour. The appropriate salen ligand (1.68 mmol) dissolved in toluene (40 ml) was then added and the reaction mixture was stirred under reflux for a further 3 hours before being allowed to cool to room temperature. The solution was dried (Na 2 SO 4 ) and solvents were evaporated in vacuo to give a solid which was purified as specified below. Data for complex 1a: [S1] Yellow solid purified by washing with cold hexane. Yield 63%; [α] 20 D 548 (c= 0.11); ν max (CH 2 Cl 2 ) 2953 m, 1626 m, and 1474 cm 1 m; δ Η (CDCl 3 ) 8.35 (2H, s, CH=N), 8.15 (2H, s, CH=N), 7.52 (4H, d J 2.3 Hz, 4 x ArH), 7.07 (4H, d J 2.3 Hz, 4 x ArH), (2H, br m, CHN), (2H, br m, CHN), (16H, m, 2 x (CH 2 ) 4 ), 1.50 (36H, s, 4 x (CH 3 ) 3 ), 1.29 (36H, s, 4 x (CH 3 ) 3 ); m/z (ESI) (MH + ), 649.4, 623.4, 603.4, 569.3; Found (ESI) , C 72 H 105 N 4 O 5 Al 2 (MH + ) requires Data for complex 1b: Orange solid purified by washing with Et 2 O. Yield 63%; [α] D (c= 0.1, toluene); ν max (ATR) 2925 w, 1638 m, 1599 m, and 1573 cm 1 m; δ Η (CDCl 3 ) 8.64 (4H, s, 4 x CH=N), 8.36 (4H, s, 4 x ArH), 8.02 (4H, s, 4 x ArH), (4H, br, CHN), (16H, m, 2 x (CH 2 ) 4 ), 1.55 (36H,
3 s, 4 x (CH 3 ) 3 ); m/z (ESI) (MH + ); Found (ESI) C 56 H 69 N 8 O 13 Al 2 (MH + ) requires Data for complex 1c: [S1,S2] Yellow solid purified by washing with cold Et 2 O. Yield 50%; ν max (ATR) 2950 m, 2866 w, 1628 m, and 1538 cm 1 m; δ Η (CDCl 3 ) 8.38 (4H, s, 4 x CH=N), 7.52 (4H, d J 2.5 Hz, 4 x ArH), 7.04 (4H, d J 2.6 Hz, 4 x ArH), (4H, br, (CH 2 ) 2 ), (4H, br, (CH 2 ) 2 ), 1.30 (36H, s, 4 x (CH 3 ) 3 ), 1.55 (36H, s, 4 x (CH 3 ) 3 ); m/z (ESI) (MH + ), 664.5, 638.5, 549.4, 517.3; Found (ESI) C 64 H 93 N 4 O 5 Al 2 (MH + ) requires Data for complex 1d: [S3] The reaction was heated at reflux overnight and gave an orange powder. Yield 60%; ν max (CH 2 Cl 2 ) 2952 m, 2868 m, 1614 s, 1583 s, and 1531 cm 1 s; δ Η (CDCl 3 ) 8.66 (4H, s, 4 x CH=N), 7.43 (4H, d J 2.3 Hz, 4 x ArH), (4H, m, 4 x ArH), (8H, m, 8 x ArH), 1.43 (36H, s, 4 x (CH 3 ) 3 ), 1.32 (36H, s, 4 x (CH 3 ) 3 ); m/z (Maldi) (MH + ), 582.3, 540.4; Found (ESI) C 72 H 93 N 4 O 5 Al 2 (MH + ) requires Data for complex 1e: The reaction was heated at reflux overnight and gave a yellow powder which was purified by washing with cold Et 2 O. Yield 35%; [α] 20 D 753 (c= 0.1, CHCl 3 ); ν max (ATR) 2937 m, 2838 m, 1606 s, and 1537 cm 1 s; δ Η (CDCl 3 ) 9.87 (4H, s, 4 x CH=N), 7.18 (4H, dd J 8.9, 3.0 Hz, 4 x ArH), 7.03 (4H, d J 3.1 Hz, 4 x ArH), 6.97 (4H, d