Journal of Organic Chemistry p. 3687 - 3701 (2019)
Update date:2022-08-03
Topics: Product Formation Reaction Mechanism Metal-free Sulfenate Anion (R-SO2-) Ethynylbenziodoxolone Reagents
Amos, Stephanie G. E.
Nicolai, Stefano
Gagnebin, Alec
Le Vaillant, Franck
Waser, Jerome
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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Doi:10.1016/S0008-6215(00)00211-1
(2000)Doi:10.1021/ja00143a011
(1995)Doi:10.1016/S0008-6215(00)00238-X
(2000)Doi:10.1016/S0957-4166(00)00323-2
(2000)Doi:10.1039/jr9650004566
(1965)Doi:10.1021/jo00107a003
(1995)