Iron-Catalyzed, Highly Regioselective Synthesis of α-Aryl Carboxylic Acids from Styrene Derivatives and CO₂

Mark D. Greenhalgh and Stephen P. Thomas*

*School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, United Kingdom, Email: stephen.thomased.ac.uk

M. D. Greenhalgh, S. P. Thomas, J. Am. Chem. Soc., 2012, 134, 11900-11903.

DOI: 10.1021/ja3045053

Abstract

Hydrocarboxylation of aryl alkenes in the presence of FeCl₂ as precatalyst, bis(imino)pyridine as ligand, an atmospheric pressure of CO₂, and EtMgBr as a hydride source gives α-aryl carboxylic acids in excellent yields and with near-perfect regioselectivity. Various, electronically differentiated aryl alkenes were transformed to the corresponding α-aryl carboxylic acids in very good isolated yield.

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Key Words

Hydrocarboxylations

ID: J48-Y2012-2370

Iron-Catalyzed, Highly Regioselective Synthesis of α-Aryl Carboxylic Acids from Styrene Derivatives and CO2

Mark D. Greenhalgh and Stephen P. Thomas*

Iron-Catalyzed, Highly Regioselective Synthesis of α-Aryl Carboxylic Acids from Styrene Derivatives and CO₂