Methylsulfenylation of Electrophilic Carbon Atoms: Reaction Development, Scope, and Mechanism. Issue 12 (27th January 2017)

• Record Type: Journal Article
• Authors: Pereira, Adriane A.; Pereira, Amanda S.; de Mello, Amanda C.; Carpanez, Arthur G.; Horta, Bruno A. C.; Amarante, Giovanni W.
• Is Part Of: European journal of organic chemistry. Issue 12(2017)
• Page Start: 1578
• Page End: 1582
• Publication Date: 2017-01-27
• Subjects: Activated carbons -- Chemoselectivity -- Microwave reactions -- Organocatalysis -- Sulfur -- Density functional calculations; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201601613
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : An innovative method for the methylsulfenylation of electrophilic carbons was explored. Cheap and commercially available dimethyl sulfoxide (DMSO) was used as a source of the –SCH3 group. Chalcone, dibenzylideneacetone, and Morita–Baylis–Hillman adduct derivatives were successfully sulfenylated to give the corresponding products in moderate to high yields. Control experiments and DFT calculations revealed deoxygenation of DMSO and nucleophilic addition of a sulfur intermediate as key steps in the entire mechanism. Abstract : The methylsulfenylation of activated carbons is now possible by using DMSO. A combined metal‐free process and microwave irradiation allow chemoselective C–S bond formation.