Supporting Information
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- Ῥαχήλ Αλεξανδρίδης
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1 Supporting Information Wiley-VCH Weinheim, Germany Copper-Catalyzed Coupling of Oxime Acetates with Sodium Sulfinates: An Efficient Synthesis of Sulfone Derivatives** Xiaodong Tang, Liangbin Huang, Yanli Xu, Jidan Yang, Wanqing Wu, and Huanfeng Jiang* ange_ _sm_miscellaneous_information.pdf
2 Supporting Information Table of Contents General Information...[1] Typical Procedure for the Preparation of Oxime Acetates.....[1] Experimental Section for products 3 and 4 [1] Characterization Data for All Products...[1] A single crystal of product 3ta....[7] References [7] NMR Spectra for All Compounds [8]
3 General Information 1 H and 13 C NMR spectra were recorded on BRUKER DRX-400 spectrometer using CDCl 3 as solvent and TMS as an internal standard. Gas chromatograph mass spectra were obtained with a SHIMADZU model GCMS-QP5000 spectrometer. High-resolution mass spectra (ESI) were obtained with a LCMS-IT-TOF mass spectrometer. Unless otherwise stated, all reagents and solvents were purchased from commercial suppliers and used without further purification. Oxime acetates were synthesized according to the literature procedure. Typical Procedure for the Preparation of Oxime Acetates The mixture of ketoxime (3.0 mmol) and acetic anhydride (6.0 mmol) was stirred at 105 o C for 3 h. The reaction mixture was cooled to room temperature, diluted with EtOAc (25 ml) and washed with H 2 O (20 ml) and brine (10 ml). The organic layers were dried over anhydrous Na 2 SO 4 and evaporated in vacuum. The residue was purified by column chromatography on silica gel to afford the oxime acetates 1 with hexanes/ethyl acetate as the eluent. Experimental Section for products 3 and 4 General procedure for products 3: oxime acetates (0.5 mmol), sodium sulfinates (0.5 mmol), Cu(OAc) 2 (10 mol %), in DMSO (2 ml) were added to a 25 ml Schlenk tube with magnetic stirrer bar. The mixture was stirred at 100 C (oil bath temperature) for 6 h under N 2. After the reaction was finished (monitored by TLC), the mixture was cooled to room temperature and quenched with aqueous MgSO 4 and the solvent was removed under vacuum. The crude product was purified by flash column chromatography (EtOAc/hexanes) on silica gel. General procedure for products 4: oxime acetates (0.5 mmol), sodium sulfinates (0.5 mmol), Cu(OAc) 2 (10 mol %), in DMSO (2 ml) were added to a 25 ml Schlenk tube with magnetic