J 9.0 Hz, 4 x ArH), 3.82 (12H, s, 4 x OCH 3 ), (4H, m, 4 x CHN), (16H, m 2 x (CH 2 ) 4 ); m/z (Maldi) (MH + ), 789.3, 662.4, 407.1; Found (ESI) C 44 H 49 N 4 O 9 Al 2 (MH + ) requires Data for complex 1f: The reaction was heated at reflux overnight and gave a yellow powder which was purified by washing with cold Et 2 O. Yield 33%; [α] 20 D 381 (c= 0.1, CHCl 3 ); ν max (ATR) 2863 w, 1628 s, 1601 m, and 1537 cm 1 m; δ Η (CDCl 3 ) 8.27 (4H, s, CH=N), (4H, m, ArH), (4H, m, ArH), (4H, m, ArH), (4H, m, ArH), (4H, m, CHN), (16H, m, 2 x (CH 2 ) 4 ); m/z
4 (Maldi) (MH + ), 669.3, 364.1, 347.1; Found (ESI) C 40 H 41 N 4 O 5 Al 2 (MH + ) requires Data for complex 1g: The reaction was heated at reflux overnight and gave a yellow powder which was purified by washing with cold Et 2 O followed by chromatography on Sephadex LH50 using toluene / ethanol (1:1) as eluent. Yield 45%; [α] 20 D 372 (c= 0.1, CHCl 3 ); ν max (ATR) 2951 m, 1633 s, and 1538 cm 1 m; δ Η (CDCl 3 ) 8.28 (4H, s, 4 x CH=N), 7.29 (4H, dd J 8.1, 2.1 Hz, 4 x ArH), 7.14 (4H, d J 2.7 Hz, 4 x ArH), 6.84 (4H, d J 8.7 Hz, 4 x ArH), (4H, m, 4 x CHN), (16H, m 2 x (CH 2 ) 4 ), 1.45 (36H, s, 4 x C(CH 3 ) 3 ); m/z (Maldi) (MH + ), 893.6, 847.5, 775.4, 573.4, 459.3; Found (ESI) C 56 H 73 N 4 O 5 Al 2 (MH + ) requires Data for complex 1h: The reaction was heated at reflux overnight and gave a yellow powder which was purified by washing with cold Et 2 O followed by chromatography on Sephadex LH50 using toluene / ethanol (1:1) as eluent. Yield 30%; [α] 20 D 612 (c= 0.1, CHCl 3 ); ν max (ATR) 2949 m, 1627 s, and 1552 cm 1 m; δ Η (CDCl 3 ) 8.26 (4H, s, 4 x CH=N), 6.91 (4H, d J 3.0 Hz, 4 x ArH), 6.49 (4H, d J 3.0 Hz, 4 x ArH), 3.70 (12H, s, 4 x OCH 3 ), (4H, m, 4 x CHN), (16H, m 2 x (CH 2 ) 4 ), 1.41 (36H, s, 4 x C(CH 3 ) 3 ); m/z (Maldi) (MH + ), 876.6, 848.5, 519.3, 494.3; Found (ESI) C 60 H 81 N 4 O 9 Al 2 (MH + ) requires General procedure for the synthesis of cyclic carbonates 3a e A mixture of an epoxide 2a e (2 mmol), tetrabutylammonium bromide (0 2.5 mol-%) and the appropriate catalyst 1a h (0 2.5 mol-%) was vigorously stirred until complete dissolution occurred, then CO 2 was passed through the flask at atmospheric pressure. After being stirred at 25 o C for the time specified in Table 1 or Table 2, a sample of the reaction was analysed by 1 H NMR spectroscopy to determine the conversion, and the reaction mixture was purified by flash chromatography to give cyclic carbonate 3a e.
