Organic Letters
Letter
Li, L.-B.; Wang, A.-Zh.; Huang, H.-W. Org. Lett. 2011, 13, 1028.
(h) Feng, X.; Du, H. Youji Huaxue 2015, 35, 259.
(2) Kasak, P.; Arion, B.; Widhalm, M. Tetrahedron: Asymmetry 2006,
17, 3084.
2015, 34, 4618. (w) Zhang, F.-L.; Hong, K.; Li, T.-J.; Park, H.; Yu, J.-Q.
Science 2016, 351, 252.
(12) For selected examples of enantioselective palladium(II)-catalyzed
C−H activation/C−Xbond formation, see: (a) Cheng, X.-F.; Li, Y.; Su,
Y.-M.; Yin, F.; Wang, J.-Y.; Sheng, J.; Vora, H. U.; Wang, X.-S.; Yu, J.-Q. J.
Am. Chem. Soc. 2013, 135, 1236. (b) Chu, L.; Wang, X.-C.; Moore, C. E.;
Rheingold, A. L.; Yu, J.-Q. J. Am. Chem. Soc. 2013, 135, 16344. (c) Chu,
L.; Xiao, K.-J.; Yu, J.-Q. Science 2014, 346, 451. (d) Gao, D.-W.; Gu, Q.;
You, S.- L. ACS Catal. 2014, 4, 2741.
(13) For selected examples of transition-metal-catalyzed C−H
activation of organophosphorus compounds, see: (a) Kuninobu, Y.;
Yoshida, T.; Takai, K. J. Org. Chem. 2011, 76, 7370. (b) Baba, K.; Tobisu,
M.; Chatani, N. Angew. Chem., Int. Ed. 2013, 52, 11892. (c) Chan, L. Y.;
Kim, S.; Ryu, T.; Lee, P. H. Chem. Commun. 2013, 49, 4682. (d) Wang,
H.-L.; Hu, R.-B.; Zhang, H.; Zhou, A.-X.; Yang, S.-D. Org. Lett. 2013, 15,
5302. (e) Feng, C.-G.; Ye, M.; Xiao, K.-J.; Li, S.; Yu, J.-Q. J. Am. Chem.
Soc. 2013, 135, 9322. (f) Li, C.; Yano, T.; Ishida, N.; Murakami, M.
Angew. Chem., Int. Ed. 2013, 52, 9801. (g) Unoh, Y.; Hashimoto, Y.;
Takeda, D.; Hirano, K.; Satoh, T.; Miura, M. Org. Lett. 2013, 15, 3258.
(h) Ryu, T.; Kim, J.; Park, Y.; Kim, S.; Lee, P. H. Org. Lett. 2013, 15,
3986. (i) Zhao, D.; Nimphius, C.; Lindale, M.; Glorius, F. Org. Lett.
2013, 15, 4504. (j) Chen, Y.-R.; Duan, W.-L. J. Am. Chem. Soc. 2013,
135, 16754. (k) Gwon, D.; Lee, D.; Kim, J.; Park, S.; Chang, S. Chem. -
Eur. J. 2014, 20, 12421. (l) Chen, Y.-R.; Duan, W.-L. Synthesis 2014, 46,
1067.
(14) For selected examples of transition-metal-catalyzed enantiose-
lective C−H activation to synthesize chiral phosphrous compounds, see:
(a) Sun, Y.; Cramer, N. Angew. Chem., Int. Ed. 2017, 56, 364. (b) Lin, Z.-
Q.; Wang, W.-Z.; Yan, S.-B.; Duan, W.-L. Angew. Chem., Int. Ed. 2015,
54, 6265. (c) Liu, L.; Zhang, A.-A.; Wang, Y.; Zhang, F.; Zuo, Z.; Zhao,
W.-X.; Feng, C.-L.; Ma, W. Org. Lett. 2015, 17, 2046. (d) Du, Z.-J.; Guan,
J.; Wu, G.-J.; Xu, P.; Gao, L.-X.; Han, F.-S. J. Am. Chem. Soc. 2015, 137,
632. (e) Guan, J.; Wu, G.-J.; Han, F.-S. Chem. - Eur. J. 2014, 20, 3301.
(f) Gwon, D.; Lee, D.; Kim, J.; Park, S.; Chang, S. Chem. - Eur. J. 2014,
20, 12421.
(3) (a) Defieber, C.; Ariger, M. A.; Moriel, P.; Carreira, E. M. Angew.
Chem., Int. Ed. 2007, 46, 3139. (b) Mariz, R.; Bricen
Organometallics 2008, 27, 6605.
̌
o, A.; Dorta, R.
(4) (a) Cao, Z.; Liu, Y.; Liu, Z.; Feng, X.; Zhuang, M.; Du, H.-F. Org.
Lett. 2011, 13, 2164. (b) Liu, Z.; Cao, Z.; Du, H.-F. Org. Biomol. Chem.
2011, 9, 5369.
(5) Yu, Y.-N.; Xu, M.-H. Org. Chem. Front. 2014, 1, 738.
