Organic Letters
Letter
(20) Lundgren, R. J.; Sappong-Kumankumah, A.; Stradiotto, M. Chem.
- Eur. J. 2010, 16, 1983−1991.
(41) Liu, J.; Chen, G.; Tan, Z. Adv. Synth. Catal. 2016, 358, 1174−
1194.
(21) Schranck, J.; Tlili, A. ACS Catal. 2018, 8, 405−418.
(22) Chan, D. M. T.; Monaco, K. L.; Wang, R.; Winteres, M. P.
Tetrahedron Lett. 1998, 39, 2933−2936.
(42) (a) Tran, L. D.; Roane, J.; Daugulis, O. Angew. Chem., Int. Ed.
2013, 52, 6043−6046. (b) Roane, J.; Daugulis, O. J. Am. Chem. Soc.
2016, 138, 4601−4607. (c) Gandeepan, P.; Muller, T.; Zell, D.; Cera,
G.; Warratz, S.; Ackermann, L. Chem. Rev. 2019, 119, 2192−2452.
(43) Zaitsev, V.; Shabashov, D.; Daugulis, O. J. Am. Chem. Soc. 2005,
127, 13154−13155.
(44) Zhang, Q.; Chen, K.; Rao, W.; Zhang, Y.; Chen, F.-J.; Shi, B.-F.
Angew. Chem., Int. Ed. 2013, 52, 13588−13592.
(45) Yan, S.-Y.; Han, Y.-Q.; Yao, Q.-J.; Nie, X.-L.; Liu, L.; Shi, B.-F.
Angew. Chem., Int. Ed. 2018, 57, 9093−9097.
(46) Tasker, S. Z.; Standley, E. A.; Jamison, T. F. Nature 2014, 509,
299−309.
(47) Lavoie, C. M.; MacQueen, P. M.; Rotta-Loria, N. L.; Sawatzky, R.
S.; Borzenko, A.; Chisholm, A. J.; Hargreaves, B. K. V.; McDonald, R.;
Ferguson, M. J.; Stradiotto, M. Nat. Commun. 2016, 7, 11073.
(48) Lavoie, C. M.; Stradiotto, M. ACS Catal. 2018, 8, 7228−7250.
(49)Borzenko,A.;Rotta-Loria, N.L.;MacQueen, P. M.;Lavoie, C.M.;
McDonald, R.; Stradiotto, M. Angew. Chem., Int. Ed. 2015, 54, 3773−
3777.
(23) Lam, P. Y. S.; Clark, C. G.; Saubern, S.; Adams, J.; Winteres, M. P.;
Chan, D. M. T.; Combs, A. Tetrahedron Lett. 1998, 39, 2941−2944.
(24) Rao, H.;Fu, H.; Jiang, Y.;Zhao, Y. Angew. Chem., Int. Ed. 2009, 48,
1114−1116.
(25) Morofuji, T.; Shimizu, A.; Yoshida, J. J. Am. Chem. Soc. 2013, 135,
5000−5003.
(26) Romero, N. A.; Margrey, K. A.; Tay, N. E.; Nicewicz, D. A. Science
2015, 349, 1326−1330.
(27) Zheng, Y.-W.; Chen, B.; Ye, P.; Feng, K.; Wang, W.; Meng, Q.-Y.;
Wu, L.-Z.; Tung, C.-H. J. Am. Chem. Soc. 2016, 138, 10080−10083.
(28) Paudyal, M. P.; Adebesin, A. M.; Burt, S. R.; Ess, D. H.; Ma, Z.;
Kurti, L.; Falck, J. R. Science 2016, 353, 1144−1147.
̈
(29) For selected reviews on C−H amination, see: (a) Kim, H.; Chang,
S. ACS Catal. 2016, 6, 2341−2351. (b) Zhou, Y.; Yuan, J.; Yang, Q.;
Xiao, Q.; Peng, Y. ChemCatChem 2016, 8, 2178−2192. (c) Park, Y.;
Kim, Y.; Chang, S. Chem. Rev. 2017, 117, 9247−9301.
(50) Zhan, B.-B.; Liu, Y.-H.; Hu, F.; Shi, B.-F. Chem. Commun. 2016,
(30) For selected examples on C−H amination, see: (a) Shuai, Q.;
Deng, G.; Chua, Z.; Bohle, D. S.; Li, C.-J. Adv. Synth. Catal. 2010, 352,
632−636. (b)Tang, R.-J.;Luo, C.-P.;Yang,L.;Li, C.-J. Adv. Synth. Catal.
2013, 355, 869−873. (c) Matsubara, T.; Asako, S.; Ilies, L.; Nakamura,
E. J. Am. Chem. Soc. 2014, 136, 646−649. (d) Shang, M.; Sun, S.-Z.; Dai,
H.-X.; Yu, J.-Q. J. Am. Chem. Soc. 2014, 136, 3354−3357. (e) Peng, J.;
Xie, Z.; Chen, M.; Wang, J.; Zhu, Q. Org. Lett. 2014, 16, 4702−4705.
(f)Peng, J.;Chen, M.;Xie, Z.;Luo, S.;Zhu, Q. Org.Chem. Front. 2014, 1,
777−781. (g) Zhu, D.; Yang, G.; He, J.; Chu, L.; Chen, G.; Gong, W.;
Chen, K.; Eastgate, M. D.; Yu, J.-Q. Angew. Chem., Int. Ed. 2015, 54,
2497−2500. (h) Becker, P.; Pirwerdjan, R.; Bolm, C. Angew. Chem., Int.
