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The Journal of Organic Chemistry
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134.9, 131.7, 128.5, 127.7, 122.3 (d, JCꢀF = 7.1 Hz), 115.3 (d, JCꢀF = 21.6 Hz ) ppm;
MS (70 eV): m/z (%)215 (M+, 40), 123 (100).
N-(4-Chlorophenyl)benzamide (3ah).13 The reaction of 1,2ꢀdiphenylethanꢀ1ꢀone
(1a, 0.50 mmol, 98 mg), 4ꢀchloroaniline (2h, 0.25 mmol, 32 mg), CuCl2·2H2O (0.025
mmol, 4.3 mg), 1,10ꢀphenanthroline monohydrate (0.050 mmol, 9.9 mg), in
acetonitrile (2.0 mL) for 36 h under typical procedure afforded 113 mg (97%) of 3ah
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as solid; m.p.: 208ꢀ209 oC; 1H NMR (DMSOꢀd6, 400 MHz):
J = 7.36 Hz, 2H), 7.82 (d, J = 9.0 Hz, 2H), 7.60 (t, J = 7.4 Hz, 1H), 7.54 (t, J = 7.4 Hz,
2H), 7.41 (d, J = 9.0 Hz, 2H); 13C NMR (DMSOꢀd6, 125 MHz):
= 165.8, 138.3,
δ = 10.37 (s, 1H), 7.95 (d,
δ
134.8, 131.8, 128.6, 128.5, 127.8, 127.4, 121.9 ppm; MS (70 eV): m/z (%) 231 (M+,
35Cl, 40), 233 (M+, 37Cl, 36), 105 (100).
N-(4-Bromophenyl)benzamide (3ai).14 The reaction of 1,2ꢀdiphenylethanꢀ1ꢀone
(1a, 0.50 mmol, 98 mg), 4ꢀbromoaniline (2i, 0.25 mmol, 43 mg), CuCl2·2H2O (0.025
mmol, 4.3 mg), 1,10ꢀphenanthroline monohydrate (0.05 mmol, 9.9 mg), in acetonitrile
(2.0 mL) for 24 h under typical procedure afforded 122 mg (88%) of 3ai as solid;
m.p.: 208ꢀ209 oC; 1H NMR (DMSOꢀd6, 400 MHz): δ = 10.37 (s, 1H), 7.95 (d, J = 7.2
Hz, 2H), 7.77 (d, J = 8.8 Hz, 2H), 7.63ꢀ7.50 (m, 5H); 13C NMR (DMSOꢀd6, 100
MHz): δ = 165.7, 138.7, 134.8, 131.8, 131.5, 128.5, 127.8, 122.3, 115.4 ppm; MS (70
eV): m/z (%)275 (M+, 78Br, 40), 277 (M+, 80Br, 36), 105 (100).
N-(2-Bromophenyl)benzamide (3aj).17 The reaction of 1,2ꢀdiphenylethanꢀ1ꢀone
(1a, 0.50 mmol, 98 mg), 2ꢀbromoaniline (2j, 0.25 mmol, 43 mg), CuCl2·2H2O (0.025
mmol, 4.3 mg), 1,10ꢀphenanthroline monohydrate (0.050 mmol, 9.9 mg), in
acetonitrile (2.0 mL) for 36 h under typical procedure afforded 121 mg (88%) of 3aj
as solid; m.p.: 96ꢀ97 oC; 1H NMR (DMSOꢀd6, 400 MHz): δ = 10.04 (s, 1H), 7.99 (d, J
= 6.4 Hz, 2H), 7.72 (d, J = 7.0 Hz, 1H), 7.63ꢀ7.51 (m, 4H), 7.43 (t, J = 7.0 Hz, 1H),
7.23 (t, J = 7.0 Hz, 1H); 13C NMR (DMSOꢀd6, 100 MHz):δ = 165.7, 138.7, 134.8,
131.8, 131.5, 128.5, 127.8, 122.3, 115.4ppm; MS (70 eV); m/z (%)275 (M+, 78Br, 40),
277 (M+, 80Br, 36), 105 (100).
N-(2-Iodophenyl)benzamide (3ak).18 The reaction of 1,2ꢀdiphenylethanꢀ1ꢀone (1a,
0.50 mmol, 98 mg), 2ꢀiodoaniline (2k, 0.25 mmol, 55 mg), CuCl2·2H2O (0.025 mmol,
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