(6) Feng, J.; Li, B.; He, Y.; Gu, Z. Angew. Chem., Int. Ed. 2016, 55, 2186.
(7) For selected reviews on C−H bond activations, see: (a) Kakiuchi,
F.; Murai, S. Acc. Chem. Res. 2002, 35, 826. (b) Li, B.; Yang, S.; Shi, Z.
Synlett 2008, 2008, 949. (c) Chen, X.; Engle, K. M.; Wang, D.-H.; Yu, J.-
Q. Angew. Chem., Int. Ed. 2009, 48, 5094. (d) Lyons, T. W.; Sanford, M.
S. Chem. Rev. 2010, 110, 1147. (e) Ackermann, L. Chem. Rev. 2011, 111,
1315. (f) Kuhl, N.; Hopkinson, M. N.; Wencel-Delord, J.; Glorius, F.
Angew. Chem., Int. Ed. 2012, 51, 10236. (g) Song, G.; Wang, F.; Li, X.
Chem. Soc. Rev. 2012, 41, 3651.
(8) For reviews on enantioselective C−H activations, see: (a) Wencel-
Delord, J.; Colobert, W. F. Chem. - Eur. J. 2013, 19, 14010. (b) Engle, K.
M.; Yu, J.-Q. J. Org. Chem. 2013, 78, 8927. (c) Zheng, C.; You, S.-L. RSC
Adv. 2014, 4, 6173.
(9) For selected examples of enantioselective ruthenium- and
rhodium-catalyzed C−H activation, see: (a) Milczek, E.; Boudet, N.;
Blakey, S. Angew. Chem., Int. Ed. 2008, 47, 6825. (b) Tran, D. N.;
Cramer, N. Angew. Chem., Int. Ed. 2010, 49, 8181. (c) Hyster, T. K.;
Knorr, L.; Ward, T. R.; Rovis, T. Science 2012, 338, 500. (d) Ye, B.;
Cramer, N. Science 2012, 338, 504. (e) Kuninobu, Y.; Yamauchi, K.;
Tamura, N.; Seiki, T.; Takai, K. Angew. Chem., Int. Ed. 2013, 52, 1520.
(f) Ye, B.; Cramer, N. J. Am. Chem. Soc. 2013, 135, 636. (g) Tran, D. N.;
Cramer, N. Angew. Chem., Int. Ed. 2013, 52, 10630. (h) Ye, B.; Donets, P.
A.; Cramer, N. Angew. Chem., Int. Ed. 2014, 53, 507. (i) Ye, B.; Cramer,
N. Angew. Chem., Int. Ed. 2014, 53, 7896.
(10) For selected examples of iridium-catalyzed enantioselective C−H
activation, see: (a) Pan, S.; Endo, K.; Shibata, T. Org. Lett. 2011, 13,
4692. (b) Sevov, C. S.; Hartwig, J. F. J. Am. Chem. Soc. 2013, 135, 2116.
(c) Nishimura, T.; Ebe, M.; Nagamoto, Y.; Hayashi, T. Chem. Sci. 2013,
4, 4499. (d) Shibata, T.; Shizuno, T. Angew. Chem., Int. Ed. 2014, 53,
5410.
(15) Shi, B.-F.; Zhang, Y.-H.; Lam, J. K.; Wang, D.-H.; Yu, J.-Q. J. Am.
Chem. Soc. 2010, 132, 460.
(16) Xiao, K.-J.; Chu, L.; Yu, J.-Q. Angew. Chem., Int. Ed. 2016, 55,
2856.
(17) (a) Zheng, J.; You, S.-L. Angew. Chem., Int. Ed. 2014, 53, 13244.
(b) Zheng, J.; Cui, W.-J.; Zheng, C.; You, S.-L. J. Am. Chem. Soc. 2016,
138, 5242.
(18) (a) Wesch, T.; Leroux, F. R.; Colobert, F. Adv. Synth. Catal. 2013,
355, 2139. (b) Hazra, C. K.; Dherbassy, Q.; Wencel-Delord, J.; Colobert,
F. Angew. Chem., Int. Ed. 2014, 53, 13871. (c) Dherbassy, Q.; Schwertz,
G.; Chesse, M.; Hazra, C. K.; Wencel-Delord, J.; Colobert, F. Chem. -
Eur. J. 2016, 22, 1735.
(11) For selected examples of enantioselective Pd-catalyzed C−H
activation/C−C bond formation, see: (a) Mikami, K.; Hatano, M.;
Terada, M. Chem. Lett. 1999, 28, 55. (b) Shi, B.-F.; Maugel, N.; Zhang, Y.
H.; Yu, J.-Q. Angew. Chem., Int. Ed. 2008, 47, 4882. (c) Albicker, M. R.;
Cramer, N. Angew. Chem., Int. Ed. 2009, 48, 9139. (d) Renaudat, A.;
Jean-Gerard, L.; Jazzar, R.; Kefalidis, C. E.; Clot, E.; Baudoin, O. Angew.
