Oxidant-Free C(sp2)–H Functionalization/C–O Bond Formation: A Kolbe Oxidative Cyclization Process

An anodic oxidation/cyclization of 2-arylbenzoic acids for the synthesis of dibenzopyranones has been developed. The reaction proceeds at room temperature with no oxidant or electrolyte required and exhibits a high atom economy with H2 being the only byproduct. A series of dibenzopyranones was obtai...

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Published inJournal of organic chemistry Vol. 83; no. 6; pp. 3200 - 3207
Main Authors Zhang, Lei, Zhang, Zhenxing, Hong, Junting, Yu, Jian, Zhang, Jianning, Mo, Fanyang
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 16.03.2018
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
DEHYDROGENATIVE LACTONIZATION
LACTONES
CATALYZED C(SP)-H
GREEN SYNTHESIS
BENZOXAZOLES
METAL
ELECTROOXIDATIVE CYCLIZATION
RADICAL REACTIONS
ELECTROCHEMICAL SYNTHESIS
CARBOXYLIC-ACIDS
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Summary:An anodic oxidation/cyclization of 2-arylbenzoic acids for the synthesis of dibenzopyranones has been developed. The reaction proceeds at room temperature with no oxidant or electrolyte required and exhibits a high atom economy with H2 being the only byproduct. A series of dibenzopyranones was obtained in good to excellent yields. Urolithins A, B, and C are formally synthesized by adopting this method as a key step to demonstrate its synthetic utility.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.8b00089