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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.