Supporting Information

Supporting Information Direct Olefination of Alcohols with Sulfones by Using Heterogeneous Platinum Catalysts S. M. A. Hakim Siddiki, [a] Abeda Sultana Touchy, [b] Kenichi Kon, [b] [a, b] and Ken-ichi Shimizu* chem_201505109_sm_miscellaneous_information.pdf

Supporting Information Direct Olefination of Alcohols with Sulfones by Heterogeneous Platinum Catalysts S. M. A. Hakim Siddiki, a Abeda Sultana Touchy, b Kenichi Kon, b Ken-ichi Shimizu* a,b a Elements Strategy Initiative for Catalysts and Batteries, Kyoto University, Katsura, Kyoto 615-8520, Japan b Institute for Catalysis, Hokkaido University, N-21, W-10, Sapporo 001-0021, Japan *Corresponding author Ken-ichi Shimizu Institute for Catalysis, Hokkaido University, N-21, W-10, Sapporo 001-0021, Japan E-mail: kshimizu@cat.hokudai.ac.jp, Fax: +81-11-706-9163 NMR and GC/MS analysis 1 H and 13 C NMR spectra for olefins of Table-4 and Table-5 were assigned and reproduced to the corresponding literature. 1 H and 13 C NMR spectra were recorded using at ambient temperature on JEOL-ECX 600 operating at 600.17 and 150.92 MHz, respectively with tetramethylsilane as an internal standard. All chemical shifts (δ) are reported in ppm and coupling constants (J) in Hz. All chemical shifts are reported relative to tetramethylsilane and d-solvent peaks 77.00 ppm chloroform. Abbreviations used in the NMR experiments: s, singlet; d, doublet; t, triplet; q, quartet; m, multiplet. GC-MS spectra was taken by SHIMADZU QP2010. Vinyl-benzene: GC-MS m/e 104.065. 1-Methyl-4-vinyl-benzene : [1] 1 H NMR (600.17 MHz, CDCl 3, TMS): δ 7.28 (d, J = 8.22 Hz, 2H), 7.10 (d, J = 7.62 Hz, 2H), 6.80 (dd, J = 17.82, 10.98 Hz, 1H), 5.68 (d, J = 17.82 Hz, 1H), 5.16 (d, J = 11.04 Hz, 1H), 2.33 (s, 3H); 13 C NMR (150.92 MHz, CDCl 3 ) δ 137.57, 136.68, 134.75, 129.17 (C 2), 126.08 (C 2), 112.71, 21.17; GC-MS m/e 118.075. 1

1-Methoxy-4-vinyl-benzene : [1] MeO 1 H NMR (600.17 MHz, CDCl 3, TMS): δ 7.33 (d, J = 8.94 Hz, 2H), 7.10 (d, J = 8.94 Hz, 2H), 6.64 (dd, J = 17.52, 10.92 Hz, 1H), 5.61 (d, J = 17.60 Hz, 1H), 5.12 (d, J = 10.36 Hz, 1H), 3.78 (s, 3H); 13 C NMR (150.92 MHz, CDCl 3 ) δ 159.30, 136.17, 130.36, 127.23, 126.08 (C 2), 113.84, 111.50, 55.20; GC-MS m/e 134.075. 1-(tert-Butyl)-4-vinyl-benzene : [2] 1 H NMR (600.17 MHz, CDCl 3, TMS): δ 7.34 (s like, 4H), 6.68 (dd, J = 17.88, 10.98 Hz, 1H), 5.70 (d, J = 17.22 Hz, 1H), 5.18 (d, J = 10.98 Hz, 1H), 1.31 (s, 9H); 13 C NMR (150.92 MHz, CDCl 3 ) δ 150.82, 136.56, 134.80, 125.90, 125.40, 125.14, 125.09, 112.97, 34.54, 31.27 (C 3); GC-MS m/e 160.130. 1-Fluoro-4-vinyl-benzene: GC-MS m/e 122.055. F 1-Chloro-4-vinyl-benzene: GC-MS m/e 138.025. Cl 1-Trifluoromethyl-4-vinyl-benzene: GC-MS m/e 172.055. F 3 C 4-Vinyl-biphenyl : [1] Ph 1 H NMR (600.17 MHz, CDCl 3, TMS): δ 7.59-7.58 ( m, 2H), 7.56-7.54 (m, 2H), 7.48-7.46 (m, 2H), 7.43-7.40 (m, 2H), 7.34-7.31 (m, 1H), 6.74 (dd, J = 17.16, 10.98 Hz, 1H), 5.78(d, J = 17.16 Hz, 1H), 5.25 (d, J = 10.98 Hz, 1H); 13 C NMR (150.92 MHz, CDCl 3 ) δ 140.67, 140.53, 136.54, 136.36, 128.75(C 2), 127.28 (C 2), 127.19, 126.92 (C 2), 126.61(C 2), 113.87; GC-MS m/e 180.015. 2

