Chinese Journal of Organic Chemistry >
Oxidative Cross Coupling of sp3-C—H Bonds Catalyzed by Bu4NAuCl4 with H2O2 as Oxidant
Received date: 2012-10-17
Revised date: 2012-10-29
Online published: 2012-10-31
Supported by
Project supported by the National Natural Science Foundation of China (No. 21074054) and the Innovation Experiment Program for University Students of Jiangsu Province.
Activation of two sp3-C—H bonds and oxidative alkylation of sp3-C—H bond adjacent to a nitrogen atom of tertiary amine were catalyzed by Bu4NAuCl4 with H2O2 as oxidant under mild reaction conditions. The safe, convenient, and environmentally benign process, as well as the broad substrate scope, low catalyst loading, high selectivity, short reaction time, and good yields make the protocol very practical.
Zhang Yan , Zhu Chengjian . Oxidative Cross Coupling of sp3-C—H Bonds Catalyzed by Bu4NAuCl4 with H2O2 as Oxidant[J]. Chinese Journal of Organic Chemistry, 2012 , 32(11) : 2090 -2094 . DOI: 10.6023/cjoc201210029
[1] For representative reviews, see:
(a) Crabtree, R. H. J. Organomet. Chem. 2004, 689, 4083.
(b) Ritleng, V.; Sirlin, C.; Pfeffer, M. Chem. Rev. 2002, 102, 1731.
(c) Jia, C.; Kitamura, T.; Fujiwara, Y. Acc. Chem. Res. 2001, 34, 633.
(d) Dyker, G. Angew. Chem., Int. Ed. 1999, 38, 1698.
(e) Shilov, A. E.; Shul'pin, G. B. Chem. Rev. 1997, 97, 2879.
(f) Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Acc. Chem. Res. 1995, 28, 154.
[2] Diederich, F., Stang, P. J. Metal-Catalyzed Cross-Coupling Reactions, Wiley-VCH, New York, 1998.
[3] (a) Li, Z.; Li, C.-J. Org. Lett. 2004, 6, 4997.
(b) Li, Z.; Li, C.-J. J. Am. Chem. Soc. 2004, 126, 11810.
(c) Murahashi, S.-I.; Komiya, N.; Terai, H.; Nakae, T. J. Am. Chem. Soc. 2003, 125, 15312.
(d) Murata, S.; Teramoto, K.; Miura, M.; Nomura, M. J. Chem. Res., Miniprint 1993, 2827.
[4] (a) Hatamoto, Y.; Sakaguchi, S.; Ishii, Y. Org. Lett. 2004, 6, 4623.
(b) Yokota, T.; Tani, M.; Sakaguchi, S.; Ishii, Y. J. Am. Chem. Soc. 2003, 125, 1476.
(c) Tsuji, J.; Nagashima, H. Tetrahedron 1984, 40, 2699.
[5] (a) DeBoef, B.; Pastine, S. J.; Sames, D. J. Am. Chem. Soc. 2004, 126, 6556.
(b) Lin, Y.; Ma, D.; Lu, X. Tetrahedron Lett. 1987, 28, 3249.
[6] (a) Nicolaou, K. C.; Petasis, N. A.; Zipkin, R. E. J. Am. Chem. Soc. 1982, 104, 5560.
(b) Nicolaou, K. C.; Zipkin, R. E.; Petasis, N. A. J. Am. Chem. Soc. 1982, 104, 5558.
(c) Nicolaou, K. C.; Petasis, N. A.; Uenishi, J.; Zipkin, R. E. J. Am. Chem. Soc. 1982, 104, 5557.
(d) Nicolaou, K. C.; Petasis, N. A.; Zipkin, R. E.; Uenishi, J. J. Am. Chem. Soc. 1982, 104, 5555.
[7] Lucet, D.; Le Gall, T.; Mioskowski, C. Angew. Chem., Int. Ed. 1998, 37, 2580.
[8] Baer, H. H.; Urbas, L. In The Chemistry of the Nitro and Nitroso Group, Ed.: Patai, S., Interscience, New York, 1970, Part 2, p. 117.
[9] (a) Yan, G. B.; Yu, J.; Zhang, L. Chin. J. Org. Chem. 2012, 32, 294 (in Chinese).
(严国兵, 于健, 张玲, 有机化学, 2012, 32, 294.)
(b) Xie, J. H.; Zhou, Q. L. Acta Chim. Sinica 2012, 70, 1427 (in Chinese).
