K
G. Hong et al.
Paper
Synthesis
HRMS (ESI-TOF): m/z [M + H]+ calcd for C13H11FNO: 216.0825; found:
216.0829.
(2) Selected examples: (a) Yin, Z.; Jiang, X.; Sun, P. J. Org. Chem.
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N-(4-Bromophenyl)benzamide (7f)29
Yield: 36 mg (52%); pale yellow solid; mp 201–203 °C.
1H NMR (400 MHz, CDCl3): δ = 7.86 (d, J = 6.8 Hz, 2 H), 7.81 (s, 1 H),
7.58–7.47 (m, 7 H).
13C NMR (100 MHz, CDCl3): δ = 162.5, 134.5, 133.6, 132.0, 131.9,
130.1, 128.8, 126.9, 121.6. 117.1.
HRMS (ESI-TOF): m/z [M + H]+ calcd for C13H11BrNO: 276.0024; found:
276.0029.
(3) Li, H.; Li, P.; Wang, L. Org. Lett. 2013, 15, 620.
N-(p-Tolyl)benzamide (7g)27
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2014, 356, 519. (b) Chen, Z.; Wang, B.; Zhang, J.; Yu, W.; Liu, Z.;
Zhang, Y. Org. Chem. Front. 2015, 2, 1107.
Yield: 42 mg (79%); white solid; mp 158–160 °C.
1H NMR (400 MHz, CDCl3): δ = 7.85 (d, J = 8.0 Hz, 3 H), 7.52 (d, J = 8.4
Hz, 3 H), 7.49–7.43 (m, 2 H), 7.16 (d, J = 7.6 Hz, 2 H), 2.34 (s, 3 H).
13C NMR (100 MHz, CDCl3): δ = 165.7, 135.4, 135.1, 134.2, 131.7,
129.6, 128.7, 127.0, 120.3, 20.9.
HRMS (ESI-TOF): m/z [M + H]+ calcd for C14H14NO: 212.1075; found:
212.1078.
(7) Qian, C.; Lin, D.; Deng, Y.; Zhang, X.; Jiang, H.; Miao, G.; Zeng, W.
Org. Biomol. Chem. 2014, 12, 5866.
N-(3-Chlorophenyl)benzamide (7h)27
Yield: 34 mg (58%); pale yellow solid; mp 118–120 °C.
(8) Wuts, P. G. M.; Green, T. W. Protective Groups in Organic Synthe-
sis, 4th ed.; Wiley: New York, 2007, 102.
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75, 3507.
1H NMR (400 MHz, CDCl3): δ = 8.06 (br s, 1 H), 7.83 (d, J = 8.4 Hz, 2 H),
7.76 (s, 1 H), 7.54–7.42 (m, 4 H), 7.29–7.22 (m, 1 H), 7.10 (d, J = 8.0 Hz,
1 H).
13C NMR (100 MHz, CDCl3): δ = 166.0, 139.0, 134.7, 134.5, 132.1,
130.0, 128.8, 127.1, 124.6, 120.4, 118.3.
HRMS (ESI-TOF): m/z [M – H]+ calcd for C13H9ClNO: 230.0373; found:
230.0371.
(13) Shen, Z.; Dai, J.; Xiong, J.; He, X.; Mo, W.; Hu, B.; Sun, N.; Hu, X.
Adv. Synth. Catal. 2011, 353, 3031.
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(c) Shen, Z.; Dai, J.; Xiong, J.; He, X.; Mo, W.; Hu, B.; Sun, N.; Hu,
X. Adv. Synth. Catal. 2011, 353, 3031. (d) Nishiguchi, T.;
Bougauchi, M. J. Org. Chem. 1989, 54, 3001. (e) Khatun, N.;
Banerjee, A.; Santra, S. K.; Ali, W.; Patel, B. K. RSC Adv. 2015, 5,
36461.
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Bae, J. J.; Kwak, J. H.; Jung, Y. H.; Kim, I. S. J. Org. Chem. 2014, 79,
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Acknowledgment
This research was financially supported by the National Nature Sci-
ence Foundation of China (21272069, 20672035) and the Fundamen-
tal Research Funds for the Central Universities and Key Laboratory of
Organofluorine Chemistry, Shanghai Institute of Organic Chemistry,
Chinese Academy of Sciences.
Supporting Information
Supporting information for this article is available online at
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2009, 57, 3261. (b) Carey, J. S.; Laffan, D.; Thomson, C.;
Williams, M. T. Org. Biomol. Chem. 2006, 4, 2337. (c) Humphrey,
J. M.; Chamberlin, A. R. Chem. Rev. 1997, 97, 2243.
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© Georg Thieme Verlag Stuttgart · New York — Synthesis 2016, 48, A–L