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2012 , Vol. 32 >Issue 11: 2090 - 2094

DOI: https://doi.org/10.6023/cjoc201210029

研究论文

Bu4NAuCl4催化的H2O2氧化的sp3-C—H键与sp3-C—H键的交叉偶联反应

  • 张艳 ,
  • 朱成建
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  • a 江南大学医药学院 无锡 214122;
    b 南京大学化学化工学院 南京 210093

收稿日期: 2012-10-17

  修回日期: 2012-10-29

  网络出版日期: 2012-10-31

基金资助

国家自然科学基金(No. 21074054)和2012江苏省大学生创新训练资助项目.

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Oxidative Cross Coupling of sp3-C—H Bonds Catalyzed by Bu4NAuCl4 with H2O2 as Oxidant

  • Zhang Yan ,
  • Zhu Chengjian
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  • a School of Medicine and Pharmaceutics, Jiangnan University, Wuxi 214122;
    b State Key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093

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.

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摘要

以Bu4NAuCl4为催化剂, H2O2作为氧化剂, 在温和的反应条件下实现了叔胺氮的邻位碳原子上sp3-C—H与硝基烷烃的氧化偶联. 反应条件温和, 室温、空气下即可进行, 适用范围广泛, 产率高, 后处理方便. 为新的C—C键的形成提供了一条简洁高效的反应路径, 并且合成了一系列可能具有重要药理和生物活性的β-硝基氨化合物.

关键词： sp3-C—H活化; 交叉脱氢偶联; 氧化烷基化; 金催化剂

本文引用格式

张艳 , 朱成建 . Bu4NAuCl4催化的H2O2氧化的sp3-C—H键与sp3-C—H键的交叉偶联反应[J]. 有机化学, 2012 , 32(11) : 2090 -2094 . DOI: 10.6023/cjoc201210029

Abstract

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.

Key words： sp3-C—H activation; cross-dehydrogenative coupling; oxidative alkylation; gold catalyst

参考文献

[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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