stirrer bar. The mixture was stirred at 100 C (oil bath temperature) for 6 h under N 2. After the reaction was finished (monitored by TLC), the mixture was cooled to room temperature and quenched with aqueous MgSO 4 and the solvent was removed under vacuum. Then, the residue was stirred with silica gel in methylene dichloride at room temperature overnight. The resulting mixture was filtered and concentrated, and then the crude product was purified by column chromatography on silica gel using petroleum ether/etoac as eluent to provide the pure target product. Characterization data for all products NH 2 Ts (Z)-1-phenyl-2-tosylethenamine (3aa) 1 H NMR (400 MHz, DMSO) δ 7.84 (d, J = 8.2 Hz, 2H), 7.55 (d, J = 5.7 Hz, 2H), (m, 3H), 7.37 (d, J = 8.1 Hz, 2H), 7.11 (s, 2H), 5.15 (s, 1H), 2.36 (s,3h). 13 C NMR (100 MHz, DMSO) δ 156.2, 142.5, 142.2, 136.0, 130.6, , 128.6, 126.7, 125.5, 89.7, IR (KBr) ν (cm -1 ) 3459, 3360, 2925, 1622, 1286, 1134, 697. MS (EI, 70 ev) m/z (%): 273 (M+), 209, 193, 104, 91, 65. HRMS-ESI (m/z): calcd for C 15 H 15 NSO 2, [M+H]+ : ; found, (Z)-1-(o-tolyl)-2-tosylethenamine (3ja) 1 H NMR (400 MHz, CDCl 3 ) δ 7.84 (d, J = 8.2 Hz, 2H), 7.30 (d, J = 8.1 Hz, 2H), (m, 1H), (m, 3H), 4.78 (s, 1H), 2.43 (s, 3H), 2.29 (s, 3H). 13 C NMR (100 MHz, CDCl 3 ) δ 156.4, 143.0, 141.7, 137.2, 135.1, 130.7, , 129.5, 127.8, 126.0, 93.5, 21.5, IR (KBr) ν (cm -1 ) 3449, 3346, 1615, 1386, 1289,1131, 864. MS (EI, 70 ev) m/z (%): 387 (M+), 148, 132, 115, 91, 77. HRMS-ESI (m/z): calcd for C 16 H 17 NSO 2, [M+Na]+ : ; found,
4 (Z)-1-(2-chlorophenyl)-2-tosylethenamine (3ka) 1 H NMR (400 MHz, CDCl3) δ 7.85 (d, J = 7.8 Hz, 2H), (m, 6H), 4.85 (s, 1H), 2.42 (s, 3H). 13C NMR (101 MHz, CDCl3) δ 153.9, 143.2, 141.3, 136.1, 131.6, 130.8, 130.2, 129.8, 129.5, 127.1, 126.1, 94.6, IR (KBr) ν (cm-1) 3449, 3347, 1617, 1133, 862. MS (EI, 70 ev) m/z (%): 307 (M+), 272, 207, 133, 89, 77. HRMS-ESI (m/z): calcd for C15H14ClNSO2, [M+Na]+ : ; found, (Z)-1-(2-bromophenyl)-2-tosylethenamine (3la) 1 H NMR (400 MHz, CDCl3) δ 7.74 (d, J = 8.2 Hz, 2H), 7.42 (t, J = 7.7 Hz, 1H), (m, 5H), 4.66 (s, 1H), 2.32 (s, 3H). 13C NMR (100 MHz, CDCl3) δ 155.3, 143.2, 141.2, 138.1, 133.3, 131.0, 129.8, 129.6, 127.6, 126.1, 120.8, 94.1, IR (KBr) ν (cm-1) 3449, 3346, 1618, 1131, 832, 684. MS (EI, 70 ev) m/z (%): 353 (M+), 272, 193, 133, 117, 89, 65. HRMS-ESI (m/z): calcd for C15H14BrNSO2, [M+Na]+ : ; found, Ts H2N (Z)-1-(naphthalen-1-yl)-2-tosylethenamine (3ta) 1 H NMR (400 MHz, CDCl3) δ (m, 1H), (m, 4H), (m, 4H), 7.32 (d, J = 8.1 Hz, 2H), 4.97 (s, 1H), 2.44 (s, 3H). 