5 Data for styrene carbonate 3a: [S4] Conversion 62%, isolated yield 57% (Table 1: entry 9) after purification by flash chromatography (hexane / EtOAc 2:3). Mp o C; ν max (ATR) 3047 m, 3020 m, 2968 m, 2899 m, 1812 s, and 1592 cm 1 w; δ H (5H, m, ArH), 5.68 (1H, t J 8.0 Hz, PhCHO), 4.81 (1H, t J 8.5 Hz, OCH 2 ), 4.35 (1H, t J 8.4 Hz, OCH 2 ) δ C 154.9, 135.9, 129.8, 129.3, 126.0, 78.1, 71.3; m/z (EI) 164 (M +, 100), 119 (10), 105 (10). Data for propylene carbonate 3b: [S5] Reaction carried out at 0 o C, conversion 82%, isolated yield 77% (Table 2: entry 1) after purification by flash chromatography (hexane / EtOAc 4:1). ν max (neat) 2991 m, 2921 m, 1786 cm 1 s; δ H (1H, m, CHO), 4.55 (1H, t J 8.4 Hz OCH 2 ), 4.02 (1H, dd J 8.4, 7.3 Hz OCH 2 ), 1.49 (3H, d J 6.3 Hz, CH 3 ); δ C 154.5, 73.7, 70.9, 19.7; m/z (EI) 102 (M +, 100), 100 (5). Data for allylbenzene carbonate 3c: [S6] Conversion 50%, isolated yield 44% (Table 2: entry 4) after purification by flash chromatography (hexane / EtOAc 2:3). ν max (neat) 3064 w, 3031 w, 2980 w, 2920 w, 1800 cm 1 s; δ H (5H, m, ArH), 4.85 (1H, m, OCH), 4.35 (1H, t J 7.8 Hz, OCH 2 ), 4.08 (1H, dd J 8.4, 6.9 Hz, OCH 2 ), 3.06 (1H, dd J 14.1, 6.3 Hz, CH 2 Ph), 2.90 (1H, dd J 14.1, 6.3 Hz, CH 2 Ph); δ C 154.5, 134.1, 129.3, 128.9, 127.5, 76.8, 68.5, 39.6; m/z (EI), 178 (M +, 20), 91 (100). Data for hex-1-ene carbonate 3d: [S5] Conversion 90%, isolated yield 87% (Table 2: entry 6) after purification by flash chromatography (hexane / EtOAc 2:3). ν max (neat) 2960 s, 2934 s, 2874 m, 1797 cm 1 s; δ H 4.64 (1H, qd J 7.5, 5.4 Hz, OCH), 4.46 (1H, t J 7.8 Hz, OCH 2 ), 4.09 (1H, dd J 8.4, 7.2 Hz, OCH 2 ), (2H, m, CH 2 ), (4H, m, 2 x CH 2 ), 0.95 (3H, t J 7.1 Hz, CH 3 ); δ C 155.2, 77.2, 69.5, 33.7, 26.5, 22.4, 13.9; m/z (CI, NH 3 ), 162 (M+NH + 4, 100), 161 (40), 100 (10). Data for dec-1-ene carbonate 3e: [S7] Conversion 70%, isolated yield 64% (Table 2: entry 7) after purification by flash chromatography (Et 2 O). ν max (neat) 2928 s, 2857 s, 1805 cm 1 s; δ H 4.72 (1H, qd J 7.5,
6 5.7 Hz, OCH), 4.54 (1H, t J 8.1 Hz, OCH 2 ), 4.09 (1H, t J 7.5 Hz, OCH 2 ), (2H, m, CH 2 ), (12H, m, 6 x CH 2 ), 0.90 (3H, t J 6.6 Hz, CH 3 ); δ C 155.2, 77.1, 69.5, 34.0, 31.9, 29.4, 29.2, 29.1, 24.5, 22.7, 14.2; m/z (EI), 162 (M +, 8), 95 (38), 67 (100). References [S1] a) S.J. Dzugan, V.L. Goedken, Inorg. Chem. 1986, 25, ; b) G.M. Sammis, E.N. Jacobsen, J. Am. Chem. Soc. 2003, 125, ; c) M.S. Taylor, E.N. Jacobsen, J. Am. Chem. Soc. 2003, 125, ; d) I.T. Raheem, S.N. Goodman, E.N. Jacobsen, J. Am. Chem. Soc. 2004, 126, ; e) G.M. Sammis, H. Danjo, E.N. Jacobsen, J. Am. Chem. Soc. 2004, 126, ; f) C.D. Vanderwal, E.N. Jacobsen, J. Am. Chem. Soc. 2004, 126, ; g) M. Gandelman, E.N. Jacobsen, Angew. Chem. Int. Ed. 2005, 44, ; h) M.S. Taylor, D.N. Zalatan, A.M. Lerchner, E.N. Jacobsen, J. Am. Chem. Soc. 2005, 127, ; i) E.P. Balskus, E.N. Jacobsen, J. Am. Chem. Soc. 2006, 128, [S2] D. Rutherford, D.A. Atwood, Organometallics 1996, 15, [S3] Y. Wang, S. Bhandari, S. Parkin, D.A. Atwood, J. Organomet. Chem. 2004, 689, [S4] T. Iida, T. Itaya, Tetrahedron 1993, 49, [S5] J.-W. Huang, M. Shi, J. Org. Chem. 2003, 68, [S6] R.L. Paddock, Y. Hiyama, J.M. McKay, S.T. Nguyen, Tetrahedron Lett. 2004, 45, [S7] A.G.M. Barrett, P.A. Prokopiou, D.H.R. Barton, J. Chem. Soc., Perkin Trans ,
Site-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,
Supplementary 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
Supplementary 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
Hiyama Cross-Coupling of Chloro-, Fluoroand Methoxy- pyridyl trimethylsilanes : Room-temperature Novel Access to Functional Bi(het)aryl