1,2-Dimethoxy-4-vinyl-benzene : [1] MeO OMe 1 H NMR (600.17 MHz, CDCl 3, TMS): δ 6.96-6.92 ( m, 2H), 6.80 (d, J = 8.22 Hz, 1H), 6.64 (dd, J = 17.82, 11.04 Hz, 1H), 5.60 (d, J = 17.82 Hz, 1H), 5.14 (d, J = 11.04 Hz, 1H), 3.89 (s, 3H), 3.86 (s, 3H); 13 C NMR (150.92 MHz, CDCl 3 ) δ 148.84, 148.82, 136.35, 130.56, 119.32, 111.66, 110.86, 108.33, 55.75, 55.64; GC-MS m/e 164.085. 2-Vinylnapthalene : [1] 1 H NMR (600.17 MHz, CDCl 3, TMS): δ 7.72-7.69 (m, 3H), 7.66 (s, 1H), 7.57 (dd, J = 8.94, 2.04 Hz, 1H), 7.38-7.36 (m, 2H), 6.80 (dd, J = 17.62, 10.98 Hz, 1H), 5.78(d, J = 17.62 Hz, 1H), 5.25 (d, J = 10.98 Hz, 1H); 13 C NMR (150.92 MHz, CDCl 3 ) δ 136.86, 134.94, 133.50, 133.10, 128.09, 127.98, 127.60, 126.35, 126.15, 125.83, 123.06, 114.07; GC-MS m/e 154.075. 1-Vinylnapthalene : [1] 1 H NMR (600.17 MHz, CDCl 3, TMS): δ 8.07 (d, J = 7.56 Hz, 1H), 7.80 (d, J = 8.22 Hz, 1H), 7.73 (d, J = 8.22 Hz, 1H), 7.58 (d, J = 7.56 Hz, 1H), 7.48-7.40 (m, 4H), 5.75 (dd, J = 17.62, 1.38 Hz, 1H), 5.43 (dd, J = 10.68, 1.38 Hz, 1H); 13 C NMR (150.92 MHz, CDCl 3 ) δ 135.50, 134.28, 133.50, 131.02, 128.44, 128.03, 125.98, 125.67, 125.56, 123.67, 123.54, 117.01; GC-MS m/e 154.075. 2-Vinyl-furan: GC-MS m/e 94.045. O 2-Vinyl-thiophene: GC-MS m/e 110.015. S 3