Ed. 2015, 54, 15493−15496. (i) Takamatsu, K.; Hirano, K.; Satoh, T.;
Miura, M. J. Org. Chem. 2015, 80, 3242−3249. (j) Sadhu, P.; Alla, S. K.;
Punniyamurthy, T. J. Org. Chem. 2015, 80, 8245−8253. (k) Hermann,
G. N.; Becker, P.; Bolm, C. Angew. Chem., Int. Ed. 2016, 55, 3781−3784.
(l) Mei, R.; Loup, J.; Ackermann, L. ACS Catal. 2016, 6, 793−797.
(m) Kim, H.; Park, G.; Park, J.; Chang, S. ACS Catal. 2016, 6, 5922−
5929. (n) Hu, X.-H.; Yang, X.-F.; Loh, T.-P. ACS Catal. 2016, 6, 5930−
5934. (o) Wang, F.; Wang, H.; Wang, Q.; Yu, S.; Li, X. Org. Lett. 2016,
18, 1306−1309. (p) Zhang, L.-B.; Zhang, S.-K.; Wei, D.; Zhu, X.; Hao,
X.-Q.; Su, J.-H.; Niu, J.-L.; Song, M.-P. Org. Lett. 2016, 18, 1318−1321.
(q) Sadhu, P.; Punniyamurthy, T. Chem. Commun. 2016, 52, 2803−
2806. (r) Pradhan, S.; De, P. B.; Punniyamurthy, T. J. Org. Chem. 2017,
82, 4883−4890. (s) Wang, H.-W.; Lu, Y.; Zhang, B.; He, J.; Xu, H.-J.;
Kang, Y.-S.; Sun, W.-Y.; Yu, J.-Q. Angew. Chem., Int. Ed. 2017, 56, 7449−
7453. (t) Sauermann, N.; Mei, R.; Ackermann, L. Angew. Chem., Int. Ed.
2018, 57, 5090−5094. (u) Zhang, S.-K.;Samanta, R. C.; Sauermann, N.;
Ackermann, L. Chem. - Eur. J. 2018, 24, 19166−19170.
52, 4934−4937.
(51) Yan, Q.; Chen, Z.; Yu, W.; Yin, H.; Liu, Z.; Zhang, Y. Org. Lett.
2015, 17, 2482−2485.
(52) Shiota, H.; Ano, Y.; Aihara, Y.; Fukumoto, Y.; Chatani, N. J. Am.
Chem. Soc. 2011, 133, 14952−14955.
(53) Li, M.; Yang, Y.; Zhou, D.; Wan, D.; You, J. Org. Lett. 2015, 17,
2546−2549.
(54) Uemura, T.; Imoto, S.; Chatani, N. Chem. Lett. 2006, 35, 842−
843.
(55) Castro, L. C. M.; Chatani, N. Chem. Lett. 2015, 44, 410−421.
(56) Wu, X.; Zhao, Y.; Ge, H. J. Am. Chem. Soc. 2014, 136, 1789−1792.
(57) Corcoran, E. B.; Pirnot, M. T.; Lin, S.; Dreher, S. D.; DiRocco, D.
A.;Davies,I.W.;Buchwald,S. L.;MacMillan,D. W.C.Science2016,353,
279−283.
(58) Green, R. A.; Hartwig, J. F. Angew. Chem., Int. Ed. 2015, 54, 3768−
3772.
(31) Tezuka, N.; Shimojo, K.; Hirano, K.; Komagawa, S.; Yoshida, K.;
Wang, C.; Miyamoto, K.; Saito, T.; Takita, R.; Uchiyama, M. J. Am.
Chem. Soc. 2016, 138, 9166−9171.
(32) Li, Z.; Yu, H.; Bolm, C. Angew. Chem., Int. Ed. 2017, 56, 9532−
9535.
(33) Yu, L.; Chen, X.; Liu, D.; Hu, L.; Yu, Y.; Huang, H.; Tan, Z.; Gui,
Q. Adv. Synth. Catal. 2018, 360, 1346−1351.
(34) Xu, L.-L.; Wang, X.; Ma, B.; Yin, M.-X.; Lin, H.-X.; Dai, H.-X.; Yu,
J.-Q. Chem. Sci. 2018, 9, 5160−5164.
(35) Kim, H.; Chang, S. Acc. Chem. Res. 2017, 50, 482−486.
(36) Kikuchi, H.; Yamamoto, K.; Horoiwa, S.; Hirai, S.; Kasahara, R.;
Hariguchi, N.; Matsumoto, M.; Oshima, Y. J. Med. Chem. 2006, 49,
4698−4706.
(37) Liu, X.; Fu, H.; Jiang, Y.; Zhao, Y. Angew. Chem., Int. Ed. 2009, 48,
348−351.
(38) Kim, H.; Heo, J.; Kim, J.; Baik, M.-H.; Chang, S. J. Am. Chem. Soc.
2018, 140, 14350−14356.
(39) Rouquet, G.; Chatani, N. Angew. Chem., Int. Ed. 2013, 52, 11726−
11743.
(40) Rao, W.-H.; Shi, B.-F. Org. Chem. Front. 2016, 3, 1028−1047.
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