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Journal Of Organic Chemistry

Publication date: 2020-02-21
Volume: 85 Pages: 2250 - 2259
Publisher: American Chemical Society

Author:

Storozhenko, Olga A
Festa, Alexey A ; Detistova, Galina I ; Rybakov, Victor B ; Varlamov, Alexey V ; Van der Eycken, Erik V ; Voskressensky, Leonid G

Keywords:

Science & Technology, Physical Sciences, Chemistry, Organic, Chemistry, CYSTEINE PROTEASE INHIBITOR, VINYL SULFONES, DECARBOXYLATIVE SULFONYLATION, STEREOSELECTIVE-SYNTHESIS, CINNAMIC-ACIDS, SULFUR-DIOXIDE, EOSIN Y, C-S, LIGHT, ARYL, 0304 Medicinal and Biomolecular Chemistry, 0305 Organic Chemistry, Organic Chemistry, 3404 Medicinal and biomolecular chemistry, 3405 Organic chemistry

Abstract:

(Het)Arylallenes undergo hydrosulfonylation under photoredox-catalyzed conditions. The reaction gives vinyl sulfones in a regio- and diastereoselective manner, employing sodium sulfinates as the sulfonyl source and eosin Y as the photocatalyst. Indol-1-yl, pyrrol-1-yl, phenyl, and naphtylallenes might be used. Aliphatic allenes are incompatible with the reaction conditions.