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Issue 77, 2018
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Synthesis of phthalic acid derivatives via Pd-catalyzed alkoxycarbonylation of aromatic C–H bonds with alkyl chloroformates

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Abstract

A Pd(II)-catalyzed alkoxycarbonylation of aromatic C–H bonds with alkyl chloroformates has been developed. A broad range of benzamides and alkyl chloroformates are compatible with this protocol. The reaction is operationally simple and scalable. The direct group could be readily removed to access substituted phthalic acid esters (PAEs), 1,2-dibenzyl alcohols and phthalamides. Besides alkoxycarbonylation of benzamide β-C–H bonds, γ-alkoxycarbonylation of 2-phenylacetamide is also feasible.

Graphical abstract: Synthesis of phthalic acid derivatives via Pd-catalyzed alkoxycarbonylation of aromatic C–H bonds with alkyl chloroformates

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Supplementary files

Article information


Submitted
15 Aug 2018
Accepted
03 Sep 2018
First published
03 Sep 2018

Chem. Commun., 2018,54, 10859-10862
Article type
Communication

Synthesis of phthalic acid derivatives via Pd-catalyzed alkoxycarbonylation of aromatic C–H bonds with alkyl chloroformates

G. Liao, H. Chen and B. Shi, Chem. Commun., 2018, 54, 10859 DOI: 10.1039/C8CC06663A

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