Chinese Journal of Catalysis ›› 2015, Vol. 36 ›› Issue (8): 1175-1182.DOI: 10.1016/S1872-2067(15)60872-5

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Rh(III)-catalyzed direct C-H cyanation of N-methoxybenzamides using N-cyano-N-phenyl-p-toluenesulfonamide

Siwei Zhanga,b, Jie Zhoub, Jingjing Shib, Min Wanga, H. Eric Xub,c, Wei Yib   

  1. a School of Life Science and Biotechnology, China Pharmaceutical University, Nanjing 210009, Jiangsu, China;
    b VARI/SIMM Center, Center for Structure and Function of Drug Targets, CAS-Key Laboratory of Receptor Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China;
    c Laboratory of Structural Sciences, Program on Structural Biology and Drug Discovery, Van Andel Research Institute, Grand Rapids, Michigan 49503, USA
  • Received:2015-04-14 Revised:2015-04-21 Online:2015-07-29 Published:2015-07-30
  • Supported by:

    This work was supported by Shanghai Municipal Natural Science Foundation, China (15ZR1447800) and the Chinese Postdoctoral Science Foundation (2012M511158, 2013T60477, 2014M560363).

Abstract:

A new method has been developed for the mild and efficient Rh(III)-catalyzed direct C-H cyanation of a diverse range of N-methoxybenzamides using N-cyano-N-phenyl-p-toluenesulfonamide as an environmentally friendly and efficient cyanating reagent. This new reaction proceeded with good regioselectivity to provide direct access to a wide variety of valuable ortho-cyanated N- methoxybenzamides with board substrate/functional group tolerance.

Key words: Rhoduim(III) catalyst, C-H cyanation, N-methoxybenzamides, N-cyano-N-phenyl-p-toluenesulfonamide, Reaction mechanism