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

doi:10.1021/jacs.8b11039

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

J Am Chem Soc. 2019 Jan 30;141(4):1593-1598. doi: 10.1021/jacs.8b11039. Epub 2019 Jan 22.

Authors

Binbin Liu¹, Yongquan Ning¹, Matteo Virelli², Giuseppe Zanoni², Edward A Anderson³, Xihe Bi^{1

4}

Affiliations

¹ Department of Chemistry , Northeast Normal University , Changchun 130024 , China.
² Department of Chemistry , University of Pavia , Viale Taramelli 12 , 27100 , Pavia , Italy.
³ Chemistry Research Laboratory , University of Oxford , 12 Mansfield Road , Oxford OX1 3TA , United Kingdom.
⁴ State Key Laboratory of Elemento-Organic Chemistry , Nankai University , Tianjin 300071 , China.

PMID: 30667220
DOI: 10.1021/jacs.8b11039

Abstract

An unprecedented conversion of terminal alkynes into N-sulfonimidamides (amidines) is reported by a silver-catalyzed, one-pot, four-component reaction with TMSN₃, sodium sulfinate, and sulfonyl azide. The reaction scope includes both aromatic and aliphatic alkynes. A possible cascade reaction mechanism, consisting of alkyne hydroazidation, sulfonyl radical addition, 1,3-dipolar cycloaddition by TMSN₃, and retro-1,3-dipolar cycloaddition, is proposed. TMSN₃ is found to play an essential role in each step of the reaction.

Publication types

Research Support, Non-U.S. Gov't