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

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

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 mechan...

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Veröffentlicht in:Journal of the American Chemical Society 2019-01, Vol.141 (4), p.1593-1598
Hauptverfasser: Liu, Binbin, Ning, Yongquan, Virelli, Matteo, Zanoni, Giuseppe, Anderson, Edward A, Bi, Xihe
Format: Artikel
Sprache:eng
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Zusammenfassung: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.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.8b11039