Supporting Information
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- Οινώνη Ζάππας
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1 Supporting Information Arylalkene Synthesis via Decarboxylative Cross-Coupling of Alkenyl Halides Jie Tang and Lukas J. Gooßen* B Chemie-rganische Chemie, TU Kaiserslautern, Erwin-Schrödinger-Str. Geb., Kaiserslautern, Germany goossen@chemie.uni-kl.de List of Contents General method and screening reaction conditions.s General procedure for the synthesis of potassium carboxylates.. S General procedure for the decarboxylative coupling.. S Synthesis and characterization of the corresponding products... S References.. S NMR Spectra... S0 S
2 General method and Screening reaction conditions Chemicals and solvents were either purchased (puriss p.a.) from commercial supplier or purified by standard techniques. All reactions, if not stated otherwise, were performed in oven-dried glassware under a nitrogen atmosphere containing a teflon-coated stirrer bar and dry septum. Reaction media were saturated with Argon to exclude atmospheric oxygen. All reactions were monitored by GC using tetradecane as an internal standard. Response factors of the products with regard to tetradecane were obtained experimentally by analyzing known quantities of the substances. GC analyses were carried out using an HP- capillary column (Phenyl methyl siloxane, 0 m x 0 x 0., 00/.-0-00/, min at 0 C, heating rate 0 C/min, or 0 min at 00 C). Column chromatography was performed using a Combi lash Companion-Chromatography-System (Isco-Systems) and RediSep packed columns ( g). NMR spectra were recorded at ambient temperature using CDCl as solvent, with proton, carbon at 00/00, 00/0 MHz, respectively. Mass spectral data were acquired on a Varian GC-MS Saturn 00 T. The ionization was achieved by EI AGC. High resolution mass spectra were acquired on a Waters GCT Premium. Infrared spectra were recorded on Perkin Elmer Spectrum 00 T-IR Spectrometer with Universal ATR Sampling Accessory. The alkenyl bromides/chlorides a, b, c, e, f, g, h, i, j, a, c, j were prepared according to the literature procedures and identified by comparison of their spectra with those of authentic samples. d was purchased from Aldrich and used as received. The aromatic carboxylates were prepared from the corresponding aromatic carboxylic acids following the procedures below and were directly used. S