13C NMR (100 MHz, CDCl3) δ 155.6, 143.1, 141.7, 135.0, 133.6, 130.1, 130.1, 129.7, , 127.0, 126.4, 126.0, 125.7, 125.0, 124.8, 94. 5, IR (KBr) ν (cm-1) 3741, 1707, 1514, 1292, 778. MS (EI, 70 ev) m/z (%): 323 (M+), 258, 207, 168, 141, 91, 65. HRMS-ESI (m/z): calcd for C19H17NSO2, [M+Na]+ : ; found, phenyl-2-tosylethanone (4aa)1 1 H NMR (400 MHz, CDCl3) δ 7.94 (d, J = 7.7 Hz, 2H), 7.76 (d, J = 8.1 Hz, 2H), 7.61 (t, J = 7.4 Hz, 1H), 7.47 (t, J = 7.7 Hz, 2H), 7.32 (d, J = 8.0 Hz, 2H), 4.71 (s, 2H), 2.43 (s, 3H). 13C NMR (100 MHz, CDCl3) δ 188.5, 145.4, 135.8, 135.8, 134.3, 129.8, 129.3, 128.8, 128.6, 63.3, IR (KBr) ν (cm-1) 2926, 1679, 1319, 1150, 745. MS (EI, 70 ev) m/z (%): 274 (M+), 210, 155, 105, 91, (p-tolyl)-2-tosylethanone (4ba) 1 1 H NMR (400 MHz, CDCl3) δ 7.83 (d, J = 8.2 Hz, 2H), 7.75 (d, J = 8.2 Hz, 2H), 7.31 (d, J = 8.1 Hz, 2H), 7.25 (d, J = 8.0 Hz, 2H), 4.69 (s, 2H), 2.42 (s, 3H), 2.40 (s, 3H). 13C NMR (100 MHz, CDCl3) δ 187.7, 145.5, 145.3, 135.9, 133.4, 129.8, 129.5, 129.5, 128.6, 63.5, 21. 8, IR (KBr) ν (cm-1) 2925, 1678, 1322, 1154, 778. MS (EI, 70 ev) m/z (%): 288 (M+), 224, 119, 91, (4-methoxyphenyl)-2-tosylethanone (4ca) 1 H NMR (400 MHz, CDCl3) δ 7.92 (d, J = 8.6 Hz, 2H), 7.75 (d, J = 8.0 Hz, 2H), 7.32 (d, J = 7.9 Hz, 2H), 6.93 (d, J = 8.6 Hz, 2H), 4.66 (s, 2H), 3.87 (s, 3H), 2.42 (s, 3H). 13C NMR (100 MHz, CDCl3) δ 186.4, 164.6, 145.2, 135.9, 131.9, 129.8, 128.9, , 114.1, 63.5, 55.6, IR (KBr) ν (cm-1) 3066, 2943, 1599, 1320, MS (EI, 70 ev) m/z (%): 304 (M+), 281, 240, 207, 135, 91, 77. HRMS-ESI (m/z): calcd for C16H16SO4, [M+Na]+ : ; found,
5 1-(4-fluorophenyl)-2-tosylethanone (4da) 1 H NMR (400 MHz, CDCl3) δ (m, 2H), 7.74 (d, J = 8.2 Hz, 2H), 7.34 (d, J = 8.1 Hz, 2H), 7.15 (t, J = 8.5 Hz, 2H), 4.68 (s, 2H), 2.44 (s, 3H). 13C NMR (100 MHz, CDCl3) δ 186.6, 166.4(d, J = 254 Hz), 145.5, 135.7, 132.3, 132.2, 129.9, , 116.1(d, J = 22 Hz), 63.8, IR (KBr) ν (cm-1) 2944, 1680, 1321, 1155, 1024, 811. MS (EI, 70 ev) m/z (%): 292 (M+), 228, 155, 123, 91, 65. HRMS-ESI (m/z): calcd for C15H13FSO3, [M+Na]+ : ; found, (4-chlorophenyl)-2-tosylethanone (4ea)1 1 H NMR (400 MHz, CDCl3) δ 7.88 (d, J = 8.5 Hz, 2H), 7.73 (d, J = 8.2 Hz, 2H), 7.43 (d, J = 8.5 Hz, 2H), 7.32 (d, J = 8.0 Hz, 2H), 4.68 (s, 2H), 2.43 (s, 3H). 13C NMR (100 MHz, CDCl3) δ 187.1, 145.6, , 134.1, 130.8, 129.9, 129.2, 128.5, 63.7, IR (KBr) ν (cm-1) 2926, 1683, 1321, 1152, 813. MS (EI, 70 ev) m/z (%): 308 (M+), 244, 155, 139, 108, 91, (4-bromophenyl)-2-tosylethanone(4fa) H NMR (400 MHz, CDCl3) δ 7.80 (d, J = 8.5 Hz, 2H), 7.73 (d, J = 8.2 Hz, 2H), 7.61 (d, J = 8.5 Hz, 2H), 7.33 (d, J = 8.1 Hz, 2H), 4.68 (s, 2H), 2.44 (s, 3H). 