Organic Letters
Letter
Adv. Synth. Catal. 2008, 350, 2881. (d) Singh, F. V.; Wirth, T. Org.
Lett. 2011, 13, 6504. (e) Curran, S. P.; Connon, S. J. Org. Lett. 2012,
14, 1074. (f) Tay, D. W.; Tsoi, I. T.; Er, J. C.; Leung, G. Y. C.; Yeung,
Y.-Y. Org. Lett. 2013, 15, 1310. (g) Chen, F.; Tan, C. K.; Yeung, Y.-Y. J.
Am. Chem. Soc. 2013, 135, 1232. (h) Press, D. J.; McNeil, N. M. R.;
Hambrook, M.; Back, T. G. J. Org. Chem. 2014, 79, 9394. (i) Yu, L.; Li,
H.; Zhang, X.; Ye, J.; Liu, J.; Xu, Q.; Lautens, M. Org. Lett. 2014, 16,
1346. (j) Denmark, S. E.; Chi, H. M. J. Am. Chem. Soc. 2014, 136,
8915.
(15) (a) Fukuzawa, S.-i.; Takahashi, K.; Kato, H.; Yamazaki, H. J. Org.
Chem. 1997, 62, 7711. (b) Zhao, L.; Li, Z.; Wirth, T. Eur. J. Org. Chem.
2011, 7080. (c) Back, T. G.; Moussa, Z.; Parvez, M. J. Org. Chem.
2002, 67, 499. (d) Uehlin, L.; Fragale, G.; Wirth, T. Chem.Eur. J.
2002, 8, 1125. (e) Tiecco, M.; Testaferri, L.; Santi, C.; Tomassini, C.;
Marini, F.; Bagnoli, L.; Temperini, A. Angew. Chem., Int. Ed. 2003, 42,
3131.
(16) Balkrishna, S. J.; Prasad, C. D.; Panini, P.; Detty, M. R.; Chopra,
D.; Kumar, S. J. Org. Chem. 2012, 77, 9541.
́
(17) For selected examples, see: (a) Alacid, E.; Najera, C. Eur. J. Org.
Chem. 2008, 3102. (b) Chen, H.; Jiang, H.; Cai, C.; Dong, J.; Fu, W.
Org. Lett. 2011, 13, 992. (c) Liu, J.; Ma, S. Org. Lett. 2013, 15, 5150.
(d) Battistuzzi, G.; Cacchi, S.; Fabrizi, G. Org. Lett. 2003, 5, 777.
(e) Shibuya, M.; Tomizawa, M.; Iwabuchi, Y. J. Org. Chem. 2008, 73,
4750. (f) Li, J.; Tan, C.; Gong, J.; Yang, Z. Org. Lett. 2014, 16, 5370.
ACKNOWLEDGMENTS
■
This work is financially supported by the start-up funding from
Sun Yat-Sen University and a grant from the “One Thousand
Youth Talents” Program of China. We thank Prof. Yiqian Wan
at SYSU for discussion on the configuration determination of
compounds 5.
REFERENCES
■
(1) (a) Ylioja, P. M.; Mosley, A. D.; Charlot, C. E.; Carbery, D. R.
Tetrahedron Lett. 2008, 49, 1111. (b) Harker, W. R. R.; Carswell, E. L.;
Carbery, D. R. Org. Biomol. Chem. 2012, 10, 1406.
(2) Hirano, S.; Fukudome, Y.; Tanaka, R.; Sato, F.; Urabe, H.
Tetrahedron 2006, 62, 3896.
(3) (a) Barbazanges, M.; Meyer, C.; Cossy, J. Org. Lett. 2007, 9, 3245.
(b) Barbazanges, M.; Meyer, C.; Cossy, J. Tetrahedron Lett. 2008, 49,
2902. (c) Barbazanges, M.; Meyer, C.; Cossy, J.; Turner, P. Chem.
Eur. J. 2011, 17, 4480.
(4) Valenta, P.; Carroll, P. J.; Walsh, P. J. J. Am. Chem. Soc. 2010, 132,
14179.
(5) (a) Tanaka, R.; Hirano, S.; Urabe, H.; Sato, F. Org. Lett. 2003, 5,
67. (b) Hirano, S.; Tanaka, R.; Urabe, H.; Sato, F. Org. Lett. 2004, 6,
727. (c) Saito, N.; Katayama, T.; Sato, Y. Org. Lett. 2008, 10, 3829.
́ ́
(6) Castro, J.; Coteron, J. M.; Fraile, M. T.; García-Ochoa, S.; Gomez
de las Heras, F.; Martín-Cuesta, A. Tetrahedron Lett. 2002, 43, 1851.
(7) For selected reviews, see: (a) Ramirez, T. A.; Zhao, B.; Shi, Y.