3 Table. Screening conditions for decarboxylative cross-coupling reaction a CK entry Cu-source Pd-source ligand solvent T ( C) yield (%) b CuBr Pd(acac) - NMP/quin.=/ 0 - NMP/quin.=/ - NMP/quin.=/ - NMP/Mes.=/ - NMP/Mes.=/ - NMP/Mes.=/ dppm Cu CuCN 0 CuI CuAc CuCl Pd(Ac) Pd(TA) Pdl PdBr PdCl Pd(dba) Pd(PPh ) 0 Pd( -acac) PPh PCy P(t-Bu) P(-furyl) P(p-Tol) P(p-MePh) P(o-Tol) P(-naph) a Reaction conditions: a (0. mmol), a (0. mmol), Pd-source ( mol %), phosphine ligand (.0 mol %), Cu-source (0 mol %),, 0-phenanthroline (0 mol %), h. b Yields determined by GC analysis using n-tetradecane as the internal standard. c dppm = bis(diphenyl-phosphino)methane; quin. = quinoline; Mes. = mesitylene; NMP = N-methylpyrrolidone. a + N Br solvent, T N a [Pd] / ligand [Cu] /,0-phenanthroline aa S
4 General procedure for the synthesis of potassium carboxylate salts A 0 ml, two-necked, round-bottomed flask was charged with the carboxylic acid (0.0 mmol) and ethanol (0.0 ml). To this, a solution of potassium t-butoxide (. g, 0.0 mmol) in ethanol (0.0 ml) was added dropwise over h. After complete addition, the reaction mixture was stirred for another h at room temperature. A gradual formation of a white precipitate was observed. The resulting solid was collected by filtration washed sequentially with ethanol ( 0.0 ml) and cold (0 C) diethyl ether (0.0 ml), and dried in vacuum to provide the corresponding potassium salts of the carboxylic acids. General procedure for the decarboxylative coupling An oven-dried, nitrogen-flushed 0 ml crimp cap vessel was charged with the potassium carboxylate (0. mmol,. equiv.), Pd( -acac) (. mg, 0.00 mmol, mol %), tri--naphthylphosphine (. mg, 0.0 mmol,.0 mol %), copper(i) chloride (. mg, 0.0 mmol, 0 mol %),, 0-Phenanthroline (. mg, 0.0 mmol, 0 mol %) and alkenyl bromide (0. mmol). A degassed mixture of NMP ( ml) and mesitylene ( ml) was added via syringe. The resulting solution was then stirred at 0 ºC for h. After the reaction was complete, the mixture was cooled to room temperature, diluted with sat. NaHC and extracted with ethyl acetate ( 0 ml). The combined organic layers were washed with water and brine, dried over MgS, filtered, and concentrated in vacuo. The residue was purified by column chromatography (Si, ethyl acetate/hexane gradient) yielding the corresponding product. S
5 Synthesis and characterization of the corresponding products N -cyclohexenyl--nitrobenzene (aa) [CAS: --] Compound aa was prepared following the general method from potassium -nitrobenzoate (a) ( mg, 0. mmol) and -bromocyclohex--ene (a) ( mg, ul, 0. mmol) in a mixture of NMP ( ml) and mesitylene ( ml). Compound aa was isolated by column chromatography as a yellow liquid ( mg, %). H NMR (00 MHz, CDCl ): δ =.0 (dd, J =.0,. Hz, H),. (td, J =.,. Hz, H),.-. (m, H),. (dd, J =.,. Hz, H),.-. (m, H),.-. (m, H),.-. (m, H),.-. (m, H),.-. (m, H); C NMR (CDCl, 00 MHz): δ =.,.,.,., 0.,.,.,.,.,.0,.,. ppm; MS (EI, 0 ev) m/z (%): 0 () [M+], (), (00), 0 (), (), (). N -cyclohexenyl--fluoro--nitrobenzene (ba) Compound ba was prepared following the general method from potassium -nitro--fluoro-benzoate (b) ( mg, 0. mmol) and -bromocyclohex--ene (a) ( mg, ul, 0. mmol) in a mixture of NMP ( ml) and mesitylene ( ml). Compound ba was isolated by column chromatography as a yellow liquid ( mg, %). H NMR (00 MHz, CDCl ): δ =. (dd, J =.,. Hz, H),.0-.0 (m, H),. (dd, J =.,. Hz, H),.-. (m, H),.-. (m, H),.-. (m, S
