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Organic & Biomolecular Chemistry
Page 5 of 6
DOI: 10.1039/C8OB00086G
Journal Name
ARTICLE
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equiv) and LiCl (12.7 mg, 1 equiv) in toluene (3 mL) in a Schlenk
Pressure Tube (10 mL) under a dry argon atmosphere, when
1a was fully consumed, changing DMF as the solvent. The
reaction mixture was vigorously stirred at 110 °C overnight.
After completion of the reaction, the solvent was removed
under pressure and the crude product was subjected to silica
gel column chromatography (eluent: petroleum ether / ethyl
acetate = 50 / 1) to afford the product 3u (72 mg, 65%).
tert-butyl 2,3-diphenyl-1H-indole-1-carboxylate (3s).
White solid (72.0 mg, 65%). mp: 115-117 oC. 1H NMR (400
MHz, CDCl3): δ 8.30 (d, J = 8.4 Hz, 1H), 7.57 (d, J = 7.6 Hz, 1H),
7.37 (t, J = 7.2 Hz, 1H), 7.26-7.19 (m, 11H), 1.24 (s, 9H),; 13C
NMR (101 MHz, CDCl3): δ 150.3, 136.6, 135.7, 133.9, 133.4,
130.3, 130.1, 129.3, 128.1, 127.7, 127.4, 126.6, 124.7, 123.0,
121.9, 119.6, 115.2, 83.3, 27.5.
J. Li, A-L. Ma, Y-N. Huang, J. Deng, J. Org. Chem., 2015, 80
,
3841; (h) A. Mizukami, Y. Ise, T. Kimachi, K. Inamoto, Org.
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Am. Chem. Soc., 2017, 139, 7749.
7
L. Huang, A. Biafora, G. Zhang, V. Bragoni, L. J. Gooβen,
Angew. Chem. Int. Ed., 2016, 55, 6933.
Conflicts of interest
8
9
O. Leogane, H. Lebel, Angew. Chem. Int. Ed., 2008, 47, 350.
(a) Q. Dai, P. Li, N. Ma, C. Hu, Org. Lett., 2016, 18, 5560; (b)
P. Li, N. Ma, J. Li, Z. Wang, Q. Dai, C. Hu, J. Org. Chem., 2017,
82, 8251.
There are no conflicts to declare.
Acknowledgements
10 D.-F. Lu, C.-L. Zhu, Z.-X. Jia, H. Xu, J. Am. Chem. Soc., 2014,
136, 13186.
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(b) T. Hundertmark, A. F. Littke, S. L. Buchwald, G. C. Fu, Org.
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13 Alexander Zapf, Angew. Chem. Int. Ed., 2003, 42, 5394.
14 Olivier Baudoin, Angew. Chem. Int. Ed., 2007, 46, 1373.
We thank the Excellent Young Scholars Research Fund of
Beijing
Institute
of
Technology
(3190012331518,
3190012331523), the National Natural Science Foundation of
China (21671019, 21231002), the 111 Project (B07012) and the
973 Program (2014CB932103) for financial support. We also
thank Analytical and Testing Center, Beijing Institute of
Technology.
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