Please do not adjust margins
ChemComm
Page 4 of 4
COMMUNICATION
was produced and the catalyst is regenerated. The
Journal Name
D
Org. Chem. Front. 2018, 5, 2103.
DOI: 10.1039/C9CC08297B
(a) S. Duan, Y. Xu, X. Zhang and X. Fan, Chem. Commun.
aromatization of intermediate D gives the target compound 3aa.
3
2016, 52, 10529; (b) C. Huang and V. Gevorgyan, Org. Lett.
2010, 12, 2442; (c) Q. Xiao, Y. Zhang and J. Wang, Acc. Chem.
Res. 2013, 46, 236; (d) B. Schmidt and M. Riemer, J. Org. Chem.
2014, 79, 4104.
4
J. Y. Cho, G. B. Roh and E. J. Cho, J. Org. Chem. 2018, 83,
805.
5
(a) H. Gao, D. H. Ess, M. Yousufuddin and L. Kürti, J. Am.
Chem. Soc. 2013, 135, 7086; (b) L. Guo, F. Liu, L. Wang, H. Yuan,
L. Feng, L. Kürti and H. Gao, Org. Lett. 2019, 21, 2894. (c) S.
Shang, D. Zhang-Negrerie, Y. Du and K. Zhao, Angew. Chem.
Int. Ed. 2014, 53, 6216.
6
(a) J. Wencel-Delord, F. W. Patureau and F. Glorius, Top
Organomet Chem, 2015, 55, 1. (b) J. G. Kim, K. Shin and S.
Chang, Top Organomet Chem, 2015, 55, 29. (c) A. Peneau, C.
Guillou and L. Chabaud, Eur. J. Org. Chem. 2018, 2018, 5777.
(d) S. Rej and N. Chatani, Angew. Chem. Int. Ed.2019, 58, 8304.
7
(a) S. S. Zhang, C. Y. Jiang, J. Q. Wu, X. G. Liu, Q. Li, Z. S.
Huang, D. Li and H. Wang, Chem. Commun. 2015, 51, 10240;
(b) Z. Liu, J. Q. Wu and S. D. Yang, Org. Lett. 2017, 19, 5434; (c)
K. Wu, B. Cao, C. Y. Zhou and C. M. Che, Chemistry 2018, 24,
4815; (d) Y. S. Jang, L. Wozniak, J. Pedroni and N. Cramer,
Angew. Chem. Int. Ed. 2018, 57, 12901; (e) K. B. Somai
Magar, Edison, T. N. J., Y. R. Lee, Eur. J. Org. Chem., 2017, 7046.
(f) Y. Xiang, C. Wang, Q. Ding and Y. Peng, Adv. Synth. Catal.,
2019, 361, 919.
Scheme 3 Plausible reaction mechanism.
In summary, we have developed a facile strategy to build up the
biaryl scaffold through Ir(III)-catalyzed direct C−H bond
activation with a cascade intermolecular coupling. This strategy
can be proceeded under room temperature and features broad
generality and good atomic economy. Most importantly, this
strategy is the first to synthesize 2-amino-2′-hydroxy-1,1′-
biaryls by Ir(III)-catalyzed direct C-H bond functionalization.
We are grateful to the National Natural Science Foundation of
China (Nos. 21632008, 21672231, 21877118, and 81620108027)
and the Strategic Priority Research Program of the Chinese
Academy of Sciences (XDA12040107 and XDA12040201) for
financial support.
8
W. W. Chan, S. F. Lo, Z. Zhou and W. Y. Yu, J. Am. Chem.
Soc. 2012, 134, 13565.
(a) T. K. Hyster, K. E. Ruhl and T. Rovis, J. Am. Chem. Soc.
9
2013, 135, 5364; (b) Z. Shi, D. C. Koester, M. J. Am. Chem. Soc.
2013, 135, 12204; (c) J. Jeong, P. Patel, H. Hwang and S. Chang,
Org. Lett. 2014, 16, 4598; (d) Y. Liang, K. Yu, B. Li, S. Xu, H. Song
and B. Wang, Chem. Commun. 2014, 50, 6130; (e) J. Y. Son, S.
Kim, W. H. Jeon and P. H. Lee, Org. Lett. 2015, 17, 2518; (f) Y.