13C NMR (100 MHz, CDCl3) δ 187.3, 145.6, 135.6, 134.5, 132.2, 130.8, 129.9, 128.6, 63.7, IR (KBr) ν (cm-1) 2926, 1681, 1320, 1152, 524. MS (EI, 70 ev) m/z (%): 352 (M+), 281, 207, 193, 135, 105, 91, 73. HRMS-ESI (m/z): calcd for C15H13BrSO3, [M+Na]+ : ; found, (4-iodophenyl)-2-tosylethanone (4ga) 1 H NMR (400 MHz, CDCl3) δ 7.85 (d, J = 8.4 Hz, 2H), 7.73 (d, J = 8.1 Hz, 2H), 7.65 (d, J = 8.4 Hz, 2H), 7.34 (d, J = 8.0 Hz, 2H), 4.66 (s, 2H), 2.45 (s, 3H). 13C NMR (100 MHz, CDCl3) δ 187.6, 145.5, 138.2, 135.7, 135.1, 130.6, 129.9, 128.6, 102.3, 63.7, IR (KBr) ν (cm-1) 2925, 1678, 1386, 1152, 523. MS (EI, 70 ev) m/z (%): 400 (M+), 355, 279, 176, 132, 105, 73. HRMS-ESI (m/z): calcd for C15H13ISO3, [M+Na]+ : ; found, (4-nitrophenyl)-2-tosylethanone (4ha)4 1 H NMR (400 MHz, CDCl3) δ 8.30 (d, J = 8.7 Hz, 2H), 8.13 (d, J = 8.7 Hz, 2H), 7.74 (d, J = 8.1 Hz, 2H), 7.35 (d, J = 7.9 Hz, 2H), 4.76 (s, 2H), 2.45 (s, 3H). 13C NMR (100 MHz, CDCl3) δ 187.1, 150.4, 145.9, 140.0, 135.4, 130.5, 130.1, , 64.1, IR (KBr) ν (cm-1) 2924, 1684, 1518, 1315, 1248, 1149, 806. MS (EI, 70 ev) m/z (%): 319 (M+), 281, 224, 207, 180, 119, 91, tosyl-1-(4-(trifluoromethyl)phenyl)ethanone (4ia) 1 H NMR (400 MHz, CDCl3) δ 8.06 (d, J = 7.4 Hz, 2H), 7.73 (d, J = 7.4 Hz, 4H), 7.33 (d, J = 7.3 Hz, 2H), 4.74 (s, 2H), 2.44 (s, 3H). 13C NMR (100 MHz, CDCl3) δ 187.5, 145.7, 138.4, 135.6, 135.2, 123.0, 129.7, 128.5, 125.9, 125.8, 63.9, IR (KBr) ν (cm-1) 2928, 1687, 1322, MS (EI, 70 ev) m/z (%): 342 (M+), 323, 278, 173, 145, 91, 65. HRMS-ESI (m/z): calcd for C16H13F3SO4, [M+Na]+ : ; found,
6 1-(2-fluorophenyl)-2-tosylethanone (4ma) 1 H NMR (400 MHz, CDCl 3 ) δ 7.79 (t, J = 10.5 Hz, 3H), 7.56 (d, J = 5.5 Hz, 1H), 7.32 (d, J = 7.5 Hz, 2H), (m, 1H), (m, 1H), 4.78 (s, 2H), 2.43 (s, 3H). 13 C NMR (100 MHz, CDCl 3 ) δ 185.9, 162.0(d, J = 354 Hz), 145.2, 136.3, 136.0(d, J = 9Hz), 131.2, 129.8, 128.6, 124.8(d, J = 3 Hz), 116.8(d, J = 24 Hz), 67.2, 67.1, IR (KBr) ν (cm -1 ) 2925, 1684, 1323, 1153, 761, 512. MS (EI, 70 ev) m/z (%): 292 (M+), 228, 155, 123, 91. HRMS-ESI (m/z): calcd for C 15 H 13 FSO 3, [M+Na]+ : ; found, (2-methoxyphenyl)-2-tosylethanone (4na) 1 H NMR (400 MHz, CDCl 3 ) δ 7.73 (d, J = 8.1 Hz, 2H), 7.64 (d, J = 7.8 Hz, 1H), 7.47 (t, J = 7.8 Hz, 1H), (m, 2H), 6.97 (t, J = 7.5 Hz, 1H), 6.88 (d, J = 8.4 Hz, 1H), 4.91 (s, 2H), 3.85 (s, 3H), 2.40 (s, 3H). 