2-Vinylpyridine : [3] N 1 H NMR (600.17 MHz, CDCl 3, TMS): δ 8.57 (d like s, 1H), 7.64 (t, J = 7.56 Hz, 1H), 7.34 (d, J = 7.56 Hz, 1H), 7.15 (m, 1H), 6.82 (dd, J = 17.88, 10.98 Hz, 1H), 6.20 (d, J = 17.88 Hz, 1H), 5.48 (d, J = 10.98 Hz, 1H); 13 C NMR (150.92 MHz, CDCl 3 ) δ 155.72, 149.49, 136.91, 136.44, 122.41, 121.18, 118.16 ; GC-MS m/e 105.045. 5-Vinyl-benzo[1,3]dioxole: [4] O O 1 H NMR (600.17 MHz, CDCl 3, TMS): δ 6.95 (s, 1H), 6.80 (dd, J = 8.37, 1.38 Hz, 1H), 6.75 (d, J = 7.65 Hz, 1H), 6.60 (dd, J = 17.24, 10.98 Hz, 1H), 5.94 (s, 2H), 5.56 (d, J = 17.24 Hz, 1H), 5.12 (d, J = 10.98 Hz, 1H); 13 C NMR (150.92 MHz, CDCl 3 ) δ 147.96, 147.32, 136.31, 132.08, 120.98, 111.93, 108.15, 105.35, 101.01; GC-MS m/e 148.065. Non-1-ene: GC-MS m/e 126.145. n-c 7 H 15 Vinyl-cyclohexane: GC-MS m/e 110.105. 4-Methyl-penta-1,3-diene:GC-MS m/e 82.075. Buta-1,3-dienyl-benzene : [5] 1 H NMR (600.17 MHz, CDCl 3, TMS): δ 7.39 (d, J = 8.22 Hz, 2H), 7.31-7.28 ( m, 2H), 7.22-7.20 (m, 1H), 6.80 (dd, J = 18.48, 10.98 Hz, 1H), 6.51(dd, J = 17.16, 9.60 Hz, 2H), 5.32 (d, J = 17.16 Hz, 1H), 5.16 (d, J = 9.60 Hz, 1H); 13 C NMR (150.92 MHz, CDCl 3 ) δ 137.13, 137.05, 132.80, 129.56, 128.56 (C 2), 127.58, 126.38 (C 2), 117.58; GC-MS m/e 130.085. 4

Isopropenyl-benzene : [6] 1 H NMR (600.17 MHz, CDCl 3, TMS): δ 7.47-7.45 (m, 2H), 7.34-7.31 (m, 2H)), 7.27-7.25 (m, 1H), 5.36 (s, 1H), 5.08 (s, 1H), 2.15 (s, 3H); 13 C NMR (150.92 MHz, CDCl 3 ) δ 143.24, 141.17, 128.19 (C 2), 127.37, 125.45 (C 2), 112.38, 21.80; GC-MS m/e 118.075 1-Isopropenyl-4-methyl-benzene : [6] 1 H NMR (600.17 MHz, CDCl 3, TMS): δ 7.37 (d, J = 8.22 Hz, 2H), 7.13 (d, J = 8.22 Hz, 2H), 5.33 (s, 1H), 5.02 (s, 1H), 2.33 (s, 3H), 2.13 (s, 3H); 13 C NMR (150.92 MHz, CDCl 3 ) δ 143.05, 138.31, 137.12, 128.88 (C 2), 125.33 (C 2), 111.53, 21.83, 21.04; GC-MS m/e 132.015. 1-Isopropenyl-4-methoxy-benzene: [7] MeO 1 H NMR (600.17 MHz, CDCl 3, TMS): δ 7.41 (d, J = 8.61 Hz, 2H), 6.85 (d, J = 8.61 Hz, 2H), 5.28 (s, 1H), 4.98 (s, 1H), 3.80 (s, 3H), 2.12 (s, 3H); 13 C NMR (150.92 MHz, CDCl 3 ) δ 159.02, 142.51, 133.70, 126.56 (C 2), 113.50 (C 2), 110.62, 55.24, 21.88; GC-MS m/e 148.165. 2-Isopropenyl-naphthalene : [8] 1 H NMR (600.17 MHz, CDCl 3, TMS): δ 7.84-7.77 (m, 4H), 7.66 (dd, J = 8.64, 2.04 Hz, 1H), 7.46-7.43 (m, 2H), 5.53 (s, 1H), 5.19 (s, 1H), 2.26 (s, 3H); 13 C NMR (150.92 MHz, CDCl 3 ) δ 142.96, 138.30, 133.35, 132.76, 128.21, 127.66, 127.47, 126.08, 125.79, 124.23, 123.86, 113.00, 21.86; GC-MS m/e 168.115. 1,1-Diphenyl-ethene : [9] 5