Hiyama Cross-Coupling of Chloro-, Fluoroand Methoxy- pyridyl trimethylsilanes : Room-temperature Novel Access to Functional Bi(het)aryl Philippe Pierrat, Philippe Gros* and Yves Fort Synthèse Organométallique
Supporting 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
Supporting 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
and 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
Copper-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
Supporting 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
Electronic 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
Supporting 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,
Room 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
Supporting 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
Free Radical Initiated Coupling Reaction of Alcohols and. Alkynes: not C-O but C-C Bond Formation. Context. General information 2. Typical procedure 2
Free Radical Initiated Coupling Reaction of Alcohols and Alkynes: not C-O but C-C Bond Formation Zhongquan Liu,* Liang Sun, Jianguo Wang, Jie Han, Yankai Zhao, Bo Zhou Institute of Organic Chemistry, Gannan
Supporting 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
Direct 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
Metal-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:
Highly 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
Supporting 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
Copper-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
Tributylphosphine-Catalyzed Cycloaddition of Aziridines with Carbon Disulfide and Isothiocyanate
upporting Information Tributylphosphine-Catalyzed Cycloaddition of Aziridines with Carbon Disulfide and Isothiocyanate Jing-Yu Wu, Zhi-Bin Luo, Li-Xin Dai and Xue-Long Hou* a tate Key Laboratory of Organometallic
Novel and Selective Palladium-Catalyzed Annulation of 2-Alkynylphenols to Form 2-Substituted 3-Halobenzo[b]furans. Supporting Information
![Novel and Selective Palladium-Catalyzed Annulation of 2-Alkynylphenols to Form 2-Substituted 3-Halobenzo[b]furans. Supporting Information](/thumbs/64/50937700.jpg "Novel and Selective Palladium-Catalyzed Annulation of 2-Alkynylphenols to Form 2-Substituted 3-Halobenzo[b]furans. Supporting Information")
Novel and Selective Palladium-Catalyzed Annulation of 2-Alkynylphenols to Form 2-Substituted 3-Halobenzo[b]furans Liang Yun, Shi Tang, Xu-Dong Zhang, Li-Qiu Mao, Ye-Xiang Xie and Jin-Heng Li* Key Laboratory
Synthesis 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
9-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
Enantioselective Organocatalytic Michael Addition of Isorhodanines. to α, β-unsaturated Aldehydes
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,
Supporting Information. Synthesis and biological evaluation of nojirimycin- and
Supporting Information for Synthesis and biological evaluation of nojirimycin- and pyrrolidine-based trehalase inhibitors Davide Bini 1, Francesca Cardona 2, Matilde Forcella 1, Camilla Parmeggiani 2,3,
Supporting Information
Supporting Information 2017 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim Convenient and General Zinc-Catalyzed Borylation of Aryl Diazonium Salts and Aryltriazenes under Mild Conditions
Supporting 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, *
Supporting Information
Supporting Information Wiley-VCH 2008 69451 Weinheim, Germany Ligand-Free Pd-Catalyzed Highly Selective Arylation of Allylic Esters with Retention of the Traditional Leaving Group (Supporting Information)