13 C NMR (100MHz, CDCl 3 ) δ 189.2, 159.0, 144.8, 136.7, 135.2, 131.2, 129.5, 128.5, 126.3, 120.9, 111.7, 67.5, 55,7, IR (KBr) ν (cm -1 ) 3360, 2944, 1672, 1300, 1021, 754. MS (EI, 70 ev) m/z (%): 304 (M+), 240, 207, 135, 91, 77. HRMS-ESI (m/z): calcd for C 16 H 16 SO 4, [M+Na]+ : ; found, (m-tolyl)-2-tosylethanone (4oa) 1 H NMR (400 MHz, CDCl 3 ) δ (m, 4H), 7.40 (d, J = 7.5 Hz, 1H), 7.33 (dd, J = 14.8, 7.7 Hz, 3H), 4.70 (s, 2H), 2.42 (s, 3H), 2.37 (s, 3H). 13 C NMR (100 MHz, CDCl 3 ) δ 188.3, 145.3, 138.7, , 135.8, 135.1, 129.8, 129.7, 128.7, 128.6, 126.6, 63.5, 21.7, IR (KBr) ν (cm -1 ) 2922, 1677, 1318, 1151, 769. MS (EI, 70 ev) m/z (%): 288 (M+), 224, 155, 119, 91, 65. HRMS-ESI (m/z): calcd for C 16 H 16 SO 3, [M+Na]+ : ; found, (3-fluorophenyl)-2-tosylethanone (4pa) 1 H NMR (400 MHz, CDCl 3 ) δ 7.75 (d, J = 8.3 Hz, 3H), (m, 1H), 7.47 (td, J = 8.0, 5.5 Hz, 1H), (m, 3H), 4.69 (s, 2H), 2.45 (s, 3H). 13 C NMR (100 MHz, CDCl 3 ) δ 187.1, 162.8(d, J = 247 Hz), 145.6, 137.8, (d, J = 6 Hz), 135.7, 130.6(d, J = 8 Hz), 129.9, 128.6, 125.3(d, J = 3 Hz), 121.4(d, J = 21 Hz), 115.8(d, J = 23 Hz), 63.8, IR (KBr) ν (cm -1 ) 2930, 1686, 1323, 1152, 777. MS (EI, 70 ev) m/z (%): 292 (M+), 228, 155, 123, 91, 65. HRMS-ESI (m/z): calcd for C 15 H 13 FSO 3, [M+Na]+ : ; found, (3-chlorophenyl)-2-tosylethanone (4qa) 1 H NMR (400 MHz, CDCl 3 ) δ 7.76 (dd, J = 7.2, 1.1 Hz, 2H), 7.67 (d, J = 8.3 Hz, 2H), (m, 1H), 7.34 (t, J = 8.2 Hz, 1H), 7.25 (d, J = 8.1 Hz, 2H), 4.61 (s, 2H), 2.36 (s, 3H). 13 C NMR (100 MHz, CDCl 3 ) δ 187.1, 145.6, 137.3, 135.6, 135.2, 134.2, 130.2, 129.9, 129.1, 128.6, 127.6, 63.7, IR (KBr) ν (cm -1 ) 2927, 1681, 1320, 1153, 772. MS (EI, 70 ev) m/z (%): 308 (M+), 244, 155, 139, 91, 65. HRMS- ESI (m/z): calcd for C 15 H 13 ClSO 3, [M+Na]+ : ; found, (3-bromophenyl)-2-tosylethanone (4ra) 1 H NMR (400 MHz, CDCl 3 ) δ 8.00 (t, J = 1.8 Hz, 1H), (m, 1H), (m, 3H), 7.36 (dd, J = 15.1, 7.8 Hz, 3H), 4.67 (s, 2H), 2.45 (s, 3H). 13 C NMR (100 MHz, CDCl 3 ) δ 187.0, 145.6, 137.4, 137.1, 135.6, 132.1, 130.4, 129.9, 128.6, 128.0, 123.2, 63.7, IR 4
7 (KBr) ν (cm-1) 2924, 1682, 1320, 1152, 769. MS (EI, 70 ev) m/z (%): 352 (M+), 288, 207, 183, 108, 91, 65. HRMS-ESI (m/z): calcd for C15H13BrSO3, [M+Na]+ : ; found, (3,4-dimethylphenyl)-2-tosylethanone (4sa) 1 H NMR (400 MHz, CDCl3) δ 7.75 (d, J = 7.8 Hz, 2H), 7.66 (s, 2H), 7.31 (d, J = 7.9 Hz, 2H), 7.21 (d, J = 8.4 Hz, 1H), 4.68 (s, 2H), 2.42 (s, 3H), 2.30 (s, 3H), 2.28 (s, 3H). 13C NMR (100 MHz, CDCl3) δ 187.9, 145.2, 144.3, 137.3, 136.0, 133.8, 130.3, 130.1, 129.8, 128.6, 127.2, 63.5, 21. 