1 H NMR (600.17 MHz, CDCl 3, TMS): δ 7.33-7.31 (m, 10H), 5.45 (s, 2H); 13 C NMR (150.92 MHz, CDCl 3 ) δ 150.01, 141.44 (C 2), 128.24 (C 4), 128.13 (C 4), 127.68 (C 2), 114.26; GC-MS m/e 180.105. Propenyl-benzene: GC-MS m/e 118.075. 1-Methyl-4-propenyl-benzene: [1] 1 H NMR (600.17 MHz, CDCl 3, TMS): δ 7.21 (d, J = 8.22 Hz, 2H), 7.08 (d, J = 7.56 Hz, 2H), 6.35 (d, J = 15.78 Hz, 1H), 6.19-6.17 (m, 1H), 2.31 (s, 3H), 1.86 (d, J = 6.90 Hz, 3H); 13 C NMR (150.92 MHz, CDCl 3 ): δ 136.35, 135.11, 130.80, 129.13 (C 2), 125.67 (C 2), 124.58, 21.10, 18.44; GC-MS m/e 132.095. 1-Methoxy-4-propenyl-benzene: [1] MeO 1 H NMR (600.17 MHz, CDCl 3, TMS): δ 7.24 (d, J = 8.28 Hz, 2H), 6.81 (d, J = 8.28 Hz, 2H), 6.32 (d, J = 15.24 Hz, 1H), 6.09-6.07 (m, 1H), 3.77 (s, 3H), 1.84 (d, J = 6.90 Hz, 3H); 13 C NMR (150.92 MHz, CDCl 3 ): δ 158.51, 130.76, 130.28, 126.83 (C 2), 123.45, 113.85 (C 2), 55.22, 18.40; GC-MS m/e 148.085. 1-tert-Butyl-4-propenyl-benzene: [10] 1 H NMR (600.17 MHz, CDCl 3, TMS): δ 7.31 (d like, 2H), 7.27 (d like, 2H), 6.37 (d, J = 15.84 Hz, 1H), 6.19-6.18 (m, 1H), 1.86 (d, J = 4.80 Hz, 3H), 1.30 (s, 9H); 13 C NMR (150.92 MHz, CDCl 3 ): δ 149.65, 135.16, 130.68, 125.49 (C 2), 125.35 (C 2), 124.85, 34.45, 31.30 (C 3), 18.48; GC-MS m/e 174.145. 1-Chloro-4-propenyl-benzene:GC-MS m/e 152.035. Cl 6

4-Propenyl-biphenyl: [11] Ph 1 H NMR (600.17 MHz, CDCl 3, TMS): δ 7.56 (d, J = 6.90 Hz, 2H), 7.50 (d, J = 8.28 Hz, 2H), 7.24-7.36 (m, 4H), 7.32-7.28 (m, 1H), 6.41 (d, J = 15.78 Hz, 1H), 6.27-6.23 (m, 1H), 1.87 (d, J = 6.84 Hz, 3H); 13 C NMR (150.92 MHz, CDCl 3 ): δ 140.79, 139.40, 136.93, 130.54, 128.70 (C 2), 127.12 (C 2), 127.07, 126.82 (C 2), 126.18 (C 2), 125.82, 18.54; GC-MS m/e 194.105. 1,2-Dimethoxy-4-propenyl-benzene:GC-MS m/e 178.095. MeO OMe 2-Propenyl-naphthalene: [1] 1 H NMR (600.17 MHz, CDCl 3, TMS): δ 7.76-7.73 (m, 3H), 7.63 (s, 1H), 7.54 (dd, J = 8.64, 2.04 Hz, 1H), 7.43-7.39 (m, 2H), 6.54 (d, J = 15.78 Hz, 1H), 6.37-6.34 (m, 1H), 1.91 (d, J = 4.80 Hz, 3H); 13 C NMR (150.92 MHz, CDCl 3 ): δ, 135.34, 133.68, 132.58, 131.11, 128.01, 127.79, 127.59, 126.15, 126.07, 125.38, 125.15, 123.46, 18.61; GC-MS m/e 168.095. 2-Propenyl-thiophene: [12] S 1 H NMR (600.17 MHz, CDCl 3, TMS): δ 7.06 (d, J = 5.46 Hz, 1H), 6.91 (t, J = 4.80 Hz, 1H), 6.84 (d, J = 2.76 Hz, 1H), 6.51 (d, J = 15.12 Hz, 1H), 6.08-6.05 (m, 1H), 1.84 (d, J = 6.90 Hz, 3H); 13 C NMR (150.92 MHz, CDCl 3 ): δ 143.05, 127.11, 125.70, 124.22, 123.91, 122.91, 18.24 ; GC-MS m/e 124.035. 3-Propenyl-pyridine: [13] N 1 H NMR (600.17 MHz, CDCl 3, TMS): δ 8.55 (s, 1H), 8.42 (s, 1H), 7.64 (d, J = 7.56 Hz, 1H), 7.22-7.20 (m, 1H), 6.38 (d, J = 17.16 Hz, 1H), 6.34-6.39 (m, 1H), 1.91 (d, J = 7.56 Hz, 3H); 13 C NMR (150.92 MHz, CDCl 3 ): δ 147.83, 147.79, 133.40, 132.27, 128.24, 127.50, 123.37, 18.62 ; 7

