Metal-Free Electrophilic Alkynylation of Sulfenate Anions with Ethynylbenziodoxolone Reagents

Metal-Free Electrophilic Alkynylation of Sulfenate Anions with Ethynylbenziodoxolone Reagents

Alkynyl sulfoxides are important building blocks with a unique reactivity in organic chemistry, but only a few reliable methods have been reported to synthesize them. A novel route to access alkynyl sulfoxides is reported herein by using ethynyl benziodoxolone (EBX) reagents to trap sulfenate anions...

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Bibliographic Details
Published in:Journal of organic chemistry Vol. 84; no. 6; pp. 3687 - 3701
Main Authors: Amos, Stephanie G. E, Nicolai, Stefano, Gagnebin, Alec, Le Vaillant, Franck, Waser, Jerome
Format: Journal Article
Language:English
Published: United States American Chemical Society 15-03-2019
Online Access:Get full text
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Summary:Alkynyl sulfoxides are important building blocks with a unique reactivity in organic chemistry, but only a few reliable methods have been reported to synthesize them. A novel route to access alkynyl sulfoxides is reported herein by using ethynyl benziodoxolone (EBX) reagents to trap sulfenate anions generated in situ, via a retro-Michael reaction. The reaction takes place under metal-free and mild conditions. It is compatible with aryl, heteroaryl, and alkyl sulfoxides with up to 90% yield. This practical access to alkynyl sulfoxides is expected to facilitate the application of these useful building blocks in organic synthesis.
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.9b00050