(谢建华, 周其林, 化学学报, 2012, 70, 1427.)
(c) Li, Y. Q.; Cao, Y. C.; Ye, X. F.; Zhou, H. Chin. J. Org. Chem. 2011, 31, 1538 (in Chinese).
(李永清, 曹育才, 叶晓峰, 周慧, 有机化学, 2011, 31, 1538.)
(d) Wang, C. X.; Li, X. C.; Xu, F.; Wan, B. S. Prog. Chem. 2010, 22, 610 (in Chinese).
王春翔, 李新成, 徐粉, 万伯顺, 化学进展, 2010, 22, 610.)
(e) Gu, S. J.; Ni, P.; Chen, W. Z. Chin. J. Catal. 2010, 31, 875 (in Chinese).
(顾绍金, 倪鹏, 陈万芝, 催化学报, 2010, 31, 875.)
(f) Pan, F.; Shi, Z. J. Acta Chim. Sinica 2012, 70, 1679 (in Chinese).
(潘菲, 施章杰, 化学学报, 2012, 70, 1679.)
(g) Qin, Y. C.; Peng, Q. Chin. J. Org. Chem. 2011, 31, 1169 (in Chinese).
(秦元成, 彭强, 有机化学, 2011, 31, 1169.)
(h) Wang, N. X. Chin. J. Org. Chem. 2011, 31, 1319 (in Chinese).
(王乃兴, 有机化学, 2011, 31, 1319.)
(i) Weng, J. Q.; Yu, Z. Q.; Zhang, G. F. Prog. Chem. 2012, 24, 523 (in Chinese).
(翁建全, 余志勤, 张国富, 化学进展, 2012, 24, 523.)
(j) Yuan, Y. Q.; Guo, S. R.; Mo, J. J.; Qian, L.; Shi, Z. F. Chin. J. Org. Chem. 2012, 32, 732 (in Chinese).
(袁艳琴, 郭圣荣, 莫建军, 钱利, 石泽凤, 有机化学, 2012, 32, 732.)
(k) Yu, H. Z.; Fu, R.; Bai, X. Y.; Guo, Q. X. Prog. Chem. 2010, 22, 557 (in Chinese).
(于海珠, 傅尧, 白小宇, 郭庆祥, 化学进展, 2010, 22, 557.)
(l) Li, J. S.; Cai, F. F.; Li, Z. W.; Xue, Y.; Cheng, C.; Liu, W. D.; Cao, Z. Chin. J. Chem. 2012, 30, 1699.
[10] Li, Z. P.; Li, C. J. J. Am. Chem. Soc. 2005, 127, 3672.
[11] (a) Balse, O.; Borduas, N.; Dubois, P.; Chapuzet, J. M.; Chan, T. H.; Lessard, J.; Li, C. J. Chem. Eur. J. 2010, 16, 8162.
(b) Neumann, M.; Zeitler, K. Org. Lett. 2012, 14, 2658.
(c) Condie, A. G.; Gonalez-Gomez, J. C.; Stephenson, C. R. J. J. Am. Chem. Soc. 2010, 132, 1464.
(d) Shu, X. Z.; Xia, X. F.; Yang, Y. F.; Ji, K. G.; Liu, X. Y.; Liang, Y. M. J. Org. Chem. 2009, 74, 7464.
[12] (a) Hashmi, A.; Stephen, K.; Schuster, A. M.; Litters, S.; Rominger, F.; Pernpointner, M. Chem.-Eur. J. 2011, 17, 5661.
(b) Zhang, Y.; Peng, H.; Zhang, M.; Cheng, Y. X.; Zhu, C. J. Chem. Commun. 2011, 2354.
(c) Xie, J.; Li, H. M.; Zhou, J. C.; Cheng, Y. X.; Zhu, C. J. Angew. Chem. 2012, 124, 1278.
[13] (a) Boess, E.; Schmitz, C.; Klussmann, M. J. Am. Chem. Soc. 2012, 134, 5317.
(b) Zhou. H. W.; Huang, X.; Chen, W. L. J. Org. Chem. 2004, 69, 5471.
(c) Huang, J. W.; Shi, M. J. Org. Chem. 2005, 70, 3859.
(d) Yu, L.; Huang, X. Synlett 2007, 1371.
(e) Chen, W. L.; Huang, X.; Zhou, H. W. Synthesis 2006, 609.
[14] Condie, A. G.; Gonzalez-Gomez, J. C.; Stephenson, C. R. J. J. Am. Chem. Soc. 2010, 132, 1464.
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