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Frustrated Lewis Pair Mediated 1,2-Hydrocarbation of Alkynes.

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.

SUBMITTER: Fasano V

PROVIDER: S-EPMC5577509 | biostudies-literature | 2017 Jul

REPOSITORIES: biostudies-literature

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Frustrated Lewis Pair Mediated 1,2-Hydrocarbation of Alkynes.

Fasano Valerio V Curless Liam D LD Radcliffe James E JE Ingleson Michael J MJ

Angewandte Chemie (International ed. in English) 20170704 31

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 wit ...[more]

PMID: 28608991

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