Chem., Int. Ed. 2010, 49, 7261. (e) Anas, S.; Cordi, A.; Kagan, H. B.
Chem. Commun. 2011, 47, 11483. (f) Nakanishi, M.; Katayev, D.;
(19) (a) Ma, Y.-N.; Zhang, H.-Y.; Yang, S.-D. Org. Lett. 2015, 17, 2034.
(b) Ma, Y.-N.; Yang, S.-D. Chem. Rec. 2016, 16, 977.
(20) (a) Giri, R.; Shi, B. F.; Engle, K. M.; Maugel, N.; Yu, J.-Q. Chem.
Soc. Rev. 2009, 38, 3242. (b) Davies, H. M. L.; Du Bois, J.; Yu, J.-Q.
Chem. Soc. Rev. 2011, 40, 1855. (c) Engle, K. M.; Mei, T.-S.; Wasa, M.;
Yu, J.-Q. Acc. Chem. Res. 2012, 45, 788. (d) Xiao, K.-J.; Chu, L.; Chen,
G.; Yu, J.-Q. J. Am. Chem. Soc. 2016, 138, 7796. (e) Cheng, G.-J.; Chen,
P.; Sun, T.-Y.; Zhang, X.; Yu, J.-Q.; Wu, Y.-D. Chem. - Eur. J. 2015, 21,
11180.
(21) (a) Gao, D.-W.; Shi, Y.-C.; Gu, Q.; Zhao, Z.-L.; You, S.-L. J. Am.
Chem. Soc. 2013, 135, 86. (b) Gao, D.-W.; Gu, Q.; You, S.-L. J. Am.
Chem. Soc. 2016, 138, 2544.
(22) (a) Xie, J.-H.; Zhu, S.-F.; Fu, Y.; Hu, A.-G.; Zhou, Q.-L. Pure Appl.
Chem. 2005, 77, 2121. (b) Minnaard, A. J.; Feringa, B. L.; Lefort, L.; de
Vries, J. G. Acc. Chem. Res. 2007, 40, 1267. (c) Eberhardt, L.; Armspach,
D.; Harrowfield, J.; Matt, D. Chem. Soc. Rev. 2008, 37, 839. (d) Martin,
R.; Buchwald, S. L. Acc. Chem. Res. 2008, 41, 1461.
Besnard, C.; Kundig, E. P. Angew. Chem., Int. Ed. 2011, 50, 7438.
̈
(g) Wasa, M.; Engle, K. M.; Lin, D. W.; Yoo, E. J.; Yu, J.-Q. J. Am. Chem.
Soc. 2011, 133, 19598. (i) Martin, N.; Pierre, C.; Davi, M.; Jazzar, R.;
Baudoin, O. Chem. - Eur. J. 2012, 18, 4480. (j) Larionov, E.; Nakanishi,
M.; Katayev, D.; Besnard, C.; Kundig, E. P. Chem. Sci. 2013, 4, 1995.
̈
(k) Pi, C.; Li, Y.; Cui, X.; Zhang, H.; Han, Y.; Wu, Y. Chem. Sci. 2013, 4,
2675. (l) Xiao, K.-J.; Lin, D. W.; Miura, M.; Zhu, R.-Y.; Gong, W.; Wasa,
M.; Yu, J.-Q. J. Am. Chem. Soc. 2014, 136, 8138. (m) Pi, C.; Cui, X.; Liu,
X.; Guo, M.; Zhang, H.; Wu, Y. Org. Lett. 2014, 16, 5164. (n) Liu, L.;
Zhang, A.-A.; Zhao, R.-J.; Li, F.; Meng, T.-J.; Ishida, N.; Murakami, M.;
Zhao, W.-X. Org. Lett. 2014, 16, 5336. (o) Gao, D.-W.; Yin, Q.; Gu, Q.;
You, S.-L. J. Am. Chem. Soc. 2014, 136, 4841. (p) Deng, R.; Huang, Y.;
Ma, X.; Li, G.; Zhu, R.; Wang, B.; Kang, Y.-B.; Gu, Z. J. Am. Chem. Soc.
2014, 136, 4472. (q) Xiao, K.-J.; Lin, D.; Miura, M.; Zhu, R.-Y.; Gong,
W.; Wasa, M.; Yu, J.-Q. J. Am. Chem. Soc. 2014, 136, 8138. (r) Pedroni,
J.; Boghi, M.; Saget, T.; Cramer, N. Angew. Chem., Int. Ed. 2014, 53,
9064. (s) Chan, K. S. L.; Fu, H.; Yu, J.-Q. J. Am. Chem. Soc. 2015, 137,
2042. (t) Yan, S.-B.; Zhang, S.; Duan, W.-L. Org. Lett. 2015, 17, 2458.
(u) Laforteza, B. N.; Chan, K. S. L.; Yu, J.-Q. Angew. Chem., Int. Ed. 2015,
54, 11143. (v) Gao, D.-W.; Zheng, C.; Gu, Q.; You, S.-L. Organometallics
D
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