GC-MS m/e 119.075. 5-Propenyl-benzo[1,3]dioxole: [14] O O 1 H NMR (600.17 MHz, CDCl 3, TMS): δ 6.87 (s, 1H), 6.72 (s, 2H), 6.29 (d, J = 15.84 Hz, 1H), 6.07-6.03 (m, 1H), 5.91 (s, 2H), 1.84 (d, J = 6.18 Hz, 3H), 13 C NMR (150.92 MHz, CDCl 3 ): δ 147.86, 146.44, 132.44, 130.49, 123.87, 120.02, 108.15, 105.27, 100.85, 18.30; GC-MS m/e 162.065. Penta-1,3-dienyl-benzene: [15] 1 H NMR (600.17 MHz, CDCl 3, TMS): δ 7.40 (d, J = 6.90 Hz, 2H), 7.37-7.32 (m, 2H), 7.26-7.23 (m, 1H), 6.80-6.78 (m, 1H), 6.46 (d, J = 15.06 Hz, 1H), 6.28-6.26 (m, 1H), 5.89-5.86 (m, 1H), 1.86 (d, J = 6.18 Hz, 3H); 13 C NMR (150.92 MHz, CDCl 3 ): δ 137.60, 131.82, 130.25, 129.68, 129.28, 128.48 (C 2), 127.01, 126.07 (C 2), 18.32; GC-MS m/e 144.095. (E)-1,2-Diphenylethene [16] Ph 1 H NMR (600.17 MHz, CDCl 3, TMS): δ 7.50 (d, J = 7.56 Hz, 4H), 7.34 (t, J = 7.62 Hz, 4H), 7.24 (t, J = 7.56 Hz, 2H), 7.09 (s, 2H); 13 C NMR (150.92 MHz, CDCl 3 ): δ 137.26 (C 2), 128.64 (C 4), 128.41 (C 2), 128.29, 127.58 (C 4), 126.47 ; GC-MS m/e 180.095. 1-Methyl-4-styryl-benzene: [1] Ph 1 H NMR (600.17 MHz, CDCl 3, TMS): δ 7.49 (d, J = 7.56 Hz, 2H), 7.40 (d, J = 8.28 Hz, 2H), 7.34 (t, J = 7.56 Hz, 2H), 7.23 (t, J = 7.56 Hz, 1H), 7.16 (d, J = 8.22 Hz, 2H), 7.06 (d, J = 4.80 Hz, 2H), 2.35 (s, 3H); 13 C NMR (150.92 MHz, CDCl 3 ): δ 137.49, 137.47, 134.50, 129.37 (C 2), 128.63 (C 2), 128.57, 127.65, 127.37, 126.40 (C 2), 126.37 (C 2), 21.24; GC-MS m/e 194.105. 8