Chem. Soc. Rev. 2012, 41, 931. (b) Obora, Y.; Ishii, Y. Catalysts 2013, 3,
794. (c) Louillat, M.-L.; Patureau, F. W. Chem. Soc. Rev. 2014, 43, 901.
(8) For selected examples on sp2 C−H amination, see: (a) Tan, Y.;
Hartwig, J. F. J. Am. Chem. Soc. 2010, 132, 3676. (b) Yoo, E. J.; Ma, S.;
Mei, T.-S.; Chan, K. S. L.; Yu, J.-Q. J. Am. Chem. Soc. 2011, 133, 7652.
(c) Xiao, B.; Gong, T.-J.; Xu, J.; Liu, Z.-J.; Liu, L. J. Am. Chem. Soc.
2011, 133, 1466. (d) Kantak, A. A.; Potavathri, S.; Barham, R. A.;
Romano, K. M.; DeBoef, B. J. Am. Chem. Soc. 2011, 133, 19960.
(e) Antonchick, A. P.; Samanta, R.; Kulikov, K.; Lategahn, J. Angew.
Chem., Int. Ed. 2011, 50, 8605. (f) Kim, H.; Shin, K.; Chang, S. J. Am.
Chem. Soc. 2014, 136, 5904.
(9) For selected examples on sp3 C−H amination, see: (a) Reed, S.
A.; Mazzotti, A. R.; White, M. C. J. Am. Chem. Soc. 2009, 131, 11701.
(b) Neumann, J.; Rakshit, S.; Droge, T.; Glorius, F. Angew. Chem., Int.
̈
Ed. 2009, 48, 6892. (c) Shimizu, Y.; Obora, Y.; Ishii, Y. Org. Lett. 2010,
12, 1372. (d) Pan, J.; Su, M.; Buchwald, S. L. Angew. Chem., Int. Ed.
2011, 50, 8647. (e) Souto, J. A.; Zian, D.; Muniz, K. J. Am. Chem. Soc.
̃
2012, 134, 7242. (f) Kang, T.; Kim, Y.; Lee, D.; Wang, Z.; Chang, S. J.
Am. Chem. Soc. 2014, 136, 4141.
́
́
́
(10) (a) Iglesias, A.; Alvarez, R.; R. de Lera, A.; Muniz, K. Angew.
̃
Chem., Int. Ed. 2012, 51, 2225. (b) Ni, Z.; Zhang, Q.; Xiong, T.;
Zheng, Y.; Li, Y.; Zhang, H.; Zhang, J.; Liu, Q. Angew. Chem., Int. Ed.
2012, 51, 1244. (c) Xiong, T.; Li, Y.; Mao, L.; Zhang, Q.; Zhang, Q.
Chem. Commun. 2012, 48, 2246. (d) Boursalian, G. B.; Ngai, M.-Y.;
Hojczyk, K. N.; Ritter, T. J. Am. Chem. Soc. 2013, 135, 13278.
(e) Wang, S.; Ni, Z.; Huang, X.; Wang, J.; Pan, Y. Org. Lett. 2014, 16,
5648.
(11) (a) Hegedus, L. S.; McKearin, J. M. J. Am. Chem. Soc. 1982, 104,
2444. (b) Krolski, M. E.; Renaldo, A. F.; Rudisill, D. E.; Stille, J. K. J.
Org. Chem. 1988, 53, 1170. (c) Liwosz, T. W.; Chemler, S. R. Chem.
Eur. J. 2013, 19, 12771. (d) Kim, J.; Chang, S. Angew. Chem., Int. Ed.
2014, 53, 2203.
(12) (a) Trenner, J.; Depken, C.; Weber, T.; Breder, A. Angew.
Chem., Int. Ed. 2013, 52, 8952. (b) Breder, A. Synlett 2014, 25, 899.
(13) For reviews, see: (a) Organoselenium Chemistry: Synthesis and
Reactions; Wirth, T., Ed.; Wiley-VCH: Weinheim, 2011. (b) Sarma, B.
K.; Mugesh, G. Org. Biomol. Chem. 2008, 6, 965. (c) Freudendahl, D.
M.; Shahzad, S. A.; Wirth, T. Eur. J. Org. Chem. 2009, 1649.
(d) Freudendahl, D. M.; Santoro, S.; Shahzad, S. A.; Santi, C.; Wirth,
T. Angew. Chem., Int. Ed. 2009, 48, 8409.
(14) For selected examples, see: (a) Tunge, J. A.; Mellegaard, S. R.
Org. Lett. 2004, 6, 1205. (b) Crich, D.; Zou, Y. J. Org. Chem. 2005, 70,
3309. (c) Santoro, S.; Santi, C.; Sabatini, M.; Testaferri, L.; Tiecco, M.
1837
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