6 H), -. (m, H),.-. (m, H); C NMR (CDCl, 00 MHz): δ =.,.,. (d, J =. Hz, C),.,.,. (d, J = 0 Hz, C),. (d, J = Hz, C),. (d, J = Hz, C),.,.,.,. ppm; IR: v =,,, 0,,,, cm - ; MS (EI, 0 ev) m/z (%): () [M+], 0 (), (00), (), (), 0 (), (). EI-HRMS m/z calcd. for C H N :, found: N -cyclohexenyl--methoxy--nitrobenzene (ca) Compound ca was prepared following the general method from potassium -nitro--methoxyl-benzoate (c) ( mg, 0. mmol) and -bromocyclohex--ene (a) ( mg, ul, 0. mmol) in a mixture of NMP ( ml) and mesitylene ( ml). Compound ca was isolated by column chromatography as a yellow liquid (0 mg, %). H NMR (00 MHz, CDCl ): δ =. (d, J =.0 Hz, H),. (dd, J =.0,. Hz, H),. (d, J =. Hz, H),.-.0 (m, H),. (s, H),.-. (m, H),.-. (m, H),.-. (m, H); C NMR (CDCl, 00 MHz): δ =.,.,.,.00,.0,.,.,.,.0,.,.,.,. ppm; IR: v =,,,,,,, 0, 0, 0, cm - ; MS (EI, 0 ev) m/z (%): () [M+], (), (00), 0 (), 0 (), (). EI-HRMS m/z calcd. for C H N :.0, found:.0 S
7 N -cyclohexenyl--methyl--nitrobenzene (da) Compound da was prepared following the general method from potassium -nitro--methyl-benzoate (d) ( mg, 0. mmol) and -bromocyclohex--ene (a) ( mg, ul, 0. mmol) in a mixture of NMP ( ml) and mesitylene ( ml). Compound da was isolated by column chromatography as a yellow liquid ( mg, %). H NMR (00 MHz, CDCl ): δ =.0 (t, J =.0 Hz, H),. (d, J =. Hz, H),.0 (dt, J =., 0. Hz, H),.0-. (m, H),. (s, H),.-. (m, H),.-.0 (m, H),.-.0 (m, H),.-.0 (m, H); C NMR (CDCl, 00 MHz): δ = 0.,.0,.,.,.,.,.,.,.,.,.,.,. ppm; IR: v =, 0,,,,, 0,,, cm - ; MS (EI, 0 ev) m/z (%): () [M+], 00 (), (00), (), 0 (0), (). EI-HRMS m/z calcd. for C H N :.0, found:. N -cyclohexenyl--methyl--nitrobenzene (ea) Compound ea was prepared following the general method from potassium -nitro--methyl-benzoate (e) ( mg, 0. mmol) and -bromocyclohex--ene (a) ( mg, ul, 0. mmol) in a mixture of NMP ( ml) and mesitylene ( ml). Compound ea was isolated by column chromatography as a yellow liquid ( mg, %). S
