ChemComm
Page 4 of 5
Int. Ed., 2009, 48, 5094; (b) O. Daugulis, H.-Q. Do and D.
Angew. Chem. Int. Ed., 2015, 54, 8515; (c) T. Patra, S. Bag, R.
Shabashov, Acc. Chem. Res., 2009, 42, 1074; (c) L. Ackermann,
Chem. Commun., 2010, 46, 4866; (d) T. W. Lyons and M. S. Sanford,
Chem. Rev., 2010, 110, 1147; (e) D. A. Colby, R. G. Bergman and J.
A. Ellman, Chem. Rev., 2010, 110, 624; (f) J. Wencel-Delord, T.
Dröge, F. Liu and F. Glorius, Chem. Soc. Rev., 2011, 40, 4740; (g) G.
Song, F. Wang and X. Li, Chem. Soc. Rev., 2012, 41, 3651; (h) G.
Rouquet and N. Chatani, Angew. Chem. Int. Ed., 2013, 52, 11726; (i)
M. Zhang, Y. Zhang, X. Jie, H. Zhao, G. Li and W. Su, Org. Chem.
Front., 2014, 1, 843; (j) Z. Chen, B. Wang, J. Zhang, W. Yu, Z. Liu
and Y. Zhang, Org. Chem. Front., 2015, 2, 1107.
Kancherla, A. Mondal, A. Dey, S. Pimparkar, S. Agasti, A. Modak
DOI: 10.1039/C7CC00110J
Bhaskararao, S. Singha, R. B. Sunoj and D. Maiti, Chem. Sci., 2016,
7, 3147. (e) Y. Kuninobu, H. Ida, M. Nishi and M. Kanai, Nat.
Chem., 2015, 7, 712; For examples on para-selective C–H
functionalization, see: (f) S. Bag, T. Patra, A. Modak, A. Deb, S.
Maity, U. Dutta, A. Dey, R. Kancherla, A. Maji, A. Hazra, M. Bera
and D. Maiti, J. Am. Chem. Soc., 2015, 137, 11888; (g) T. Patra, S.
Bag, R. Kancherla, A. Mondal, A. Dey, S. Pimparkar, S. Agasti, A.
Modak and D. Maiti, Angew. Chem. Int. Ed., 2016, 55, 7751.
75
80
5
10
15
20
25
2
3
(a) A. Dey, S. Agasti and D. Maiti, Org. Biomol. Chem., 2016, 14,
5440; (b) J. Yang, Org. Biomol. Chem., 2015, 13, 1930; (c) J. Ye and
M. Lautens, Nat. Chem., 2015, 7, 863; (d) J. Li, S. D. Sarkar and L.
Ackermann, Top. Organomet. Chem., 2016, 55, 217.
10 (a) S. Li, H. Ji, L. Cai and G. Li, Chem. Sci., 2015, 6, 5595; (b) S.
Li , L. Cai, H. Ji, L. Yang and G. Li, Nat. Commun., 2015, 7, 10443.
85 11 X.-C. Wang, W. Gong, L.-Z. Fang, R.-Y. Zhu, S. Li, K. M. Engle
and J.-Q. Yu, Nature, 2015, 519, 334.
12 For selected reviews on Catellani reaction, see: (a) M. Catellani, Top.
Organomet. Chem., 2005, 14, 21; (b) M. Catellani, E. Motti and N.
Della Ca’, Acc. Chem. Res., 2008, 41, 1512; (c) A. Martins, B.
For examples on steric- or electronic-controlled meta-selective C–H
functionalization, see: (a) J.-Y. Cho, M. K. Tse, D. Holmes, R. E.
Maleczka Jr. and M. R. Smith III, Science, 2002, 295, 305; (b) T.
Ishiyama, J. Takagi, K. Ishida, N. Miyaura, N. R. Anastasi and J. F.
Hartwig, J. Am. Chem. Soc., 2002, 124, 390; (c) J. M. Murphy, X.
Liao and J. F. Hartwig, J. Am. Chem. Soc., 2007, 129, 15434; (d) C.
Cheng and J. F. Hartwig, Science, 2014, 343, 853; (e) Y.-H. Zhang,
B.-F. Shi and J.-Q Yu, J. Am. Chem. Soc., 2009, 131, 5072; (f) M. Ye,
G.-L. Gao and J.-Q. Yu, J. Am. Chem. Soc., 2011, 133, 6964; (g) M.
Ye, G.-L. Gao, A. J. F. Edmunds, P. A. Worthington, J. A. Morris and
J.-Q. Yu, J. Am. Chem. Soc., 2011, 133, 19090; (h) H. J. Davis, M. T.
Mihai and R. J. Phipps, J. Am. Chem. Soc., 2016, 138, 12759; For a
review, see: (i) I. A. I. Mkhalid, J. H. Barnard, T. B. Marder, J. M.
Murphy and J. F. Hartwig, Chem. Rev., 2010, 110, 890.
