Angewandte Chemie International Edition
10.1002/anie.201915624
RESEARCH ARTICLE
We gratefully acknowledge The Scripps Research Institute
[7]
a) G.-J. Cheng, Y.-F. Yang, P. Liu, P. Chen, T.-Y. Sun, G. Li, X. Zhang,
K. N. Houk, J.-Q. Yu, Y.-D. Wu, J. Am. Chem. Soc. 2014, 136, 894; b)
Y.-F. Yang, G.-J. Cheng, P. Liu, D. Leow, T. Y. Sun, P. Chen, X. Zhang,
J.-Q. Yu, Y.-D. Wu, K. N. Houk, J. Am. Chem. Soc. 2014, 136, 344; c) L.
Fang, T. G. Saint-Denis, B. L. H. Taylor, S. Ahlquist, K. Hong, S. Liu, L.
Han, K. N. Houk, J.-Q. Yu, J. Am. Chem. Soc. 2017, 139, 10702; d) Y.-
F. Yang, X. Hong, J.-Q. Yu, K. N. Houk, Acc. Chem. Res. 2017, 50,
2853.
(
TSRI), the NIH (National Institute of General Medical Sciences
grant R01 GM102265) and Bristol-Myers Squibb for financial
support. We gratefully acknowledge Dr. Jason Chen (TSRI),
Brittany Sanchez (TSRI), and Emily Sturgell (TSRI) for HRMS
analysis. This work was also supported by the National Science
Foundation (CHE-1764320 to KNH) and the National Science
Foundation under the CCI Center for Selective C–H
[8]
For examples of pyridine or quinolone ligand promoted C–H activation,
see: a) J. He, S. Li, Y. Deng, H. Fu, B. N. Laforteza, J. E. Spangler, A.
Homs, J.-Q. Yu, Science 2014, 343, 1216. b) S. Li, G. Chen, C.-G.
Feng, W. Gong, J.-Q. Yu, J. Am. Chem. Soc. 2014, 136, 5267; c) S. Li,
R.-Y. Zhu, K.-J. Xiao, J.-Q. Yu, Angew. Chem. Int. Ed. 2016, 55, 4317;
Angew. Chem. 2016, 128, 4389; d) H. Park, N. Chekshin, P.-X. Shen,
J.-Q. Yu, ACS Catal. 2018, 8, 9292.
Functionalization
(CHE-1700982).
Computations
were
performed on the Hoffman2 cluster at UCLA and the Extreme
Science and Engineering Discovery Environment (XSEDE),
which is supported by the NSF (OCI-1053575). K. L. B. thanks
the Saul Winstein Fellowship (UCLA) for support.
[
[
9]
a) P.-X. Shen, L. Hu, Q. Shao, K. Hong, J.-Q. Yu, J. Am. Chem. Soc.
2
018, 140, 6545; b) Z. Zhuang, C.-B. Yu, G. Chen, Q.-F. Wu, Y. Hsiao,
C. L. Joe, J. X. Qiao, M. A. Poss, J.-Q. Yu, J. Am. Chem. Soc. 2018,
40, 10363.
Conflict of interest
1
10] For examples of 2-pyridone ligand promoted C–H activation, see: a) P.
Wang, M. E. Farmer, X. Huo, P. Jain, P.-X. Shen, M. Ishoey, J. E.
Bradner, S. R. Wisniewski, M. D. Eastgate, J.-Q. Yu, J. Am. Chem. Soc.
The authors declare no conflict of interest.
2
016, 138, 9269; b) P. Wang, P. Verma, G. Xia, J. Shi, J. X. Qiao, S.
Keywords: biphenyl • C–H activation • remote • pyridone • Pd–
Tao, P. T. W. Cheng, M. A. Poss, M. E. Farmer, K.-S. Yeung, J.-Q. Yu,
Nature 2017, 551, 489; c) Y.-Q. Chen, Z. Wang, Y. Wu, S. R.