8 H NMR (00 MHz, CDCl ): δ =. (m, H),. (dd, J =., 0. HZ, H),. (t, J =.0 HZ, H),.-. (m, H),.0-. (m, H),.0 (s, H),.-. (m, H),.-. (m, H); C NMR (CDCl, 00 MHz): δ =.,.,.,.,.,.0,.0, 0.,.0,.,.,.,. ppm; IR: v = 0,,,,,,,,, cm - ; MS (EI, 0 ev) m/z (%): () [M+], 00 (), (00), 0 (), (0), (), (). EI-HRMS m/z calcd. for C H N :.0, found:.. CMe -(-cyclohexenylphenyl)ethanone (fa) Compound fa was prepared following the general method from potassium -acetylbenzoate (f) ( mg, 0. mmol) and -bromocyclohex--ene (a) ( mg, ul, 0. mmol) in a mixture of NMP ( ml) and mesitylene ( ml). Compound fa was isolated by column chromatography as a yellow liquid ( mg, %). H NMR (00 MHz, CDCl ): δ =. (dd, J =.,. Hz, H),.0 (td, J =.0,. Hz, H),.-. (m, H),.-.0 (m, H),. (s, H),.-. (m, H),.-. (m, H),.-. (m, H),.-. (m, H); C NMR (CDCl, 00 MHz): δ = 0.,., 0.0,., 0.,.,.,.,., 0.0,.,.,.,. ppm; IR: v = 0,,,,,,,, cm - ; MS (EI, 0 ev) m/z (%): 00 () [M+], (00), (), (), (0), (), (). EI-HRMS m/z calcd. for C H : 00.0, found: 00.. S
9 -cyclohexenyl-, -dimethoxybenzene (ga) Compound ga was prepared following the general method from potassium, -dimethoxybenzoate (g) ( mg, 0. mmol) and -bromocyclohex--ene (a) ( mg, ul, 0. mmol) in a mixture of NMP ( ml) and mesitylene ( ml). Compound ga was isolated by column chromatography as a yellow liquid ( mg, %). H NMR (00 MHz, CDCl ): δ =. (t, J =. Hz, H),. (d, J =. Hz, H),.-. (m, H),. (s, H),.-. (m, H),.-.(m, H); C NMR (CDCl, 00 MHz): δ =. (C),.,.,.,., 0. (C),. (C),.,.,.0,. ppm; IR: v = 00,,,,,,,, 0,, cm - ; MS (EI, 0 ev) m/z (%): (00) [M+], 0 (), 0 (), (), (), (), (). EI-HRMS m/z calcd. for C H :.0, found:.0. -cyclohexenyl--methoxybenzene (ha) [CAS: --0] Compound ha was prepared following the general method from potassium -methoxybenzoate (h) ( mg, 0. mmol) and -bromocyclohex--ene (a) ( mg, ul, 0. mmol) in a mixture of NMP ( ml) and mesitylene ( ml). Compound ha was isolated by column chromatography as a yellow liquid ( mg, %). H NMR (00 MHz, CDCl ): δ =. (td, J =. Hz, H),. (dd, J =.,. Hz, H),. (td, J =. Hz, H),. (d, J =.0 Hz, H),.0-. (m, H),. (s, H),.0-. (m, H),.-.0 (m, H),.-. (m, H); S
10 C NMR (CDCl, 00 MHz): δ =.,.,,.,.,., 0.0, 0.,.,.,.,.0,. ppm; IR: v = 0,,,,,,,, 0, cm - ; MS (EI, 0 ev) m/z (%): (00) [M+], (), (), (0), (), (). -cyclohexenylnaphthalene (ia) [CAS: 0--] Compound ia was prepared following the general method from potassium -naphthoate (i) ( mg, 0. mmol) and -bromocyclohex--ene (a) ( mg, ul, 0. mmol) in a mixture of NMP ( ml) and mesitylene ( ml). Compound ia was isolated by column chromatography as a yellow liquid ( mg, %). H NMR (00 MHz, CDCl ): δ =.0-.0 (m, H),.-. (m, H),. (d, J =. Hz, H),.-. (m, H),. (dd, J =.0,. Hz, H),.-. (m, H),.-. (m, H),.-. (m, H),.-. (m, H),.-. (m, H); C NMR (CDCl, 00 MHz): δ =.0,.,.,.,.,.,.,.,.,.,.,.0,,.,.,. ppm; IR: v = 0,,,,,,,,,,, cm - ; MS (EI, 0 ev) m/z (%): 0 (00) [M+], (), (), (), (), (). S -cyclohexenylbenzo[b]thiophene (ja) Compound ja was prepared following the general method from potassium benzo[b]thiophene--carboxylate (j) ( mg, 0. mmol) and -bromocyclohex--ene (a) ( mg, ul, 0. mmol) in a mixture of NMP ( ml) and mesitylene ( ml). Compound ja was isolated by column chromatography as a S0