7, 20.1, IR (KBr) ν (cm-1) 2924, 1675, 1318, 1152, 863. MS (EI, 70 ev) m/z (%): 302 (M+), 238, 207, 133, 91, 77. HRMSESI (m/z): calcd for C17H18SO3, [M+Na]+ : ; found, phenyl-2-tosylpropan-1-one (4ua) 1 H NMR (400 MHz, CDCl3) δ 7.98 (d, J = 7.9 Hz, 2H), 7.66 (d, J = 7.7 Hz, 2H), 7.61 (t, J = 7.4 Hz, 1H), 7.48 (t, J = 7.4 Hz, 2H), 7.31 (d, J = 7.9 Hz, 2H), 5.15 (q, J = 6.9 Hz, 1H), 2.43 (s, 3H), 1.56 (d, J = 6.9 Hz, 3H). 13C NMR (100 MHz, CDCl3) δ 192.6, 145.3, 136.3, 134.0, 133.1, 129.9, 129.5, 129.2, 128.7, 65.1, 21.7, IR (KBr) ν (cm-1) 2925, 1680, 1313, 1145, 734. MS (EI, 70 ev) m/z (%): 288 (M+), 244, 155, 105, 91, 77. HRMS-ESI (m/z): calcd for C16H16SO3, [M+Na]+ : ; found, phenyl-2-tosylbutan-1-one (4va) 1 H NMR (400 MHz, CDCl3) δ 7.96 (d, J = 7.8 Hz, 2H), 7.65 (d, J = 7.9 Hz, 2H), 7.59 (t, J = 7.4 Hz, 1H), 7.47 (t, J = 7.5 Hz, 2H), (m, 2H), 5.00 (dd, J = 10.7, 3.5 Hz, 1H), 2.41 (s, 3H), (m, 2H), 0.87 (t, J = 7.4 Hz, 3H). 13C NMR (100 MHz, CDCl3) δ 192.8, 145.3, , 134.0, 133.5, 129.8, 129.5, 129.0, 128.8, 71. 5, , IR (KBr) ν (cm-1) 2936, 1681, 1315, 1144, 754. MS (EI, 70 ev) m/z (%): 302 (M+), 274, 238, 146, 105, 77. HRMS-ESI (m/z): calcd for C17H18SO3, [M+Na]+ : ; found, (thiophen-2-yl)-2-tosylethanone (4wa) 1 H NMR (400 MHz, CDCl3) δ 7.81 (d, J = 3.8 Hz, 1H), 7.75 (t, J = 7.2 Hz, 3H), 7.33 (d, J = 8.0 Hz, 2H), 7.14 (dd, J = 12.2, 8.0 Hz, 1H), 4.61 (s, 2H), 2.43 (s, 3H). 13C NMR (100 MHz, CDCl3) δ 180.3, 145.5, 143.2, 136.4, 135.6, 135.3, 129.9, 128.7, 128.6, 64.7, IR (KBr) ν (cm-1) 2933, 1653, 1385, 1149, 725. MS (EI, 70 ev) m/z (%): 280 (M+), 216, 155, 111, 108, 65. HRMS-ESI (m/z): calcd for C13H12S2O3, [M+Na]+ : ; found, phenyl-2-(phenylsulfonyl)ethanone (4ab) 1 H NMR (400 MHz, CDCl3) δ 7.90 (dd, J = 12.1, 7.9 Hz, 4H), (m, 2H), 7.53 (t, J = 7.6 Hz, 2H), 7.46 (t, J = 7.6 Hz, 2H), 4.74 (s, 2H). 13C NMR (100 MHz, CDCl3) δ 188.0, 138.8, 135.8, 134.4, 134.2, 129.3, 129.2, 128.9, 128.6, IR (KBr) ν (cm-1) 2929, 1679, 1318, 1153, 743. MS (EI, 70 ev) m/z (%): 260 (M+), 196, 141, 125, 105, 77. HRMS-ESI (m/z): calcd for C14H12SO3, [M+Na]+ : ; found,
8 2-((4-fluorophenyl)sulfonyl)-1-phenylethanone (4ac) 1 H NMR (400 MHz, CDCl 3 ) δ (m, 4H), (m, 1H), 7.47 (t, J = 7.6 Hz, 2H), 7.20 (t, J = 8.4 Hz, 2H), 4.74 (s, 2H). 13 C NMR (100MHz, CDCl 3 ) δ 188.1, 166.1(d, J = 256 Hz), 135.7, 134.7, 134.5, 131.7(d, J = 10 Hz), 129.2, 128.9, (d, J = 23 Hz), IR (KBr) ν (cm -1 ) 2927, 1679, 1326, 1152, 751. MS (EI, 70 ev) m/z (%): 278 (M+), 214, 159, 105, 95, 77. HRMS-ESI (m/z): calcd for C 14 H 11 FSO 3, [M+Na]+ : ; found, ((4-chlorophenyl)sulfonyl)-1-phenylethanone (4ad) 1 H NMR (400 MHz, CDCl 3 ) δ 7.93 (d, J = 7.9 Hz, 2H), 7.83 (d, J = 8.4 Hz, 2H), 7.63 (t, J = 7.3 Hz, 1H), (m, 4H), 4.74 (s, 2H). 