1-Methoxy-4-styryl-benzene: [1] Ph MeO 1 H NMR (600.17 MHz, CDCl 3, TMS): δ 7.48 (d, J = 7.56 Hz, 2H), 7.44 (d, J = 8.22 Hz, 2H), 7.33 (t, J = 7.56 Hz, 2H), 7.22 (t, J = 7.56 Hz, 1H), 7.06 (d, J = 15.78 Hz, 1H), 6.97 (d, J = 15.78 Hz, 1H), 6.89 (d, J = 8.22 Hz, 2H), 3.82 (s, 3H); 13 C NMR (150.92 MHz, CDCl 3 ): δ 159.30, 137.64, 130.14, 128.62 (C 2), 128.20, 127.69 (C 2), 127.20, 126.61, 126.23 (C 2), 114.13 (C 2), 55.32; GC-MS m/e 210.105. 1-tert-Butyl-4-styryl-benzene: [16] Ph 1 H NMR (600.17 MHz, CDCl 3, TMS): δ 7.49 (d, J = 7.56 Hz, 2H), 7.45 (d, J = 8.22 Hz, 2H), 7.36 (d, J = 8.22 Hz, 2H), 7.34 (t, J = 7.56 Hz, 2H), 7.23 (t, J = 7.56 Hz, 1H), 7.08 (d, J = 5.52 Hz, 2H), 1.31 (s, 9H); 13 C NMR (150.92 MHz, CDCl 3 ): δ 150.75, 137.50, 134.52, 128.63 (C 2), 128.46, 127.89, 127.39, 126.39 (C 2), 126.22 (C 2), 125.60 (C 2), 34.60, 31.27; GC-MS m/e 236.160. 1-Fluoro-4-styryl-benzene: [16] Ph F 1 H NMR (600.17 MHz, CDCl 3, TMS): δ 750-7.46 (m, 4H), 7.35 (t, J = 7.56 Hz, 2H), 7.26 (t, J = 7.56 Hz, 1H), 7.08-7.02 (m, 4H); 13 C NMR (150.92 MHz, CDCl 3 ): δ 162.30 (d, J = 247.59 Hz, 4-F-C ), 137.13, 133.46, 128.69, 128.44, 127.95 (d, J = 8.06 Hz, meta to 4-F, C 2 ), 127.65, 127.44, 126.41, 115.60 (d, J = 8.06 Hz, ortho to 4-F, C 2 ); GC-MS m/e 198.085. 1-Chloro-4-styryl-benzene: [1] Ph Cl 1 H NMR (600.17 MHz, CDCl 3, TMS): δ 7.49 (d, J = 7.56 Hz, 2H), 7.42 (d, J = 8.22 Hz, 2H), 7.35 (t, J = 7.56 Hz, 2H), 7.31 (d, J = 8.22 Hz, 2H), 7.26 (t, J = 7.56 Hz, 1H), 7.06 (d, J = 5.46 Hz, 2H); 13 C NMR (150.92 MHz, CDCl 3 ): δ 136.93, 135.79, 133.13, 129.26, 128.81 (C 2), 128.71 (C 2), 127.84, 127.63 (C 2), 127.31, 126.52 (C 2); GC-MS m/e 214.055. 9