11 yellow liquid (0 mg, %). H NMR (00 MHz, CDCl ): δ =.-. (m, H),. (dd, J =.0,. Hz, H),.-. (m, H),. (s, H),.-. (m, H),.-.0 (m, H),.0-. (m, H),.- (m, H),.-. (m, H); C NMR (CDCl, 00 MHz) δ =., 0.,.,.,.0,.0,.0,.,.,.0,.,.0,.,.0 ppm; IR: v = 0,,,,,,,,, cm - ; MS (EI, 0 ev) m/z (%): (00) [M+], (), (), (), (), 0 (). EI-HRMS m/z calcd. for C H S:.0, found:.0. N -cyclohexenyl--methyl-h-indole (ka) Compound ka was prepared following the general method from potassium -methyl-h-indole--carboxylate (k) ( mg, 0. mmol) and -bromocyclohex--ene (a) ( mg, ul, 0. mmol) in a mixture of NMP ( ml) and mesitylene ( ml). Compound ka was isolated by column chromatography as a yellow liquid ( mg, %). H NMR (00 MHz, CDCl ): δ =.-.0 (m, H),. (dd, J =., Hz, H),.-. (m, H),.-. (m, H),.0 (s, H),.-. (m, H),. (s, H),.-. (m, H),.-. (m, H),.-. (m, H),.-. (m, H); C NMR (CDCl, 00 MHz): δ =.,.,.,.,.,., 0.,., 0.,.0,.,.,.,.,. ppm; IR: v = 0,,,,,,,, cm - ; MS (EI, 0 ev) m/z (%): (00) [M+], (), (), (), (), (). EI-HRMS m/z calcd. for C H N:., found:.. S
12 -(-fluorophenyl)-,-dihydronaphthalene (lh) Compound lh was prepared following the general method from potassium -fluorobenzoate (l) (0 mg, 0. mmol) and -bromo-, -dihydronaphthalene (h) (0 mg, 0. mmol) in a mixture of NMP ( ml) and mesitylene ( ml). Compound lh was isolated by column chromatography as a colourless liquid (0 mg, %). H NMR (00 MHz, CDCl ): δ =. (td, J =.,.0 Hz, H),.-. (m, H),.-.0 (m, H),. (s, H),.00-. (m, H),.-. (m, H); C NMR (CDCl, 00 MHz): δ =.,.,. (d, J =. Hz, C),.,.,. (d, J =.0 Hz, C),. (d, J =.0 Hz, C),.0,.,.0 (d, J =.0 Hz, C),.,.0 (d, J =. Hz, C),.0 (d, J =.0 Hz, C),. (d, J =.0 Hz, C),.,. (d, J =. Hz, C) ppm; IR: v = 0, 0,,,,,,,, cm - ; MS (EI, 0 ev) m/z (%): (00) [M+], 0 (), (), (), 0 (). EI-HRMS m/z calcd. for C H :.00, found:.000. C -(-(trifluoromethyl)phenyl)-,-dihydronaphthalene (mh) Compound mh was prepared following the general method from potassium -(trifluoromethyl)benzoate (m) (0 mg, 0. mmol) and -bromo-,-dihydronaphthalene (h) (0 mg, 0. mmol) in a mixture of NMP ( ml) and mesitylene ( ml). Compound mh was isolated by column chromatography as a yellow liquid ( mg, %). H NMR (00 MHz, CDCl ): δ =. (d, J =. Hz, H),. (t, J =.0 Hz, H), S
13 . (t, J =.0 Hz, H),. (d, J =.0 Hz, H),.-.0 (m, H),.