Frustrated Lewis Pair Mediated 1, 2‐Hydrocarbation of Alkynes. (4th July 2017)

• Record Type: Journal Article
• Authors: Fasano, Valerio; Curless, Liam D.; Radcliffe, James E.; Ingleson, Michael J.
• Is Part Of: Angewandte Chemie. Volume 129:Number 31(2017)
• Page Start: 9330
• Page End: 9334
• Publication Date: 2017-07-04
• Subjects: 1, 2-Hydrocarbierung -- Alkine -- Carbokationen -- Frustrierte Lewis-Paare -- Hydridtransfer; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201705100
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: Frustrated Lewis pair (FLP) chemistry enables a rare example of alkyne 1, 2‐hydrocarbation with N‐methylacridinium salts as the carbon Lewis acid. This 1, 2‐hydrocarbation process does not proceed through a concerted mechanism as in alkyne syn‐hydroboration, or through an intramolecular 1, 3‐hydride migration as operates in the only other reported alkyne 1, 2‐hydrocarbation reaction. Instead, in this study, alkyne 1, 2‐hydrocarbation proceeds by a novel mechanism involving alkyne dehydrocarbation with a carbon Lewis acid based FLP to form the new C−C bond. Subsequently, intermolecular hydride transfer occurs, with the Lewis acid component of the FLP acting as a hydride shuttle that enables alkyne 1, 2‐hydrocarbation.