Cs₂CO₃-Mediated Regio- and Stereoselective Sulfonylation of 1,1-Dibromo-1-alkenes with Sodium Sulfinates

This paper is dedicated to Professor Majid M. Heravi on the occasion of his 68^th birthday.

Abstract

A highly selective synthesis of (Z)-1-bromo-1-sulfonyl alkenes via Cs₂CO₃-promoted sulfonylation of 1,1-dibromo-1-alkenes with sodium sulfinates is described. Notably, using excess amounts of Cs₂CO₃ and sodium sulfinate in such a reaction regenerated the parent aldehyde. Interestingly, the reaction of 1-(2,2-dibromovinyl)-2-nitrobenzene in the presence of sulfinates and Cs₂CO₃ produced isatin. The Sonogashira cross coupling of synthesized (Z)-1-bromo-1-sulfonyl alkenes with phenylacetylene gave selectively the corresponding sulfonylalkynyl alkenes.

Key words

1,1-dibromo-1-alkenes - sodium sulfonates - regioselective - vinyl sulfone - cesium carbonate - isatin

Publikationsverlauf

Eingereicht: 10. Juli 2020

Angenommen nach Revision: 22. August 2020

Artikel online veröffentlicht:
06. Oktober 2020

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