A one-pot metal-free protocol for the synthesis of chalcogenated furans from 1, 4-enediones and thiols. Issue 4 (11th January 2019)

• Record Type: Journal Article
• Authors: Rajeshkumar, Venkatachalam; Neelamegam, Chinnaraj; Anandan, Sambandam
• Is Part Of: Organic & biomolecular chemistry. Volume 17:Issue 4(2018)
• Page Start: 982
• Page End: 991
• Publication Date: 2019-01-11
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c8ob03051k
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : Transition-metal-free synthesis of chalcogenated furans through the sequential thiol-Michael/Paal–Knorr reaction of 1, 4-enediones in the presence of a catalytic amount of p -toluene sulfonic acid has been developed. Abstract : Transition-metal-free synthesis of chalcogenated furans through the sequential thiol-Michael/Paal–Knorr reaction of 1, 4-enediones in the presence of a catalytic amount of p -toluenesulfonic acid has been developed. The present one-pot strategy involves the thiol Michael addition to 1, 4-enediones in an anti-Markovnikov fashion with the formation of a new C–S bond, followed by intramolecular dehydrative annulation in the presence of cat . TsOH delivering fully substituted furans in good to excellent yields (50–99%). The reaction is compatible with a wide range of substrates and also capable of multi-gram scale synthesis of chalcogenated furans.