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 language | English |
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Pages (from-to) | 11900-11903 |
Number of pages | 4 |
Journal | Journal of the American Chemical Society |
Volume | 134 |
Issue number | 29 |
DOIs | |
Publication status | Published - 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