Lewis Acid Catalyzed Propargylation of Arenes with O-Propargyl Trichloroacetimidate: Synthesis of 1,3-Diarylpropynes
Supporting Information for Lewis Acid Catalyzed Propargylation of Arenes with O-Propargyl Trichloroacetimidate: Synthesis of 1,3-Diarylpropynes Changkun Li and Jianbo Wang* Beijing National Laboratory
A 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
Supporting 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.
Rh(III)-Catalyzed C-H Amidation with N-hydroxycarbamates: A. new Entry to N-Carbamate Protected Arylamines
Rh(III)-Catalyzed C-H Amidation with N-hydroxycarbamates: A new Entry to N-Carbamate Protected Arylamines Bing Zhou,* Juanjuan Du, Yaxi Yang,* Huijin Feng, Yuanchao Li Shanghai Institute of Materia Medica,
Supporting 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
Supporting 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
Supporting 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
Supporting 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
Electronic 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
Chiral 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
Divergent 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,
Supporting Information
Supporting Information Wiley-VC 007 9 Weinheim, Germany ew ear Infrared Dyes and Fluorophores Based on Diketopyrrolopyrroles Dipl.-Chem. Georg M. Fischer, Dipl.-Chem. Andreas P. Ehlers, Prof. Dr. Andreas
Fluorinative 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
The Free Internet Journal for Organic Chemistry
The Free Internet Journal for Organic Chemistry Paper Archive for Organic Chemistry Arkivoc 2018, part iii, S1-S6 Synthesis of dihydropyranones and dihydropyrano[2,3- d][1,3]dioxine-diones by cyclization
Supporting Information
Supporting Information Wiley-VCH 10 69451 Weinheim, Germany Selective and Bond Formations through Copper- Catalyzed Aerobic xidative Dehydrogenative Couplings of H-hosphonates Yongbo Zhou, Shuangfeng Yin,
Supporting Information. Copyright Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2006
Copyright Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2006 Silver-Catalyzed Asymmetric Synthesis of 2,3-Dihydrobenzofurans: A New Chiral Synthesis of Pterocarpans Leticia Jiménez-González, Sergio
Asymmetric Synthesis of New Chiral β-amino Acid Derivatives by Mannich-type Reactions of Chiral N- Sulfinyl Imidates with N-Tosyl Aldimines
Asymmetric Synthesis of New Chiral β-amino Acid Derivatives by Mannich-type Reactions of Chiral N- Sulfinyl Imidates with N-yl Aldimines Filip Colpaert, Sven Mangelinckx, and Norbert De Kimpe Department
First 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
Synthesis 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,
Supporting 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
Supporting 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
gem-dichloroalkenes for the Construction of 3-Arylchromones
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2015 Pd(OAc)2/S=PPh3 Accelerated Activation of gem-dichloroalkenes for the Construction of 3-Arylchromones
Regioselectivity 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
Supporting 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
Supporting information
Electronic upplementary Material (EI) for New Journal of Chemistry. This journal is The Royal ociety of Chemistry and the Centre National de la Recherche cientifique 7 upporting information Lipase catalyzed,-addition
Supporting Information. for. Highly Selective Hydroiodation of Alkynes Using. Iodine-Hydrophosphine Binary System