-.0 (m, H),. (s, H),.00 (t, J =. Hz, H),. (t, J =.0 Hz, H); NMR (00 MHz, CDCl ): d = -. ppm; C NMR (CDCl, 00 MHz): δ =. (q, J =.0 Hz, C),.0,.,.0,., 0.,.,.,.,. (q, J =. Hz, C),.0,.,.,. (q, J =. Hz, C),. (d, J = Hz, C),. (q, J =. Hz, C),. ppm; IR: v =, 0,,,,,, 0,, 0, cm - ; MS (EI, 0 ev) m/z (%): (00) [M+], (), (), (), (), 0 (). EI-HRMS m/z calcd. for C H :.0, found:.0. -(perfluorophenyl)-,-dihydronaphthalene (nh) Compound nh was prepared following the general method from potassium perfluorobenzoate (n) ( mg, 0. mmol) and -bromo-, -dihydronaphthalene (h) (0 mg, 0. mmol) in a mixture of NMP ( ml) and mesitylene ( ml). Compound nh was isolated by column chromatography as a white solid (0 mg, %). M.p.. o C H NMR (00 MHz, CDCl ): δ =.-. (m, H),.-. (m, H),. (s, H),. (t, J =. Hz, H),. (td, J =.0,. Hz, H); NMR (00 MHz, CDCl ): d = -., -., -. ppm; C NMR (CDCl, 00 MHz): δ =.-.0 (m, IC),.-. (m, IC),.- (m, C),.-. (m, C),.-.0 (m, C),.,, (q, J =. Hz, C),.,.,.00,.,. (q, J =. Hz, C),. (m, IC),.,. (t, J =. Hz, C) ppm; IR: v = 0,,,,,, 0,,,, 0 cm - ; S
14 MS (EI, 0 ev) m/z (%): (00) [M+], (), (), (), (), 0 (0). EI-HRMS m/z calcd. for C H :.0, found:.0. N -cycloheptenyl--nitrobenzene (ab) Compound ab was prepared following the general method from potassium -nitrobenzoate (a) ( mg, 0. mmol) and -bromocyclohept--ene (b) ( mg, ul, 0. mmol) in a mixture of NMP ( ml) and mesitylene ( ml). Compound ab was isolated by column chromatography as a yellow liquid (0 mg, %). H NMR (00 MHz, CDCl ): δ =. (dd, J =.,. HZ, H),.-. (m, H),.-. (m, H),. (dd, J =.,. Hz, H),. (t, J =. Hz, H),.-. (m, H),.0-. (m, H),.-. (m, H),.-. (m, H); C NMR (CDCl, 00 MHz): δ =.,.,.,.,., 0.,.,.,.0,.,.0,.,. ppm; IR: v =, 0,, 0,,, 0,,, cm - ; MS (EI, 0 ev) m/z (%): () [M+], (00), (0), 0 (), (), (). EI-HRMS m/z calcd. for C H N :.0, found:.. N -(-methylpent--en--yl)--nitrobenzene (ac) Compound ac was prepared following the general method from potassium -nitrobenzoate (a) ( mg, 0. mmol) and -bromo--methylpent--ene (c) ( mg, 0uL, 0. mmol) in a mixture of NMP ( ml) and mesitylene ( ml). Compound ac was isolated by column chromatography as a yellow liquid ( mg, %). S
15 H NMR (00 MHz, CDCl ): δ =. (d, J =.0 Hz, H),.-. (m, H),.-. (m, H),. (d, J =.0 Hz, H),. (s, H),.0 (s, H),. (d, J =.0 Hz, H),.-. (m, H), 0. (s, H), 0. (s, H); C NMR (CDCl, 00 MHz): δ =.0,.,.,.,.,.,.0,.,.,.,. (C) ppm; IR: v =,,,,,, 0, 0,, 0 cm - ; MS (EI, 0 ev) m/z (%): 0 () [M+], 0 (), (), 0 (), (00), (), (). EI-HRMS m/z calcd. for C H N : 0.0, found: 0.. N -(-methylbut--en--yl)--nitrobenzene (ad) Compound ad was prepared following the general method from potassium -nitrobenzoate (a) ( mg, 0. mmol) and -bromo--methylbut--ene (d) ( mg, 0uL, 0. mmol) in a mixture of NMP ( ml) and mesitylene ( ml). Compound ad was isolated by column chromatography as a yellow liquid ( mg, 0%). H NMR (00 MHz, CDCl ): δ =. (dd, J =.0,. Hz, H),. (td, J =.,. Hz, H),. (m, H),. (dd, J =.,. Hz, H),. (m, H),. (s, H),.0-. (m, H); C NMR (CDCl, 00 MHz): δ =., 0.,.,,.,.0,.,.,., 0.,. ppm; IR: v =,, 0,, 0,, 0,,, cm - ; MS (EI, 0 ev) m/z (%): () [M+], (), (00), 0 (), (0), (). EI-HRMS m/z calcd. for C H N :, found:. N S