Wisniewski, J. X. Qiao, W. R. Ewing, M. D. Eastgate, J.-Q. Yu, J. Am.
Chem. Soc. 2018, 140, 17884; d) R.-Y. Zhu, Z.-Q. Li, H. S. Park, C. H.
Senanayake, J.-Q. Yu, J. Am. Chem. Soc. 2018, 140, 3564.
Ag dimer
[
[
1]
2]
a) R. Breslow, M. A. Winnik, J. Am. Chem. Soc. 1969, 91, 3083; b) R.
Breslow, R. J. Corcoran, B. B. Snider, J. Am. Chem. Soc. 1974, 96,
6791; c) R. Breslow, Acc. Chem. Res. 1980, 13, 170.
[
[
[
11] T. Mavromoustakos, G. Agelis, S. Durdagi, Expert Opin. Ther. Pat.
For other examples of site-selective C–H activation, see: a) Y.-H.
Zhang, B.-F. Shi, J.-Q. Yu, J. Am. Chem. Soc. 2009, 131, 5072; b) C.
Cheng, J. F. Hartwig, Science 2014, 343, 853; c) R. J. Phipps, M. J.
Gaunt, Science 2009, 323, 1593; d) Y. Yang, R. Li, Y. Zhao, D. Zhao, Z.
Shi, J. Am. Chem. Soc. 2016, 138, 8734; e) Y. Kuninobu, H. Ida, M.
Nishi, M. Kanai, Nat. Chem. 2015, 7, 712; f) H. J. Davis, M. T. Mihai, R.
J. Phipps, J. Am. Chem. Soc. 2016, 138, 12759; g) X.-C. Wang, W.
Gong, L.-Z. Fang, R.-Y. Zhu, S. Li, K. M. Engle, J.-Q. Yu, Nature 2015,
2013, 23, 1483.
12] E. M. Simmons, J. F. Hartwig, Angew. Chem. Int. Ed. 2012, 51, 3066;
Angew. Chem. 2012, 124, 3120.
13] M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb,
J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A.
Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F.
Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K.
Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O.
Kitao, H. Nakai, T. Vreven, J. A. Montgomery, J. E. Peralta, F. Ogliaro,
M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, R.
Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S.
S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E.
Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.
E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W.
Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P.
Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, Ö. Farkas; J. B.
Foresman, J. V. Ortiz, J. Cioslowski, D. J. Fox, Gaussian 09; Gaussian
Inc.: Wallingford, CT, 2009.
519, 334; h) Z. Dong, J. Wang, G. Dong, J. Am. Chem. Soc. 2015, 137,
5887; i) O. Saidi, J. Marafie, A. E. Ledger, P. M. Liu, M. F. Mahon, G.
Kociok-Köhn, M. K. Whittlesey, C. G. Frost, J. Am. Chem. Soc. 2011,
1
33, 19298; j) N. Hofmann, L. Ackermann, J. Am. Chem. Soc. 2013,
35, 5877.
1
[
3]
4]
D. Leow, G. Li, T.-S. Mei, J.-Q. Yu, Nature 2012, 486, 518.
[
For examples of nitrile template-directed meta or para C–H activation,
see: a) H.-X. Dai, G. Li, X.-G. Zhang, A. F. Stepan, J.-Q. Yu, J. Am.
Chem. Soc. 2013, 135, 7567; b) S. Lee, H. Lee, K. L. Tan, J. Am.
Chem. Soc. 2013, 135, 18778; c) L. Wan, N. Dastbaravardeh, G. Li, J.-
Q. Yu, J. Am. Chem. Soc. 2013, 135, 18056; d) R.-Y. Tang, G. Li, J.-Q.
Yu, Nature 2014, 507, 215; e) G. Yang, P. Lindovska, D. Zhu, J. Kim, P.
