Frustrated Lewis Pair mediated 1,2-hydrocarbation of alkynes

Valerio Fasano, Liam Curless, James Radcliffe, Michael Ingleson

    Research output: Contribution to journalArticlepeer-review


    Frustrated Lewis pair (FLP) chemistry enables a rare example of alkyne 1,2-hydrocarbation to be achieved using N-Me-acridinium salts as the carbon Lewis acid. This 1,2-hydrocarbation process does not proceed via a concerted mechanism as per alkyne syn-hydroboration, or via an intramolecular 1,3-hydride migration as operating in the only other reported alkyne 1,2-hydrocarbation reaction. Instead, in this work alkyne 1,2-hydrocarbation proceeds by a novel mechanism involving alkyne dehydrocarbation using a carbon Lewis acid based FLP to form the new C-C bond. Subsequently, intermolecular hydride transfer proceeds, with the Lewis acid component of the FLP acting as a hydride shuttle that enables alkyne 1,2-hydrocarbation.
    Original languageEnglish
    JournalAngewandte Chemie - International Edition
    Early online date13 Jun 2017
    Publication statusPublished - 2017


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