13 C NMR (100 MHz, CDCl 3 ) δ 187.9, 141.1, 137.1, 135.6, 134.6, 130.2, 129.5, 129.3, 129.0, IR (KBr) ν (cm -1 ) 2954, 1683, 1310, 1143, 748. MS (EI, 70 ev) m/z (%): 294(M+), 230, 175, 128, 105, 77. HRMS-ESI (m/z): calcd for C 14 H 11 ClSO 3, [M+Na]+ : ; found, ((4-bromophenyl)sulfonyl)-1-phenylethanone (4ae) 2 1 H NMR (400 MHz, CDCl 3 ) δ 7.93 (d, J = 7.9 Hz, 2H), 7.75 (d, J = 8.5 Hz, 2H), 7.68 (d, J = 8.3 Hz, 2H), 7.64 (t, J = 6.8 Hz, 1H), 7.49 (t, J = 7.6 Hz, 2H), 4.74 (s, 2H). 13 C NMR (100 MHz, CDCl 3 ) δ 187.9, 137.7, 135.6, , 132.5, 130.2, 129.8, 129.3, 129.0, IR (KBr) ν (cm -1 ) 2923, 1652, 1316, 1244, 1149, 746. MS (EI, 70 ev) m/z (%): 338 (M+), 274, 174, 155, 105, ((4-methoxyphenyl)sulfonyl)-1-phenylethanone (4af) 1 H NMR (400 MHz, CDCl 3 ) δ (m, 2H), (m, 2H), (m, 1H), 7.38 (dd, J = 10.7, 4.8 Hz, 2H), (m, 2H), 4.63 (s, 2H), 3.77 (s, 3H). 13 C NMR (100 MHz, CDCl 3 ) δ 188.3, 164.2, 135.8, 134.3, 130.9, 130.3, 129.3, 128.8, 114.4, 63.7, IR (KBr) ν (cm -1 ) 3368, 2945,1680,1321,1027,748. MS (EI, 70 ev) m/z (%): 290 (M+), 226, 171, 124, 105, 77. HRMS-ESI (m/z): calcd for C 15 H 14 SO 4, [M+Na]+ : ; found, phenyl-2-((4-(trifluoromethyl)phenyl)sulfonyl)ethanone (4ag) 1 H NMR (400 MHz, CDCl 3 ) δ 8.07 (dd, J = 19.0, 9.3 Hz, 2H), 7.93 (dd, J = 18.1, 10.8 Hz, 2H), 7.80 (t, J = 9.9 Hz, 2H), 7.63 (dd, J = 10.6, 4.3 Hz, 1H), (m, 2H), 4.79 (s, 2H). 13 C NMR (100 MHz, CDCl 3 ) δ 187.7,142.2, 135.8(d, J = 30 Hz), 135.5, 134.6, 129.4, 129.2, 129.0, 126.3(q, J = 3 Hz), 123.1(d, J =272 Hz), IR (KBr) ν (cm -1 ) 2933, 1678, 1319, 1146, 746. MS (EI, 70 ev) m/z (%): 328 (M+), 264, 145, 105, 91, 77. HRMS-ESI (m/z): calcd for C 15 H 11 F 3 SO 3, [M+Na]+ : ; found, Ph O O S O Cl 2-((2-chlorophenyl)sulfonyl)-1-phenylethanone (4ah) 1 H NMR (400 MHz, CDCl 3 ) δ (m, 1H), 7.94 (dd, J = 8.4, 1.2 Hz, 2H), (m, 3H), (m, 3H), 5.05 (s, 2H). 13 C NMR (100 MHz, CDCl 3 ) δ 187.8, 136.5, 135.8, 135.1, 134.4, 132.7, 132.1, 131.9, 129.2, 128.9, 127.5, IR (KBr) ν (cm -1 ) 2925, 1680, 1324, 1156, 752. MS (EI, 70 ev) m/z (%): 294 (M+), 230, 195, 128, 105, 77. HRMS-ESI (m/z): calcd for C 14 H 11 ClSO 3, [M+Na]+ : ; found, (naphthalen-2-ylsulfonyl)-1-phenylethanone (4ai) 6