4-Styryl-biphenyl: [1] Ph Ph 1 H NMR (600.17 MHz, CDCl 3, TMS): δ 7.62-7.58 (m, 3H), 7.45 (d, J = 8.22Hz, 2H), 7.41 (t, J = 7.56 Hz, 2H), 7.34-7.29 (m, 4H), 7.24 (t, J = 7.56 Hz, 2H), 7.21 (m, 1H) 6.62 (s, 2H); 13 C NMR (150.92 MHz, CDCl 3 ): δ 140.67, 139.71, 137.32, 136.21, 130.39, 129.78, 129.32 (C 2), 128.86 (C 2), 128.74 (C 2), 128.26 (C 2), 127.25, 127.14, 126.87 (C 2), 126.80 (C 2) ; GC-MS m/e 256.135. 1,2-Dimethoxy-4-styryl-benzene: [17] Ph MeO OMe 1 H NMR (600.17 MHz, CDCl 3, TMS): δ 7.49 (d, J = 7.56 Hz, 2H), 7.34 (t, J = 7.56 Hz, 2H), 7.23 (t, J = 7.56 Hz, 1H), 7.06-7.03 (m, 3H), 6.97 (d, J = 15.84 Hz, 1H), 6.84 (d, J = 8.28 Hz, 1H), 3.93 (s, 3H), 3.88 (s, 3H); 13 C NMR (150.92 MHz, CDCl 3 ): δ 149.02, 148.83, 137.42, 130.34, 128.59 (C 2), 128.37, 127.21, 126.71, 126.19 (C 2), 119.81, 111.10, 108.62, 55.84, 55.71; GC-MS m/e 240.115. 2-Styryl-naphthalene: [18] Ph 1 H NMR (600.17 MHz, CDCl 3, TMS): δ 7.85-7.80 (m, 4H)), 7.74 (d, J = 8.22 Hz, 1H), 7.56 (d, J = 8.22 Hz, 2H), 7.48-7.43 (m, 2H), 7.37 (t, J = 6.18 Hz, 2H), 7.29-7.23 (m, 3H); 13 C NMR (150.92 MHz, CDCl 3 ): δ 137.31, 134.78, 133.67, 133.01, 128.98, 128.73, 128.71 (C 2), 128.28, 127.97, 127.67 (C 2), 126.62, 126.52 (C 2), 126.31, 125.88, 123.47 ; GC-MS m/e 230.110. 1-Styryl-naphthalene: [1] Ph 1 H NMR (600.17 MHz, CDCl 3, TMS): δ 8.20 (d, J = 8.22 Hz, 1H), 7.88-7.84 (m, 2H), 7.78 (d, J = 8.22 Hz, 1H), 7.72 (d, J = 7.56 Hz, 1H), 7.58 (d, J = 7.56 Hz, 2H), 7.53-7.46 (m, 3H), 7.38 ( t, J = 7.56 Hz, 2H), 7.28 ( t, J = 7.56 Hz, 1H), 7.13 (d, J = 15.78 Hz, 1H); 13 C NMR (150.92 MHz, 10

CDCl 3 ): δ 137.60, 135.01, 133.72, 131.75, 131.39, 128.73 (C 2), 128.59, 128.02, 127.76, 126.67 (C 2), 126.07, 125.81, 125.67, 125.67, 123.76, 123.61; GC-MS m/e 230.110. 2-Styryl-furan: [19] O Ph 1 H NMR (600.17 MHz, CDCl 3, TMS): 7.46 (d, J = 7.56 Hz, 2H), 7.40 (d, J = 1.32 Hz, 1H), 7.33 (t, J = 7.56 Hz, 2H), 7.23 (t, J = 7.56 Hz, 1H), 7.03 (d, J = 16.50 Hz, 1H), 6.89 (d, J = 16.50 Hz, 1H), 6.41 (d, J = 4.8 Hz, 1H), 6.35 (d, J = 4.8 Hz, 1H); 13 C NMR (150.92 MHz, CDCl 3 ): δ 153.25, 142.10, 137.02, 128.65 (C 2), 127.54, 127.12, 126.30 (C 2), 116.52, 111.61, 108.52; GC-MS m/e 170.075. 2-Styryl-thiophene: [16] S Ph 1 H NMR (600.17 MHz, CDCl 3, TMS): δ 7.43 (d, J = 7.56 Hz, 2H), 7.32 (t, J = 7.56 Hz, 2H), 7.22 (t, J = 7.56 Hz, 1H), 7.20 (d, J = 16.50 Hz, 1H), 7.15 (d, J = 4.80 Hz, 1H), 7.04 (d, J = 3.48 Hz, 1H), 6.97 (t, J = 3.48 Hz, 1H), 6.91 (d, J = 18.15 Hz, 1H); 13 C NMR (150.92 MHz, CDCl 3 ): δ 142.83, 136.91, 128.65 (C 2), 128.30, 127.54 (C 2), 126.26 (C 2), 126.05, 124.28, 121.74; GC-MS m/e 186.050. 3-Styryl-pyridine: [20] Ph N 1 H NMR (600.17 MHz, CDCl 3, TMS): δ 8.72 (s, 1H), 8.48 (d, J = 2.04 Hz, 1H), 7.83 (t like, 1H), 7.53 (d, J = 7.56 Hz, 2H), 7.38 (t, J = 7.56 Hz, 2H), 7.31-7.25 (m, 2H), 7.16 (d, J = 16.50 Hz, 1H), 7.07 (d, J = 16.60 Hz, 1H); 13 C NMR (150.92 MHz, CDCl 3 ) δ 148.56 (C 2), 136.51, 132.88, 132.62, 130.81, 128.78 (C 2), 128.20, 126.65 (C 2), 124.89, 123.48; GC-MS m/e 181.080. 5-Styryl-benzo[1,3]dioxole: [21] O Ph O 1 H NMR (600.17 MHz, CDCl 3, TMS): δ 7.47 (d, J = 7.56 Hz, 2H), 7.33 (t, J = 7.56 Hz, 2H), 7.23 11

