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Updated: Feb 14, 2026

Light-driven Enzymatic Decarboxylation
Published on: May 22, 2016
Rapid Access to Ortho-Alkylated Vinylarenes from Aromatic Acids by Dearomatization and Tandem Decarboxylative C-H
Hung-Chang Tsai1, Yen-Hsiang Huang1, Chih-Ming Chou1
1Department of Applied Chemistry, National University of Kaohsiung , 700 Kaohsiung University Road, Nanzih District, Kaohsiung 81148, Taiwan.
Abstract:
A two-step straightforward method for the preparation of ortho-alkylated vinylarenes from readily available benzoic acids is described. The synthetic route involves the dearomatization of benzoic acids by Birch reduction providing alkylated cyclohexa-2,5-dienyl-1-carboxylic acids. The diene subsequently undergoes a decarboxylative C-H olefination followed by rearomatization to deliver ortho-alkylated vinylarene. Mechanistic studies suggest that a Pd/Ag bimetallic catalytic system is important in the tandem decarboxylative C-H olefination/rearomatization step.
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