Direct Transformation of Terminal Alkynes into Amidines by a Silver-Catalyzed Four-Component Reaction

Binbin Liu, Yongquan Ning, Matteo Virelli, Giuseppe Zanoni, Edward A. Anderson, Xihe Bi*

*Department of Chemistry, Northeast Normal University, Changchun 130024, China, Email: bixh507nenu.edu.cn

B. Liu, Y. Ning, M. Virelli, G. Zanoni, E. A. Anderson, X. Bi, J. Am. Chem. Soc., 2019, 141, 1593-1598.

DOI: 10.1021/jacs.8b11039

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Abstract

A silver-catalyzed, one-pot, four-component reaction of terminal alkynes, TMSN₃, sodium sulfinate, and sulfonyl azide provides amidines. A possible cascade reaction mechanism consists of alkyne hydroazidation, sulfonyl radical addition, 1,3-dipolar cycloaddition of TMSN₃, and retro-1,3-dipolar cycloaddition.

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proposed mechanism

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Key Words

amidines (C=N, C-N), multicomponent reactions

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ID: J48-Y2019