16 -nitro--(-phenylvinyl)benzene (ae) Compound e was prepared following the general method from potassium -nitrobenzoate (a) ( mg, 0. mmol) and (-bromovinyl)benzene (e) (mg, 0. mmol) in a mixture of NMP ( ml) and mesitylene ( ml). Compound ae was isolated by column chromatography as a yellow liquid ( mg, %). H NMR (00 MHz, CDCl ): δ =. (d, J =.0 Hz, H),.-. (m, H),.-. (m, H),.-. (m, H),. (s, H),. (s, H); C NMR (CDCl, 00 MHz): δ =.,,.,.,.,.,.,. (C),.,.0 (C),.,. ppm; IR: v =,,,,,, 0, cm - ; MS (EI, 0 ev) m/z (%): () [M+], (00), 0 (), 0 (), (), 0 (), (). EI-HRMS m/z calcd. for C H N :.0, found:.0. N (E)--nitro--(-phenylprop--enyl)benzene (af) Compound af was prepared following the general method from potassium -nitrobenzoate (a) ( mg, 0. mmol) and (-bromoprop--enyl)benzene (e) (E:Z = :) (mg, 0. mmol) in a mixture of NMP ( ml) and mesitylene ( ml). Compound af was isolated by column chromatography as a yellow liquid ( mg, %) along with the expected % of the Z isomer. H NMR (00 MHz, CDCl ): δ =.0 (dd, J =.,. Hz, H),. (td, J =.,. Hz, H),.-. (m, H),. (dd, J =.,. Hz, H),.-.0 (m, H),. (q, J =. Hz, H),. (d, J =.0 Hz, H); C NMR (CDCl, 00 MHz): δ =., 0.,.,.,,, (C),. (C),.,.,.,.,. ppm; S
17 IR: v = 0,,,, 0,,,,,,, cm - ; MS (EI, 0 ev) m/z (%): () [M+], (00), (), (), 0 (), (). EI-HRMS m/z calcd. for C H N :.0, found:.0. N -(-nitrophenyl)-,-dihydronaphthalene (ag) Compound ag was prepared following the general method from potassium -nitrobenzoate (a) ( mg, 0. mmol) and -bromo-, -dihydronaphthalene (g) (0mg, 0. mmol) in a mixture of NMP ( ml) and mesitylene ( ml). Compound ag was isolated by column chromatography as a yellow liquid ( mg, %). H NMR (00 MHz, CDCl ): δ =.0 (d, J =.0 Hz, H),.-. (m, H),.-. (m, H),.-.0 (m, H),.0 (d, J =.0 Hz, H),. (t, J =. Hz, H),.0-. (m, H),.-. (m, H); C NMR (CDCl, 0 MHz): δ =.0,.,.,.,.,.,.,., 0,.,.0,.,.,.,.,. ppm; IR: v = 0,,,,, 0,, 0, cm - ; MS (EI, 0 ev) m/z (%): () [M+], (0), (), 0 (00), (), (0), (0). EI-HRMS m/z calcd. for C H N :, found:. N -(-nitrophenyl)-, -dihydronaphthalene (ah) Compound ah was prepared following the general method from potassium -nitrobenzoate (a) ( mg, 0. mmol) and -bromo-, -dihydronaphthalene (h) S
18 (0mg, 0. mmol) in a mixture of NMP ( ml) and mesitylene ( ml). Compound ah was isolated by column chromatography as a yellow liquid ( mg, %). H NMR (00 MHz, CDCl ): δ =.-. (m, H),.-. (m, H),.-. (m, H),.-. (m, H),.-. (m, H),. (s, H),.0-. (m, H),.