For examples on diaryliodonium salt-mediated meta-arylation, see:
(a) R. J. Phipps and M. J. Gaunt, Science, 2009, 323, 1593; (b) H. A.
Duong, R. E. Gilligan, M. L. Cooke, R. J. Phipps and M. J. Gaunt,
Angew. Chem. Int. Ed., 2011, 50, 463; (c) Y. Yang, R. Li, Y. Zhao, D.
Zhao and Z. Shi, J. Am. Chem. Soc., 2016, 138, 8734.
For examples on traceless directing group strategy, see: (a) J.
Cornella, M. Righi and I. Larrosa, Angew. Chem. Int. Ed., 2011, 50,
9429; (b) J. Luo, S. Preciado and I. Larrosa, J. Am. Chem. Soc.,
2014, 136, 4109; (c) Y. Zhang, H. Zhao, M. Zhang and W. Su,
90
95
Mariampillai and M. Lautens, Top. Curr. chem., 2010, 292, 1; (d) N.
Della Ca’, M. Fontana, E. Motti and M. Catellani, Acc. Chem. Res.
2016, 49, 1389.
13 Z. Dong, J. Wang and G. Dong, J. Am. Chem. Soc., 2015, 137, 5887.
14 (a) P.-X. Shen, X.-C. Wang, P. Wang, R.-Y. Zhu and J.-Q. Yu, J. Am.
Chem. Soc., 2015, 137, 11574; (b) P. Wang, M. E. Farmer, X. Huo, P.
Jain, P.-X. Shen, M.Ishoey, J. E. Bradner, S. R. Wisniewski, M. D.
Eastgate and J.-Q. Yu, J. Am. Chem. Soc., 2016, 138, 9269; (c) P.
Wang, G.-C. Li, P. Jain, M. E. Farmer, J. He, P.-X. Shen and J.-Q. Yu,
J. Am. Chem. Soc., 2016, 138, 14092.
100 15 J. Han, L. Zhang, Y. Zhu, Y. Zheng, X. Chen, Z.-B. Huang, D.-Q.
Shi and Y. Zhao, Chem. Commun., 2016, 52, 6903.
30 4
35 5
40
16 During the submission of this manuscript, Maiti reported a Pd-
catalyzed interannular meta-olefination of biaryl compounds using
2-cyano benzoic acid as a well-defined template. See: (a) S. Maity,
105
E. Hoque, U. Dhawa and D. Maiti, Chem. Commun., 2016, 52,
14003; Yu reported ligand-enabled meta-selective C–H arylation of
nosyl-protected 2-aryl anilines. See: (b) Q. Ding, S. Ye, G. Cheng, P.
Wang, M. E. Farmer and J.-Q. Yu, J. Am. Chem. Soc., DOI:
10.1021/jacs.6b11097.
Angew. Chem. Int. Ed., 2015, 54, 3817; (d) X.-Y. Shi, K.-Y. Liu, J. 110 17 (a) J.-W. Xu, Z.-Z. Zhang, W.-H. Rao and B.-F. Shi, J. Am. Chem.
Fan, X.-F. Dong, J.-F. Wei and C.-J. Li, Chem. Eur. J., 2015, 21,
1900; (e) N. Y. P. Kumar, A. Bechtoldt, K. Raghuvanshi and L.
Ackermann, Angew. Chem. Int. Ed., 2016, 55, 6929. (f) R. Bisht and
B. Chattopadhyay, J. Am. Chem. Soc., 2016, 138, 84.
Soc., 2016, 138, 10750; (b) Y.-J. Liu, Y.-H. Liu, Z.-Z. Zhang, S.-Y.
Yan, K. Chen and B.-F. Shi, Angew. Chem. Int. Ed., 2016, 55, 13859.
18 (a) W. C. P. Tsang, N. Zheng and S. L. Buchwald, J. Am. Chem. Soc.,
2005, 127, 14560; (b) W. C. P. Tsang, R. H. Munday, G. Brasche, N.
Zheng and S. L. Buchwald, J. Org. Chem., 2008, 73, 7603; (c) Y.
Wang and Q. Zhu, Adv. Synth. Catal., 2012, 354, 1902.
19 For selected examples, see: (a) Z. Liang, L. Ju, Y. Xie, L. Huang and
Y. Zhang, Chem. Eur. J., 2012, 18, 15816; (b) Z. Liang, R. Feng, H.
Yin and Y. Zhang, Org. Lett., 2013, 15, 4544; (c) D. Liang, Z. Hu, J.
Peng, J. Huang and Q. Zhu, Chem. Commun., 2013, 49, 173.
20 (a) M. Miura, T. Tsuda, T. Satoh, S. Pivsa-Art and M. Nomura, J.
Org. Chem., 1998, 63, 5211; (b) B. S. Kim, S. Y. Lee and S. W.
Youn, Chem. Asian J., 2011, 6, 1952; (c) Y.-Y. Liu, R.-J. Song, C.-Y.
