Page 15 of 37
The Journal of Organic Chemistry
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2-((2-Aminophenyl)ethynyl)phenyl)(phenyl)methanone (1r). 475 mg, 80% yield;
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Orange oil; H NMR (400 MHz, CDCl ) δ (ppm) 7.86 (d, J = 7.6 Hz, 2H), 7.69 (d, J =
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.7 Hz, 1H), 7.61 – 7.57 (m, 1H), 7.54 – 7.45 (comp, 4H), 7.41 – 7.37 (m, 1H), 7.14
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(d, J = 7.5 Hz, 1H), 7.10 – 7.06 (m, 1H), 6.62 – 6.59 (m, 2H), 4.36 (br, 2H); C NMR
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(100 MHz, CDCl ) δ (ppm) 196.8, 149.0, 140.0, 137.5, 133.3, 133.1, 132.1, 130.8,
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30.5, 130.2, 129.5, 128.6, 127.4, 122.8, 117.3, 114.2, 107.1, 92.8, 91.8; HRMS (TOF
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MS ESI ) calculated for C H NO [M+H] : 298.1232, found 298.1231.
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(2-((2-Aminophenyl)ethynyl)phenyl)(p-tolyl)methanone (1s). 529 mg, 85% yield;
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Orange oil; H NMR (400 MHz, CDCl ) δ (ppm) 7.78 (d, J = 8.1 Hz, 2H), 7.69 (d, J =
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.6 Hz, 1H), 7.53 – 7.48 (m, 2H), 7.41 – 7.38 (m, 1H), 7.28 (d, J = 8.0 Hz, 2H), 7.16
(d, J = 7.8 Hz, 1H), 7.11 – 7.07 (m, 1H), 6.64 – 6.60 (m, 2H), 4.08 (br, 2H), 2.43 (s,
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H); C NMR (100 MHz, CDCl ) δ (ppm) 196.5, 149.0, 144.3, 140.4, 134.8, 132.9,
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32.1, 130.7, 130.5, 130.1, 129.3, 129.2, 127.4, 122.6, 117.3, 114.2, 107.1, 92.8, 91.6,
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21.8; HRMS (CI-TOF) m/z: [M+H] Calcd for C H NO 312.1388; Found 312.1389.
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(2-((2-Aminophenyl)ethynyl)phenyl)(4-bromophenyl)methanone (1t). 608 mg, 81%
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yield; Orange oil; H NMR (400 MHz, CDCl ) δ (ppm) 7.72 – 7.68 (comp, 3H), 7.60
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(d, J = 8.5 Hz, 2H), 7.54 – 7.50 (m, 1H), 7.47 (d, J = 7.2 Hz, 1H), 7.41 – 7.37 (m, 1H),
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7.14 – 7.12 (m, 1H), 7.11 – 7.07 (m, 1H), 6.64 – 6.60 (m, 2H), 4.43 (br, 2H); C
NMR (100 MHz, CDCl ) δ (ppm) 195.7, 149.0, 139.3, 136.2, 133.1, 132.1, 131.87,
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31.85, 131.0, 130.3, 129.4, 128.5, 127.5, 122.8, 117.4, 114.2, 106.9, 92.7, 92.1;
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HRMS (ESI-TOF) m/z: [M+H] Calcd for C H NOBr 376.0337; Found 376.0325.
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(2-((2-Aminophenyl)ethynyl)phenyl)(4-(trifluoromethyl)phenyl)methanone (1u). 584
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mg, 80% yield; Orange oil; H NMR (400 MHz, CDCl ) δ (ppm) 7.94 (d, J = 8.2 Hz,
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H), 7.74 – 7.70 (comp, 3H), 7.57 – 7.54 (m, 1H), 7.50 (d, J = 7.1 Hz, 1H), 7.43 –
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.39 (m, 1H), 7.11 – 7.08 (m, 2H), 6.66 – 6.60 (m, 2H), 4.23 (br, 2H); C NMR (100
MHz, CDCl ) δ (ppm) 195.6, 149.0, 140.6, 138.8, 134.4 (d, J = 32.7 Hz), 133.4, 132.1,
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31.5, 130.6, 130.4, 129.9, 127.6, 125.6 (q, J = 3.8 Hz), 123.7 (d, J = 272.8 Hz),
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23.2, 117.4, 114.3, 106.8, 92.7, 92.4; F NMR (376 MHz, CDCl ) δ – 63.05; HRMS
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(CI-TOF) m/z: [M+H] Calcd for C H NOF 366.1106; Found 366.1112.
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(2-((2-Aminophenyl)ethynyl)phenyl)(2-methoxyphenyl)methanone (1v). 562 mg, 86%
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