Li, Z. Qi, H. Wang, X. Yang and X. Li, Angew. Chem. Int. Ed. 2016,
55, 11877; (g) C. Song, C. Yang, F. Zhang, J. Wang and J. Zhu,
Org. Lett. 2016, 18, 4510; (h) X. Chen, S. Yang, H. Li, B. Wang
and G. Song, ACS Catal. 2017, 7, 2392; (i) H. Xie, Y. Shao, J. Gui,
J. Lan, Z. Liu, Z. Ke, Y. Deng, H. Jiang and W. Zeng, Org. Lett.
2019, 21, 3427. (j) S. Jin, Z. Chen and Y. Zhao, Adv. Synth. Catal.,
2019, 361, 4674. (k) S. Debbarma, M. R. Sk, B. Modak and M.
S. Maji, J. Org. Chem. 2019, 84, 6207. (l) K. Yan, Y. Lin, Y. Kong,
B. Li and B. Wang, Adv. Synth. Catal., 2019, 361, 1570. (m) P.
Patel and G. Borah, Chem. Commun, 2016, 53, 443. (n) Y. Zuo,
X. He, Y. Ning, Y. Wu and Y. Shang, ACS Omega, 2017, 2, 8507.
10 J. D. Moseley, P. M. Murray, E. R. Turp, S. N. G. Tyler and
R. T. Burn, Tetrahedron 2012, 68, 6010.
Conflicts of interest
There are no conflicts to declare.
Notes and references
1
(a) N. K. Daisuke Uraguchi, and Takashi Ooi, J. Am. Chem.
Soc. 2010, 132, 12240; (b) D. Uraguchi, T. Kizu, Y. Ohira, T. Ooi,
Chem. Commun. 2014, 50, 13489; (c) LinPu, Chem. Rev. 1998,
98, 2405; (d) Y. Chen, S. Y., and Andrei K. Yudin, Chem. Rev.
2003, 103, 3155; (e) P. Kočovský, Š. Vyskočil and M. Smrčina,
Chem. Rev. 2003, 103, 3213; (f) W. Fu and W. Tang, ACS Catal.
2016, 6, 4814; (g) J. Magano and J. R. Dunetz, Chem. Rev. 2011,
111, 2177; (h) M. Schmitkamp, W. Leitner and G. Franciò,
Catal. Sci. Technol. 2013, 3, 589; (i) K. Ding, H. Guo, X. Li, Y.
Yuan and Y. Wang, Top. Catal. 2005, 35, 105; (j) A. Desvergne,
E. Genin, X. Marechal, N. Gallastegui, L. Dufau, N. Richy, M.
Groll, J. Vidal and M. Reboud-Ravaux, J. Med. Chem. 2013, 56,
3367; (k) J. K. Yutaka Koguchi, M. Nishio, K. Takahashi, T.
Okuda, T. Ohnuki and S. Komatsubara, J. Antibio. 2000, 53,
105; (l) S. Mondal and P. R. Thompson, Acc. Chem. Res. 2019,
52, 818.
11 E. M. Simmons and J. F. Hartwig, Angew. Chem. Int. Ed.
2012, 51, 3066.
12 P. Patel and G. Borah, Eur. J. Org. Chem. 2017, 2017, 2272.
13 (a) S. R. Patpi, L. Pulipati, P. Yogeeswari, D. Sriram, N. Jain,
B. Sridhar, R. Murthy, A. DeviT, S. V. Kalivendi and S. Kantevari,
J. Med. Chem. 2012, 55, 3911; (b) V. Butsch, F. Bꢀrgel, F. Galla,
K. Schwegmann, S. Hermann, M. Schꢁfers, B. Riemann, B.
Wꢂnsch and S. Wagner, J. Med. Chem. 2018, 61, 4115.
14 A. R. K. Antonio J. Martínez-Martínez, Robert E. Mulvey
and Charles T. O'Hara, Science, 2014, 346, 834.
15 The supplementary crystallographic data for 3ja (CCDC
1974735), 3ma (CDCC 1974732), 3na (CDCC 1974734), 3oa
(CDCC 1974733) can be obtained free of charge from the
Cambridge Crystallographic Data Center.
2
(a) L. Schulz, M. Enders, B. Elsler, D. Schollmeyer, K. M.
Dyballa, R. Franke and S. R. Waldvogel, Angew. Chem. Int. Ed.
2017, 56, 4877; (b) C. Mei and W. Lu, J. Org. Chem. 2018, 83,
4812; (c) Y. Shi, J. Liu, Y. Yang and J. You, Chem. Commun. 2019,
4 | J. Name., 2019, 00, 1-3
This journal is © The Royal Society of Chemistry 20xx
Please do not adjust margins