Organic Letters
Letter
(2) Pioneering examples of amination of aryl chlorides: (a) Wolfe, J.
P.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 6054. (b) Old, D. W.;
Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 9722.
(3) The first example of amination of aryl tosylates: Hamann, B. C.;
Hartwig, J. F. J. Am. Chem. Soc. 1998, 120, 7369.
(4) Pioneering examples of amination of aryl mesylates: (a) So, C.
M.; Zhou, Z.; Lau, C.; Kwong, F. Y. Angew. Chem., Int. Ed. 2008, 47,
6402. (b) Fors, B. P.; Watson, D. A.; Biscoe, M. R.; Buchwald, S. L. J.
Am. Chem. Soc. 2008, 130, 13552.
(5) Amination of aryl phosphates: Huang, J.-H.; Yang, L.-M. Org.
Lett. 2011, 13, 3750.
(6) Amination of aryl sulfamates: (a) Ramgren, S. D.; Silberstein, A.
L.; Yang, Y.; Garg, N. K. Angew. Chem., Int. Ed. 2011, 50, 2171.
(b) Hie, L.; Ramgren, S. D.; Mesganaw, T.; Garg, N. K. Org. Lett.
2012, 14, 4182.
(7) Amination of aryl carbamates: Mesganaw, T.; Silberstein, A. L.;
Ramgren, S. D.; Nathel, N. F. F.; Hong, X.; Liu, P.; Garg, N. K. Chem.
Sci. 2011, 2, 1766.
(8) Amination of aryl esters: (a) Shimasaki, T.; Tobisu, M.; Chatani,
N. Angew. Chem., Int. Ed. 2010, 49, 2929. (b) Yue, H.; Guo, L.; Liu, X.;
Rueping, M. Org. Lett. 2017, 19, 1788.
(9) Amination of aryl ethers: (a) Tobisu, M.; Shimasaki, T.; Chatani,
N. Chem. Lett. 2009, 38, 710. (b) Tobisu, M.; Yasutome, A.;
Yamakawa, K.; Shimasaki, T.; Chatani, N. Tetrahedron 2012, 68, 5157.
(c) Li, J.; Wang, Z.-X. Org. Lett. 2017, 19, 3723.
(10) Decarbonylative amination of esters: Yue, H.; Guo, L.; Liao, H.-
H.; Cai, Y.; Zhu, C.; Rueping, M. Angew. Chem., Int. Ed. 2017, 56,
4282.
(11) Decarbonylative amination of amides: (a) Liu, X.; Yue, H.; Jia,
J.; Guo, L.; Rueping, M. Chem. - Eur. J. 2017, 23, 11771. (b) Lee, S.-C.;
Guo, L.; Yue, H.; Liao, H.-H.; Rueping, M. Synlett 2017, 28, 2594.
(12) Account: Gao, K.; Otsuka, S.; Baralle, A.; Nogi, K.; Yorimitsu,
H.; Osuka, A. J. Synth. Org. Chem., Jpn. 2016, 74, 1119.
(13) Recent examples: (a) Gao, K.; Yorimitsu, H.; Osuka, A. Angew.
Chem., Int. Ed. 2016, 55, 4573. (b) Baralle, A.; Yorimitsu, H.; Osuka, A.
Chem. - Eur. J. 2016, 22, 10768. (c) Saito, H.; Nogi, K.; Yorimitsu, H.
Chem. Lett. 2017, 46, 1122. (d) Gao, K.; Yamamoto, K.; Nogi, K.;
Yorimitsu, H. Synlett 2017, 28, 2956.
(14) Reviews: (a) Sugimura, H.; Okamura, H.; Miura, M.; Yoshida,
M.; Takei, H. Nippon Kagaku Kaishi 1985, 416. (b) Naso, F. Pure Appl.
Chem. 1988, 60, 79. (c) Luh, T.-Y.; Ni, Z.-J. Synthesis 1990, 1990, 89.
(d) Luh, T.-Y. Acc. Chem. Res. 1991, 24, 257. (e) Fiandanese, V. Pure
Appl. Chem. 1990, 62, 1987. (f) Dubbaka, S. R.; Vogel, P. Angew.
́
Chem., Int. Ed. 2005, 44, 7674. (g) Prokopcova, H.; Kappe, C. O.
Angew. Chem., Int. Ed. 2008, 47, 3674. (h) Wang, L.; He, W.; Yu, Z.
Chem. Soc. Rev. 2013, 42, 599. (i) Modha, S. G.; Mehta, V. P.; Van der
Eycken, E. V. Chem. Soc. Rev. 2013, 42, 5042. (j) Pan, F.; Shi, Z.-J. ACS
Catal. 2014, 4, 280.
(15) (a) Sugahara, T.; Murakami, K.; Yorimitsu, H.; Osuka, A. Angew.
Chem., Int. Ed. 2014, 53, 9329. (b) Gao, K.; Yorimitsu, H.; Osuka, A.
Eur. J. Org. Chem. 2015, 2015, 2678.
(16) (a) Yamamoto, K.; Otsuka, S.; Nogi, K.; Yorimitsu, H. ACS
Catal. 2017, 7, 7623. (b) Saito, H.; Nogi, K.; Yorimitsu, H. Synthesis
2017, 49, 4769. (c) Yoshida, Y.; Nogi, K.; Yorimitsu, H. Synlett 2017,
28, 2561.
(17) (a) Kantchev, E. A. B.; Ying, J. Y. Organometallics 2009, 28, 289.
(b) Peh, G.-R.; Kantchev, E. A. B.; Er, J.-C.; Ying, J. Y. Chem. - Eur. J.
2010, 16, 4010.
(18) Reviews: (a) Kantchev, E. A. B.; O’Brien, C. J.; Organ, M. G.
Aldrichimica Acta 2006, 39, 117. (b) Organ, M. G.; Chass, G. A.; Fang,
D.-C.; Hopkinson, A. C.; Valente, C. Synthesis 2008, 2008, 2776.
(c) Valente, C.; Çalimsiz, S.; Hoi, K. H.; Mallik, D.; Sayah, M.; Organ,
M. G. Angew. Chem., Int. Ed. 2012, 51, 3314.
(19) Alkanesulfenate anions are regarded as being less stable than
arenesulfenate anions: (a) Soderman, S. C.; Schwan, A. L. Org. Lett.
2011, 13, 4192. (b) Jia, T.; Zhang, M.; Jiang, H.; Wang, C. Y.; Walsh,
P. J. J. Am. Chem. Soc. 2015, 137, 13887.
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