(t, J = 7.56 Hz, 1H), 7.06 (d, J = 1.38 Hz, 1H), 7.01 (d, J = 15.84 Hz, 1H), 6.93-6.91 (m, 2H ), 6.79 (d, J = 7.56 Hz, 1H), 5.95 (s, 2H); 13 C NMR (150.92 MHz, CDCl 3 ): δ 148.10, 147.27, 137.35, 131.82, 128.62 (C 2), 128.29, 127.32, 126.95, 126.27 (C 2), 121.44, 108.37, 105.49, 101.09; GC-MS m/e 224.080. (1E,3E)-1,4-Diphenylbuta-1,3-diene: [1] Ph 1 H NMR (600.17 MHz, CDCl 3, TMS): δ 7.43 (d, J = 7.56 Hz, 4H), 7.32 (t, J = 7.56 Hz, 4H), 7.22 (t, J = 7.56 Hz, 2H), 6.94 (dd, J = 11.70, 2.76 Hz, 2H), 6.66 (dd, J = 11.70, 2.76 Hz, 2H); 13 C NMR (150.92 MHz, CDCl 3 ): δ 137.30 (C 2), 132.78 (C 2), 129.21 (C 2), 128.63 (C 4), 127.53 (C 2), 126.34 (C 4); GC-MS m/e 206.110. (2-Cyclohexyl-vinyl)-benzene: [22] Ph 1 H NMR (600.17 MHz, CDCl 3, TMS): δ 7.34-7.26 (m, 3H), 7.18-7.15 (m, 3H), 5.26 (t, J = 7.56 Hz, 1H), 3.34 (d, J = 6.84 Hz, 2H), 2.24 ( (d, J = 5.28 Hz, 2H), 2.11 (d, J = 5.28 Hz, 2H), 1.81-1.67 (m, 1H), 1.59-1.54 (m, 3H), 1.32-1.16 (m, 1H); 13 C NMR (150.92 MHz, CDCl 3 ): δ 141.95, 140.57, 128.32 (C 2), 128.30 (C 2), 125.63, 119.72, 37.17, 33.38, 28.73, 28.61, 27.85, 26.91; GC-MS m/e 186.145. Non-1-enyl-benzene: [23] C 6 H 13 Ph 1 H NMR (600.17 MHz, CDCl 3, TMS): δ 7.33-7.16 (m, 3H), 7.18-7.15 (m, 3H), 5.51 (m, 1H), 3.32 (d, J = 6.18 Hz, 2H), 2.01 (d, J = 6.18 Hz, 2H), 1.28-1.25 (m, 8H), 0.89-0.86 (t, J = 6.18 Hz, 3H); 13 C NMR (150.92 MHz, CDCl 3 ): δ 132.27, 128.75, 128.57 (C 2), 128.41(C 2), 125.99, 125.93, 39.17, 32.63, 31.84, 29.55, 28.97, 22.75, 14.20; GC-MS m/e 202.175. 5-Phenyl-pent-4-enylamine: GC-MS m/e 161.125. H 2 N Ph 12

Ethyl-benzene: GC-MS m/e 106.075. 1-Ethyl-4-methoxy-benzene: GC-MS m/e 136.085. MeO 4-Ethyl-biphenyl: GC-MS m/e 182.105. Ph 4-Ethyl-1,2-dimethoxy-benzene: GC-MS m/e 166.095. MeO OMe 2-Ethyl-naphthalene: GC-MS m/e 156.095. 3-Ethyl-pyridine: GC-MS m/e 107.075. N Propyl-benzene: GC-MS m/e 120.095. 1,2-Diphenylethane: GC-MS m/e 182.105. Ph 13

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