Wang, R.-Y. Tang, M. Movassaghi, J.-Q. Yu, J. Am. Chem. Soc. 2014,
[
14] a) A. D. Becke, J. Chem. Phys. 1993, 98, 5648; b) C. Lee, W. Yang, R.
G. Parr, Phys. Rev. B: Condens. Matter Mater. Phys. 1988, 37, 785; c)
A. D. Becke, J. Chem. Phys. 1993, 98, 1372; d) P. J. Stephens, F. J.
Devlin, C. F. Chabalowski, M. J. Frisch, J. Phys. Chem. 1994, 98,
136, 10807; f) S. Bag, T. Patra, A. Modak, A. Deb, S. Maity, U. Dutta, A.
Dey, R. Kancherla, A. Maji, A. Hazra, M. Bera, D. Maiti, J. Am. Chem.
Soc. 2015, 137, 11888; g) S. Li, L. Cai, H. Ji, L. Yang, G. Li, Nat.
Commun. 2016, 7, 10443; h) A. Maji, S. Guin, S. Feng, A. Dahiya, V. K.
Singh, P. Liu, D. Maiti, Angew. Chem. Int. Ed. 2017, 56, 14903; Angew.
Chem. 2017, 129, 15099; i) A. Modak, T. Patra, R. Chowdhury, S. Raul,
D. Maiti, Organometallics 2017, 36, 2418; j) L. Zhang, C. Zhao, Y. Liu, J.
Xu, X. Xu, Z. Jin, Angew. Chem. Int. Ed. 2017, 56, 12245; Angew.
Chem. 2017, 129, 12413; k) M. Li, M. Shang, H. Xu, X. Wang, H.-X. Dai,
J.-Q. Yu, Org. Lett. 2019, 21, 540; l) H.-J. Xu, Y.-S. Kang, H. Shi, P.
Zhang, Y.-K. Chen, B. Zhang, Z.-Q. Liu, J. Zhao, W.-Y. Sun, J.-Q. Yu,
Y. Lu, J. Am. Chem. Soc. 2019, 141, 76; m) J. Xu, J. Chen, F. Gao, S.
Xie, X. Xu, Z. Jin, J.-Q. Yu, J. Am. Chem. Soc. 2019, 141, 1903.
1
1623.
[
15] a) R. Ditchfield, W. J. Hehre, J. A. Pople, J. Chem. Phys. 1971, 54, 724;
b) W. J. Hehre, R. Ditchfield, J. A. Pople, J. Chem. Phys. 1972, 56,
2257.
[
16] a) P. J. Hay, W. R. Wadt, J. Chem. Phys. 1985, 82, 299; b) L. E. Roy, P.
J. Hay, R. L. Martin, J. Chem. Theory Comput. 2008, 4, 1029.
[
[
17] Y. Zhao, D. G. Truhlar, Theor. Chem. Acc. 2008, 120, 215.
18] A. V. Marenich, C. J. Cramer, D. G. Truhlar, J. Phys. Chem. B 2009, 113,
6378.
[
[
19] a) M. Dolg, U. Wedig, H. Stoll, H. Preuss, J. Chem. Phys. 1987, 86, 866;
b) D. Andrae, U. Häussermann, M. Dolg, H. Stoll, H. Preuss, Theor.
Chim. Acta 1990, 77, 123.
[
5]
6]
a) M. E. Welsch, S. A. Snyder, B. R. Stockwell, Curr. Opin. Chem. Biol.
20] C. Y. Legault, CYLview, 1.0b; Universitꢀde Sherbrooke, 2009
2010, 14, 347; b) Y.-B. Wang, B. Tan, Acc. Chem. Res. 2018, 51, 534.
(http://www.cylview.org).
[
a) C. W. Liskey, X. Liao, J. F. Hartwig, J. Am. Chem. Soc. 2010, 132,
11389; b) P. Anbarasan, T. Schareina, M. Beller, Chem. Soc. Rev.
2011, 40, 5049.
7
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