32018-21-6Relevant academic research and scientific papers
Metal-Free Electrophilic Alkynylation of Sulfenate Anions with Ethynylbenziodoxolone Reagents
Amos, Stephanie G. E.,Nicolai, Stefano,Gagnebin, Alec,Le Vaillant, Franck,Waser, Jerome
, p. 3687 - 3701 (2019)
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.
Organocatalytic asymmetric synthesis of sulfoxides from sulfenic acid anions mediated by a cinchona -derived phase-transfer reagent
Gelat, Fabien,Jayashankaran, Jayadevan,Lohier, Jean-Francois,Gaumont, Annie-Claude,Perrio, Stephane
supporting information; experimental part, p. 3170 - 3173 (2011/08/06)
Preliminary results concerning a conceptually novel route to chiral sulfoxides based on the asymmetric alkylation of sulfenate salts with alkyl halides mediated by a chiral phase-transfer catalyst are described. As a representative example, o-anisyl methyl sulfoxide was produced in 96% yield and with an enantiomeric excess of 58% using commercial cinchonidinium derivative 2a.