Wu, L.-B. Gong, M. Hu, Z.-Q. Wang, Y.-X. Xie and J.-H. Li, Adv.
Synth. Catal., 2012, 354, 347.
21 (a) M. Wasa, K. S. L. Chan, X.-G. Zhang, J. He, M. Miura and J.-Q.
Yu, J. Am. Chem. Soc., 2012, 134, 18570; (b) R.-Y. Zhu, J. He, X.-C.
Wang and J.-Q. Yu, J. Am. Chem. Soc., 2014, 136, 13194; (c) J. He,
S. Li, Y. Deng, H. Fu, B. N. Laforteza, J. E. Spangler, A. Homs and
J.-Q. Yu, Science, 2014, 343, 1216; (d) G. Chen, T. Shigenari, P. Jain,
Z. Zhang, Z. Jin, J. He, S. Li, C. Mapelli, M. M. Miller, M. A. Poss,
P. M. Scola, K.-S. Yeung and J.-Q. Yu, J. Am. Chem. Soc., 2015, 137,
3338; (e) D. Zhu, G. Yang, J. He, L. Chu, G. Chen, W. Gong, K.
Chen, M. D. Eastgate and J.-Q. Yu, Angew. Chem. Int. Ed., 2015, 54,
2497.
6
(a) O. Saidi, J. Marafie, A. E. W. Ledger, P. M. Liu, M. F. Mahon, G. 115
Kociok-Köhn, M. K. Whittlesey and C. G. Frost, J. Am. Chem. Soc.,
2011, 133, 19298; (b) L. Ackermann, N. Hofmann and R. Vicente,
Org. Lett., 2011, 13, 1875. (c) N. Hofmann and L. Ackermann, J.
Am. Chem. Soc., 2013, 135, 5877; (d) J. Li, S. Warratz, D. Zell, S. D.
Sarkar, E. E. Ishikawa and L. Ackermann, J. Am. Chem. Soc., 2015, 120
137, 13894; (e) C. J. Teskey, A. Y. W. Lui and M. F. Greaney, Angew.
Chem. Int. Ed., 2015, 54, 11677; (f) Q. Yu, L. Hu, Y. Wang, S.
Zheng and J. Huang, Angew. Chem. Int. Ed., 2015, 54, 15284; (g) Z.
Fan, J. Ni and A. Zhang, J. Am. Chem. Soc., 2016, 138, 8470. (h) S.
Warratz, D. J. Burns, C. Zhu, K. Korvorapun, T. Rogge, J. Scholz, C. 125
Jooss, D. Gelman, and L. Ackermann, Angew. Chem. Int. Ed., 2017,
56, DOI: 10.1002/anie.201609014; For example of Ru(II)-catalyzed
para-selective C–H functionalization, see: (i) W. Liu and L.
Ackermann, Org. Lett., 2013, 15, 3484.
(a) D. Leow, G. Li, T.-S. Mei and J.-Q. Yu, Nature, 2012, 486, 518; 130
(b) H.-X. Dai, G. Li, X.-G. Zhang, A. F. Stepan and J.-Q. Yu, J. Am.
Chem. Soc., 2013, 135, 7567; (c) L. Wan, N. Dastbaravardeh, G. Li
and J.-Q. Yu, J. Am. Chem. Soc., 2013, 135, 18056; (d) G. Yang, P.
Lindovska, D. Zhu, J. Kim, P. Wang, R.-Y. Tang, M. Movassaghi
and J.-Q. Yu, J. Am. Chem. Soc., 2014, 136, 10807; (e) R.-Y. Tang, 135
G. Li and J.-Q. Yu, Nature, 2014, 507, 215; (f) Y. Deng and J.-Q. Yu,
Angew. Chem. Int. Ed., 2015, 54, 888. (g) L. Chu, M. Shang, K.
Tanaka, Q. Chen, N. Pissarnitski, E. Streckfuss and J.-Q. Yu, ACS
Cent. Sci., 2015, 1, 394.
45
50
55
7
60
65
22 X.-F. Wu, H. Neumann and M. Beller, Chem. Commun., 2011, 47,
7959.
23 C. Tang and N. Jiao, J. Am. Chem. Soc., 2012, 134, 18924.
24 (a) M. Jung and S. W. Youn, Bull. Korean Chem. Soc., 2011, 32,
2865; (b) O. Daugulis and V. G. Zaitsev, Angew. Chem. Int. Ed.,
2005, 44, 4046; (c) B. S. Kim, C. Jang, D. J. Lee and S. W. Youn,
Chem. Asian J., 2010, 5, 2336.
8
S. Lee, H. Lee and K. L. Tan, J. Am. Chem. Soc., 2013, 135, 18778.
(a) M. Bera, A. Modak, T. Patra, A. Maji and D. Maiti, Org. Lett.,
2014, 16, 5760; (b) M. Bera, A. Maji, S. K. Sahoo and D. Maiti,
140
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