Frustrated Lewis Pair Mediated 1,2-Hydrocarbation of Alkynes

Valerio Fasano, Liam D. Curless, James E. Radcliffe, Michael J. Ingleson*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

12 Citations (Scopus)
144 Downloads (Pure)

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.

Original languageEnglish
Pages (from-to)9202-9206
Number of pages5
JournalAngewandte Chemie - International Edition
Volume56
Issue number31
Early online date4 Jul 2017
DOIs
Publication statusPublished - 24 Jul 2017

Keywords

  • 1,2-hydrocarbation
  • alkynes
  • carbocations
  • frustrated Lewis pairs
  • hydride transfer

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