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Direct Transformation of Secondary Amides into Secondary Amines: Triflic Anhydride Activated Reductive Alkylation

Authors

  • Kai-Jiong Xiao,

    1. Department of Chemistry and Fujian Provincial Key Laboratory for Chemical Biology, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005 (P.R. China)
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  • Dr. Ai-E Wang,

    1. Department of Chemistry and Fujian Provincial Key Laboratory for Chemical Biology, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005 (P.R. China)
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  • Prof. Dr. Pei-Qiang Huang

    Corresponding author
    1. Department of Chemistry and Fujian Provincial Key Laboratory for Chemical Biology, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005 (P.R. China)
    • Department of Chemistry and Fujian Provincial Key Laboratory for Chemical Biology, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005 (P.R. China)
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  • The authors are grateful to the National Basic Research Program (973 Program) of China (Grant No. 2010CB833200), the NSF of China (21072160; 20832005), and the Fundamental Research Funds for the Central Universities of China (Grant No. 201112G001)for financial support, and for a Scholarship Award for Excellent Doctoral Student granted by Ministry of Education of China (2010). We are grateful to Prof. Dr. G. M. Blackburn for valuable discussions and to Y.-H. for the preparation of some starting materials.

Abstract

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Versatile and mild: The first general method for the title transformation has been developed (see scheme; 2-F-Py=2-fluoropyridine; Tf=trifluorosulfonyl). The amines are synthesized in good yields and the ketimine intermediates can be isolated before the reduction. This method should find applications in the synthesis of nitrogen-containing bioactive molecules and medicinal agents.

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