Supporting Information for Highly Selective Hydroiodation of Alkynes Using Iodine-Hydrophosphine Binary System Shin-ichi Kawaguchi and Akiya Ogawa * Department of Applied Chemistry, Graduate School of
Supplementary Material
Supplementary Material Control experiments S2 Characterization data for the products S2-S7 References S8 MR spectra for the products S9-S28 S1 Control experiments 2a (99.5 mg, 0.5 mmol), I 2 (50.8 mg,
Supporting Information
Supporting Information Siloxy(trialkoxy)ethene Undergoes Regioselective [2+2] Cycloaddition to Ynones and Ynoates en route to Functionalized Cyclobutenediones Shin Iwata, Toshiyuki Hamura, and Keisuke
Supporting Information. Synthesis and biological evaluation of 2,3-Bis(het)aryl-4-azaindoles Derivatives as protein kinases inhibitors
Supporting Information Synthesis and biological evaluation of 2,3-Bis(het)aryl-4-azaindoles Derivatives as protein kinases inhibitors Frédéric Pin, a Frédéric Buron, a Fabienne Saab, a Lionel Colliandre,
Peptidomimetics as Protein Arginine Deiminase 4 (PAD4) Inhibitors
Peptidomimetics as Protein Arginine Deiminase 4 (PAD4) Inhibitors Andrea Trabocchi a, icolino Pala b, Ilga Krimmelbein c, Gloria Menchi a, Antonio Guarna a, Mario Sechi b, Tobias Dreker c, Andrea Scozzafava
Supplementary Material for Synthesis of Compact Multidentate Ligands to Prepare Stable Hydrophilic Quantum Dot Fluorophores
Supplementary Material for Synthesis of Compact Multidentate Ligands to Prepare Stable Hydrophilic Quantum Dot Fluorophores 5-[1,2]-Dithiolan-3-yl-pentanoic acid 2-[2-(2-{2-[2-(2-hydroxy-ethoxy)-ethoxy]-ethoxy}-
Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2008
Palladium(0)-catalyzed direct cross-coupling reaction of allylic alcohols with aryland alkenylboronic acids Hirokazu Tsukamoto, Tomomi Uchiyama, Takamichi Suzuki and Yoshinori Kondo Graduate School of
Supporting Information
S1 Supporting Information Synthesis of 2-Arylated Hydroxytyrosol Derivatives via Suzuki-Myaura Cross-Coupling Roberta Bernini, a Sandro Cacchi, b* Giancarlo Fabrizi, b* Eleonora Filisti b a Dipartimento
Supporting Information
Supporting Information Rhodium-catalyzed Intramolecular Dehydrogenative Aryl Aryl Coupling Using Air as Terminal Oxidant Hannah Baars, 1,2 Yuto Unoh, 1 Takeshi Okada, 1 Koji Hirano, 1 Tetsuya Satoh,* 1,3
A straightforward metal-free synthesis of 2-substituted thiazolines in air
Electronic Supplementary Material (ESI) for Green Chemistry. This journal is The Royal Society of Chemistry 2015 Supporting Information for A straightforward metal-free synthesis of 2-substituted thiazolines
Sotto, 8; Perugia, Italia. Fax: ; Tel: ;
ELECTRONIC SUPPORTING INFORMATION Ermal Ismalaj a, Giacomo Strappaveccia a, Eleonora Ballerini a, Fausto Elisei a, Oriana Piermatti a, Dmitri Gelman b, Luigi Vaccaro a a CEMIN - Dipartimento di Chi mica,
Supporting Information
Supporting Information An Approach to 3,6-Disubstituted 2,5-Dioxybenzoquinones via Two Sequential Suzuki Couplings. Three-step Synthesis of Leucomelone Xianwen Gan, Wei Jiang, Wei Wang,,,* Lihong Hu,,*
Supporting Information for
Supporting Information for A ovel Synthesis of luorinated Pyrazoles via Gold(I)-Catalyzed Tandem Aminofluorination of Alkynes in the Presence of Selectfluor Jianqiang Qian, Yunkui Liu,* Jie Zhu, Bo Jiang,
Supplementary 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
Supporting Information
Supporting Information Metal-catalyzed Stereoselective and Protecting-group-free Synthesis of 1,2-cis-Glycosides Using 4,6-Dimethoxy-1,3,5-triazin-2-yl Glycosides as Glycosyl Donors Tomonari Tanaka,* 1
ESI for. A simple and efficient protocol for the palladium-catalyzed. ligand-free Suzuki reaction at room temperature in aqueous DMF.
