10.1002/ejoc.201801473
European Journal of Organic Chemistry
COMMUNICATION
11924–11927; c) M. V. Leskinen, K. T. Yip, A. Valkonen, P.
M. Pihko, J. Am. Chem. Soc. 2012, 134, 5750–5753; d) J.-
C. Wu, R.-J. Song, Z.-Q. Wang, X.-C. Huang, Y.-X. Xie, J.-
H. Li, Angew. Chem. Int. Ed. 2012, 51, 3453–3457; Angew.
Chem. 2012, 124, 3509–3513; e) Y. Li, T. Yan, K. Junge,
M. Beller, Angew. Chem. Int. Ed. 2014, 53, 10476–10480;
Angew. Chem. 2009, 126, 10644–10648; f) Y. Li, W. -H.
Wang, S.-D. Yang, B.-J. Li, C. Feng, Z.-J. Shi, Chem.
Commun. 2010, 46, 4553–4555.
[5] a) D. R. Stuart, E. Villemure, K. Fagnou, J. Am. Chem. Soc.
2007, 129, 12072–12073; b) D. J. Schipper, M. Hutchinson,
K. Fagnou, J. Am. Chem. Soc. 2010, 132, 6910–6911; c)
M. Nishino, K. Hirano, T. Satoh, M. Miura, Angew. Chem.
Int. Ed. 2012, 51, 6993–6997; Angew. Chem. 2012, 124,
7099–7103; d) Z. Ding, N. Yoshikai, Angew. Chem. Int. Ed.
2012, 51, 4698–4701; Angew. Chem. 2012, 124, 4776–
4779; e) S. Islam, I. Larrosa, Chem. Eur. J. 2013, 19,
15093–15096; f) H. Ikemoto, T. Yoshino, K. Sakata, S.
Matsunaga, M. Kanai, J. Am. Chem. Soc. 2014, 136,
5424–5431; g) D. Zhao, J. H. Kim, L. Stegemann, C. A.
Strassert, F. Glorius, Angew. Chem. Int. Ed. 2015, 54,
4508–4511; Angew. Chem. 2015, 127, 4591–4594; h) M.
Moselage, N. Sauermann, S. C. Richter, L. Ackermann,
Angew. Chem. Int. Ed. 2015, 54, 6352–6355; Angew.
Chem. 2015, 127, 6450–6453; i) D.-G. Yu, T. Gensch, F.
de Azambuja, S. Vasquez-Cespedes, F. Glorius, J. Am.
Chem. Soc. 2014, 136, 17722–17725; j) F. Xie, Z. S. Qi, S.
Yu, X. Li, J. Am. Chem. Soc. 2014, 136, 4780–4787; k) J.
Li, L. Ackermann, Angew. Chem. Int. Ed. 2015, 54, 3635–
3638; Angew. Chem. 2015, 127, 8671–8674.
[6] a) S. Paul, G. A. Chotana, D. Holmes, R. C. Reichle, R. E.
Maleczka, M. R. Smith, J. Am. Chem. Soc. 2006, 128,
15552–15553; b) D. W. Robbins, T. A. Boebel, J. F.
Hartwig, J. Am. Chem. Soc. 2010, 132, 4068–4069; c) Y.
Feng, D. Holte, J. Zoller, S. Umemiya, L. R. Simke, P. S.
Baran, J. Am. Chem. Soc. 2015, 137, 10160–10163; d) Q.
Liu, Q. Li, Y. Ma, Y. Jia, Org. Lett. 2013, 15, 4528–4531; e)
V. Lanke, K. R. Prabhu, Org. Lett. 2013, 15, 6262–6265; f)
G. Yang, P. Lindovska, D. Zhu, J. Kim, P. Wang, R.-Y.
Tang, M. Movassaghi, J.-Q. Yu, J. Am. Chem. Soc. 2014,
136, 10807–10813; g) V. Lanke, K. R. Bettadapur, K. R.
Prabhu, Org. Lett. 2016,18, 5496–5499; h) L. Xu, C. Zhang,
Y. He, L. Tan, D. Ma, Angew. Chem. Int. Ed. 2016, 55,
321–325; Angew. Chem. 2016, 128, 329–333; i) Y. Kim, J.
Park, S. Chang, Org. Lett. 2016, 18, 1892–1895; j) Z. Song,
A. P. Antonchick, Org. Biomol. Chem. 2016, 14, 4804–
4808; k) L. Xu, L. S. Tan, D. Ma, J. Org. Chem. 2016, 81,
10476–10483; l) L. Ping, D. S. Chung, J. Bouffard, S. G.
Lee, Chem. Soc. Rev. 2017, 46, 4299–4328; m) Y. Yang,
Z. Shi, Chem. Commun. 2018, 54, 1676–1685.
[7] a) J. A. Homer, J. Sperry, Tetrahedron Lett. 2014, 55,
5798–5800; b) R. P. Loach, O. S. Fenton, K. Amaike, D. S.
Siegel, E. Ozkal, M. Movassaghi, J. Org. Chem. 2014, 79,
11254–11263; c) A. K. Pitts, F. O'Hara, R. H. Snell, M. J.
Gaunt, Angew. Chem. Int. Ed. 2015, 54, 5451–5455;
Angew. Chem. 2015, 127, 5541–5545.
[8] Y. Yang, X. Qiu, Y. Zhao, Y. Mu, Z. Shi, J. Am. Chem. Soc.
2016,138, 495–498.
[9] J. A. Leitch, C. L. McMullin, M. F. Mahon, Y. Bhonoah, C.
G. Frost, Acs Catal. 2017, 7, 2616–2623.
[10] Y. Yang, R. Li, Y. Zhao, D. Zhao, Z. Shi, J. Am. Chem. Soc.
2016,138, 8734–8737.
[11] Y. Yang, P. Gao, Y. Zhao, Z. Shi, Angew. Chem. Int. Ed.
2017, 56, 3966–3971; Angew. Chem. 2017, 129, 4024–
4029.
[12] For selected examples on double C–H arylation of
heterocycles, see: a) A. Punzi, D. I. Coppi, S. Matera, M. A.
M. Capozzi, A. Operamolla, R. Ragni, F. Babudri, G. M.
Farinole, Org. Lett. 2017,19, 4754–4757; b) H. Jiang, A.
Bellomo, M. Zhang, P. J. Carroll, B. C. Manor, T. Jia, P. J.
Walsh, Org. Lett. 2018, 20, 2522–2525.
[13] A. J. Borah, Z. Shi, Chem. Commun. 2017, 53, 3945–3948.
[14] For one example on 1,2-migration of the benzyl group in
indoles, see: A. Suárez, M. Gohain, M. A. Fernández-
Rodríguez, R. Sanz, J. Org. Chem. 2015, 80, 10421–
10430.
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