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Palladium-catalyzed carbonylation of benzyl alcohol and its analogs promoted by HI in aqueous systems

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
38
Issue
21
Identifiers
DOI: 10.1016/s0040-4039(97)00744-2

Abstract

Abstract Carbonylation of benzyl alcohol catalyzed by a palladium(0) complex and promoted by hydrogen iodide gives phenylacetic acid in excellent yields in aqueous systems. The catalysis is proposed to proceed through a benzylpalladium species formed by the oxidative addition of benzyl iodide, produced in situ by the interaction of benzyl alcohol with HI, to a Pd(0) species. Application of the carbonylation process to other arylmethanol analogs provided convenient means to prepare 3-isochromanone, 1,4-benzenediacetic acid, 2-hydroxybenzeneacetic acid and 2-naphthaleneacetic acid.

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