ESI for A simple and efficient protocol for the palladium-catalyzed ligand-free Suzuki reaction at room temperature in aqueous DMF Chun Liu,* Qijian i, Fanying Bao and Jieshan Qiu State Key Laboratory
Supporting Information
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2017 Modular Synthesis of Propargylamine Modified Cyclodextrins by a Gold(III)-catalyzed Three Component
Effect of uridine protecting groups on the diastereoselectivity
Supporting Information for Effect of uridine protecting groups on the diastereoselectivity of uridine-derived aldehyde 5 -alkynylation Raja Ben Othman, Mickaël J. Fer, Laurent Le Corre, Sandrine Calvet-Vitale*
SUPPORTING INFORMATION. 1. General... S1. 2. General procedure for the synthesis of compounds 3 and 4 in the absence of AgOAc...
SUPPORTING INFORMATION Table of contents 1. General.... S1 2. General procedure for the synthesis of compounds 3 and 4 in the absence of AgOAc... S2 3. General procedure for the synthesis of compounds
Supplementary Information
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 215 Supplementary Information Zinc monoglycerolate as a catalyst for the conversion of 1,3- and
Copper-promoted hydration and annulation of 2-fluorophenylacetylene derivatives: from alkynes to benzo[b]furans and benzo[b]thiophenes
![Copper-promoted hydration and annulation of 2-fluorophenylacetylene derivatives: from alkynes to benzo[b]furans and benzo[b]thiophenes](/thumbs/61/45469742.jpg "Copper-promoted hydration and annulation of 2-fluorophenylacetylene derivatives: from alkynes to benzo[b]furans and benzo[b]thiophenes")
Supporting Information for Copper-promoted hydration and annulation of 2-fluorophenylacetylene derivatives: from alkynes to benzo[b]furans and benzo[b]thiophenes Yibiao Li* 1, Liang Cheng 1, Xiaohang Liu
using metal-organic framework Cu-MOF-74 as an efficient heterogeneous catalyst Hanh T. H. Nguyen, Oanh T. K. Nguyen, Thanh Truong *, Nam T. S.
