Iron-catalyzed, highly regioselective synthesis of α-aryl carboxylic acids from styrene derivatives and CO2

Mark D. Greenhalgh, Stephen P. Thomas*

*Corresponding author for this work

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

171 Citations (Scopus)

Abstract

The iron-catalyzed hydrocarboxylation of aryl alkenes has been developed using a highly active bench-stable iron(II) precatalyst to give α-aryl carboxylic acids in excellent yields and with near-perfect regioselectivity. Using just 1 mol % FeCl2, bis(imino)pyridine 6 (1 mol %), CO 2 (atmospheric pressure), and a hydride source (EtMgBr, 1.2 equiv), a range of sterically and electronically differentiated aryl alkenes were transformed to the corresponding α-aryl carboxylic acids (up to 96% isolated yield). The catalyst was found to be equally active with a loading of 0.1 mol %. Preliminary mechanistic investigations show that an iron-catalyzed hydrometalation is followed by transmetalation and reaction with the electrophile (CO2). © 2012 American Chemical Society.

Original languageEnglish
Pages (from-to)11900-11903
Number of pages4
JournalJournal of the American Chemical Society
Volume134
Issue number29
DOIs
Publication statusPublished - 25 Jul 2012

Structured keywords

  • BCS and TECS CDTs

Keywords

  • CROSS-COUPLING REACTIONS
  • H BOND ACTIVATION
  • GRIGNARD-REAGENTS
  • EXCHANGE-REACTION
  • OLEFIN-EXCHANGE
  • CARBON-DIOXIDE
  • COMPLEXES
  • HYDROSILYLATION
  • HYDROGENATION
  • ALKENES

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