9 1 H NMR (400 MHz, CDCl 3 ) δ 8.46 (s, 1H), (m, 6H), (m, 3H), (m, 2H), 4.81 (s, 2H). 13 C NMR (100 MHz, CDCl 3 ) δ 188.0, 135.8, 135.7, 135.6, 134.3, 132.0, 130.7, 129.6, 129.5, 129.5, 129.3, 128.8, 128.0, 127.7, 123.0, IR (KBr) ν (cm -1 ) 2922, 1652, 1314, 1153, 749. MS (EI, 70 ev) m/z (%): 310 (M+), 246, 207, 144, 127, 105, 77. HRMS-ESI (m/z): calcd for C 18 H 14 SO 3, [M+Na]+ : ; found, (methylsulfonyl)-1-phenylethanone (4aj) 3 1 H NMR (400 MHz, CDCl 3 ) δ 7.98 (d, J = 7.9 Hz, 2H), 7.63 (t, J = 7.4 Hz, 1H), 7.50 (t, J = 7.7 Hz, 2H), 4.61 (s, 2H), 3.12 (s, 3H). 13 C NMR (101 MHz, CDCl 3 ) δ 189.3, 135.7, 134.7, 129.2, 129.0, 61.2, IR (KBr) ν (cm -1 ) 2924, 1652, 1244, MS (EI, 70 ev) m/z (%): 198 (M+), 105, 91, (ethylsulfonyl)-1-phenylethanone (4ak) 1 H NMR (400 MHz, CDCl 3 ) δ 8.01 (d, J = 7.8 Hz, 2H), 7.64 (t, J = 7.4 Hz, 1H), 7.51 (t, J = 7.7 Hz, 2H), 4.58 (s, 2H), 3.28 (q, J = 7.4 Hz, 2H), 1.45 (t, J = 7.4 Hz, 3H). 13 C NMR (100 MHz, CDCl 3 ) δ 189.3, , 134.6, 129.3, 129.0, 58. 8, 48.3, 6.6. IR (KBr) ν (cm -1 ) 2941, 1680, 1315, MS (EI, 70 ev) m/z (%): 212 (M+), 147, 120, 105, 77. HRMS-ESI (m/z): calcd for C 10 H 12 SO 3, [M+Na]+ : ; found, Ph O O S O 2-(cyclopropylsulfonyl)-1-phenylethanone (4al) 1 H NMR (400 MHz, CDCl 3 ) δ 8.00 (d, J = 7.7 Hz, 2H), 7.62 (t, J = 7.2 Hz, 1H), 7.50 (t, J = 7.3 Hz, 2H), 4.64 (s, 2H), (m, 1H), 1.24 (s, 2H), 1.06 (d, J = 7.3 Hz, 2H). 13 C NMR (100 MHz, CDCl 3 ) δ 188.9, 135.8, 134.5, 129.3, 129.0, 61.0, 30.9, 5.5. IR (KBr) ν (cm -1 ) 2948, 1682, 1322, 1142, 753. MS (EI, 70 ev) m/z (%): 224 (M+), 176, 145, 119, 105, 77. HRMS-ESI (m/z): calcd for C 11 H 12 SO 3, [M+Na]+ : ; found, A single crystal of product 3ta References 1. Anil. Kuma, M. K. Muthyala, Tetrahedron Lett. 2011, 52, H. Loghmani-Khouzani, M. R. Poorheravi, M. M. M. Sadeghi, L. Caggiano, R. F.W. Jackson, Tetrahedron, 2008, 64, N. Suryakiran, P. Prabhakar, K. Rajesh, V. Suresh, Y. Venkateswarlu, Journal of Molecular Catalysis A: Chemical. 2007, 207, C. Curti, M. Laget, A. O. Carle, A. Gellis, P. Vanelle, European Journal of Medicinal Chemistry, 2007, 42,
10 NMR Spectra for all Compounds 3aa 8
11 9
12 3ja 10
13 11
14 3ka 12
15 13
16 3la 14
17 15
18 3ta 16
19 17
20 4aa 18
21 19
22 4ba 20
23 21
24 4ca 22
25 23
26 4da 24
27 25
28 4ea 26
29 27
30 4fa 28
31 29
32 4ga 30
33 31
34 4ha 32
35 33
36 4ia 34
37 35
38 4ma 36
39 37
40 4na 38
41 39
42 4oa 40
43 41
44 4pa 42
45 43
46 4qa 44
47 45
48 4ra 46
49 47
50 4sa 48
51 49
52 4ua 50
53 51
54 4va 52
55 53
56 4wa 54
57 55
58 4ab 56
59 57
60 4ac 58
61 59
62 4ad 60
63 61
64 4ae 62
65 63
66 4af 64
67 65
68 4ag 66
69 67
70 4ah 68
71 69
72 4ai 70
73 71
74 4aj 72
75 73
76 4ak 74
77 75
78 4al 76
79 77
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