Frustrated Lewis Pair Mediated 1,2‐Hydrocarbation of Alkynes | Zendy

Fasano Valerio | Zendy; Curless Liam D. | Zendy; Radcliffe James E. | Zendy; Ingleson Michael J. | Zendy

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Frustrated Lewis Pair Mediated 1,2‐Hydrocarbation of Alkynes

Author(s) -

Fasano Valerio,

Curless Liam D.,

Radcliffe James E.,

Ingleson Michael J.

Publication year - 2017

Publication title -

angewandte chemie

Language(s) - English

Resource type - Journals

eISSN - 1521-3757

pISSN - 0044-8249

DOI - 10.1002/ange.201705100

Subject(s) - alkyne , frustrated lewis pair , chemistry , intramolecular force , hydride , lewis acids and bases , hydroboration , stereochemistry , triple bond , medicinal chemistry , polymer chemistry , organic chemistry , catalysis , double bond , metal

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.

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