-. (m, H); C NMR (CDCl, 00 MHz): δ =.,,.,.,.,., 0.,,.,.,.,.0,.,.,.,. ppm; IR: v = 0,, 0,,, 0,,,, cm - ; MS (EI, 0 ev) m/z (%): () [M+], (00), (), 0 (0), (), (). EI-HRMS m/z calcd. for C C H N :, found:. N -(-nitrophenyl)-,-dioxaspiro[.]dec--ene (ai) Compound ai was prepared following the general method from potassium -nitrobenzoate (a) ( mg, 0. mmol) and -bromo-, -dioxaspiro[.]dec--ene (i) (0mg, 0. mmol) in a mixture of NMP ( ml) and mesitylene ( ml). Compound ai was isolated by column chromatography as a yellow liquid ( mg, %). H NMR (00 MHz, CDCl ): δ =. (d, J =.0 Hz, H),.-. (m, H),.-. (m, H),. (d, J =.0 Hz, H),.-. (m, H),.0-.0 (m, H),.-. (m, H),. (t, J =. Hz, H); C NMR (CDCl, 00 MHz): δ =.,.,.,., 0.,.,.0,., 0.,.(C),.0,.,. ppm; IR: v =,,,,,,,, 00, 0,, cm - ; MS (EI, 0 ev) m/z (%): () [M+], (), (), (0), (00), (). S
19 EI-HRMS m/z calcd. for C H N :.00, found:.000. N -cyclohexenyl--fluoro--nitrobenzene (aj) Compound aj was prepared following the general method from potassium -nitrobenzoate (a) ( mg, 0. mmol) and (E)-(-bromovinyl)benzene (j) ( mg, 0. mmol) in a mixture of NMP ( ml) and mesitylene ( ml). Compound aj was isolated by column chromatography as a yellow liquid (0 mg, %). H NMR (00 MHz, CDCl ): δ =. (dd, J =.,. Hz, H),.-. (m, H),.-. (m, H),.-. (m, H),.-. (m, H),.-. (m, H),.0 (d, J =., H); C NMR (CDCl, 00 MHz): δ =.,.,.,,.,.(C),.,,.,.(C),.,. ppm; IR: v = 0, 0, 0, 0,,,,,,, cm - ; MS (EI, 0 ev) m/z (%): () [M+], 0 (), 0 (), (), (), (00), (). EI-HRMS m/z calcd. for C H N :.00, found:.0. References (). Spaggiari, A.; Vaccari, D.; Davoli, P.; Torre, G.; Prati,. J. rg. Chem. 00,,. (). Bigot, A.; Breuninger, D.; Breit, B. rg. Lett. 00, 0,. (). Voets, M.; Antes, I.; Scherer, C.; Müller-Vieira, U.; Biemel, K.; Marchais-berwinkler, S.; Hartmann, R. W. J. Med. Chem. 00,,. (). Das, J. P.; Roy, S. J. rg. Chem. 00,,. (). Renoll, M. W. J. Am. Chem. Soc.,,. (). Adam, W.; Richter, M. J. Synthesis,,. S
20 NMR spectra TAN00-H.ESP aa TAN00-c.esp aa S0
21 TANb-h.esp ba TANb-c.esp ba S
22 TAN-h.esp ca CH TANa-c.esp ca CH S
23 TANa-h.esp C H 0 da TANa-c.esp H C 0 da S
24 TAN0-h.esp CH 0 ea TAN0-c.esp ea CH S
25 TAN-h.esp H C 0 fa TAN-c.esp.. H C 0 fa S
26 TAN-h.esp CH H C ga TANb-c.esp CH H C ga S
27 TAN-h.esp CH ha TAN-c.esp CH.00.. ha S
28 TANb-h.esp ia TANb-c.esp ia S
29 TAN0a-h.esp S ja TAN0a-c.esp S. ja S
30 TAN-h.esp N CH 0 ka TAN-c.esp ka N CH TAN-H.ESP lh S0
31 TAN-C.ESP lh TAN0a-h.esp mh TAN0-c.esp mh S
32 TAN0a-f.esp mh Normalized Intensity TANa-h.esp nh S
33 TANa-c.esp nh TANa-f.esp nh Normalized Intensity S
34 TAN0a-c.esp ab TAN0a-h.esp ab S
35 TAN-H.ESP H C H C 0 CH ac SPEC.ESP H C H C 0 CH. ac TAN-h.esp CH - H C 0 CH ad S
36 TAN-C.ESP CH H C 0 CH ad TANA-H.ESP H C 0 ae S
37 TANa-c.esp H C 0 ae TAN-H.ESP H C - 0 af TAN-C.ESP H C - 0 af S
38 TANA-H.ESP ag TAN-C.ESP ag S
39 TANa-h.esp ah TANa-c.esp ah S
40 TAN-h.esp ai TAN-c.esp ai TANb-h.esp aj S0
41 TANb-c.esp aj S
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