Brønsted acid-catalysed desilylative heterocyclisation to form substituted furans. Issue 1 (6th December 2022)

• Record Type: Journal Article
• Authors: Babcock, Emily G.; Rahman, Md. Shafiqur; Taylor, James E.
• Is Part Of: Organic & biomolecular chemistry. Volume 21:Issue 1(2022)
• Page Start: 163
• Page End: 168
• Publication Date: 2022-12-06
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d2ob01828d
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A new catalytic dehydrative heterocyclisation to form mono-, di-, and tri-substituted furans under mild conditions. Abstract : Heterocyclisation of tert -butyldimethylsilyl (TBS) protected γ-hydroxy-α, β-unsaturated ketones catalysed by para -toluenesulfonic acid ( p -TSA) to form substituted furans is reported. The reaction proceeds under mild conditions at room temperature in methanol to give a range of furan products (21 examples, up to 98% yield). Mechanistic experiments suggest the reaction proceeds via in situ deprotection followed by catalytic dehydrative heterocyclisation.