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2016 Synthesis of imidazo[1,5-a]pyridines via oxidative amination of C(sp 3 )-H bond under air using
Pd 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
Supporting Information
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2014 Supporting Information A Convenient and Efficient Synthesis of Glycals by Zinc Nanoparticles
Supporting Information for Iron-catalyzed decarboxylative alkenylation of cycloalkanes with arylvinylic carboxylic acids via a radical process
Supporting Information for Iron-catalyzed decarboxylative alkenylation of cycloalkanes with arylvinylic carboxylic acids via a radical process Jincan Zhao 1, Hong Fang 1, Jianlin Han* 1,2 and Yi Pan* 1
Eco-friendly synthesis of diverse and valuable 2-pyridones by catalyst- and solvent-free thermal multicomponent domino reaction
Electronic Supplementary Material (ESI) for Green Chemistry. This journal is The Royal Society of Chemistry 2015 SUPPRTIG IFRMATI Eco-friendly synthesis of diverse and valuable 2-pyridones by catalyst-
Direct 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](/thumbs/87/95187440.jpg "Direct 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
Aminofluorination of Fluorinated Alkenes
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2018 Synthesis of ɑ CF 3 and ɑ CF 2 H Amines via Aminofluorination of Fluorinated Alkenes Ling Yang,
Supporting Information. Table of Contents. II. Experimental procedures. II. Copies of 1H and 13C NMR spectra for all compounds
Electronic upplementary Material (EI) for rganic & Biomolecular Chemistry. This journal is The Royal ociety of Chemistry 2017 Laboratoire de Méthodologie et ynthèse de Produit aturels. Université du Québec
Supporting Information. Consecutive hydrazino-ugi-azide reactions: synthesis of acylhydrazines bearing 1,5- disubstituted tetrazoles
Supporting Information for Consecutive hydrazino-ugi-azide reactions: synthesis of acylhydrazines bearing 1,5- disubstituted tetrazoles Angélica de Fátima S. Barreto*, Veronica Alves dos Santos, and Carlos
Supporting Information. Copyright Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2007
Supporting Information Copyright Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2007 Copyright Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2006 Supporting Information for High-Throughput Substrate
Palladium-Catalyzed C H Monoalkoxylation of α,β-unsaturated Carbonyl Compounds
Supporting Information Palladium-Catalyzed C H Monoalkoxylation of α,β-unsaturated Carbonyl Compounds Yasunari Monguchi,* Kouki Kunishima, Tomohiro Hattori, Tohru Takahashi, Yuko Shishido, Yoshinari Sawama,
Supporting Information
Supporting Information Copyright Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2014 A Family of Click Nucleosides for Metal-Mediated Base Pairing: Unravelling the Principles of Highly Stabilizing Metal-Mediated
Oxyhalogenation 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
SUPPORTING INFORMATION
Eur. J. Org. Chem. 2006 WILEY-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2006 ISSN 1434 193X SUPPORTING INFORMATION Title: Sulfonamide Ligands Attained Through Opening of Saccharin Derivatives Author(s):
Construction 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
Supporting 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
Supporting 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,
Supporting Information
Supporting Information Wiley-VCH 2014 69451 Weinheim, Germany Copper-Catalyzed Coupling of Oxime Acetates with Sodium Sulfinates: An Efficient Synthesis of Sulfone Derivatives** Xiaodong Tang, Liangbin
Supporting Information
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2017 Supporting Information 1. General experimental methods (S2). 2. Table 1: Initial studies (S2-S4).
Supporting Information
Supporting Information Copyright Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2010 A Highly Effective Bis(sulfonamide) Diamine Ligand: A Unique Chiral Skeleton for the Enantioselective Cu-Catalyzed
Supporting Information for Synthesis of Fused N-Heterocycles via Tandem C-H Activation
This journal is The Royal Society of Chemistry 212 Supporting Information for Synthesis of Fused -Heterocycles via Tandem C-H Activation Ge Meng, Hong-Ying iu, Gui-Rong Qu, John S. Fossey, Jian-Ping Li,*
Copper-mediated radical cross-coupling reaction of 2,2-dichloro-1,1,1-trifluoroethane (HCFC-123) with phenols or thiophenols. Support Information
Copper-mediated radical cross-coupling reaction of 2,2-dichloro-1,1,1-trifluoroethane (HCFC-123) with phenols or thiophenols Dr. Xiao un Tang and Prof. Qing un Chen* Key Laboratory of Organofluorine Chemistry,
Supporting 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 *
Supporting Information
1 upporting Information Rhodium(III)-Catalyzed rtho Halogenations of N-Acylsulfoximines and ynthetic Applications toward Functionalized ulfoximine Derivatives Ying Cheng, Wanrong Dong, Kanniyappan Parthasarathy,
Acrylate Esters for Synthesis of Chiral γ-lactams and Amino Acids
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2015 Supplementary Information for: Highly Efficient Asymmetric Hydrogenation