Synthesis of 3,3′‐Disubstituted Isobenzofuran‐1(3H)‐Ones via Cs0.5H2.5PW12O40‐Catalyzed Difunctionalization of Carbonyls

We reported a method for the synthesis of 3,3′‐disubstituted isobenzofuran‐1(3H)‐ones via the carbonyl difunctionalization of 2‐acylbenzoic acids. A range of nucleophiles was reacted with 2‐acylbenzoic acids to furnish the functionalized isobenzofuran‐1(3H)‐ones with the factual yield range of 61–96...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2022-04, Vol.364 (8), p.1460-1464
Main Authors: Liu, Yu‐Feng, Cao, Gang‐Ming, Chen, Lei, Li, Ke, Lin, Xiao‐Ling, Xu, Xin‐Xin, Le, Zhang‐Gao, Yang, Guo‐Ping
Format: Article
Language:English
Subjects:
2-acylbenzoic acids
3,3′-disubstituted isobenzofuran-1(3H)-ones
Carbonyls
Chemical synthesis
difunctionalization
diphenylphosphine oxide
Functional groups
Nucleophiles
polyoxometalates
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Summary:We reported a method for the synthesis of 3,3′‐disubstituted isobenzofuran‐1(3H)‐ones via the carbonyl difunctionalization of 2‐acylbenzoic acids. A range of nucleophiles was reacted with 2‐acylbenzoic acids to furnish the functionalized isobenzofuran‐1(3H)‐ones with the factual yield range of 61–96%. The reaction uses Cs0.5H2.5PW12O40 as a catalyst and produces water as the sole by‐product. Various functional groups could be introduced to the isobenzofuran‐1(3H)‐one skeletons via the C−P/C−N/C−O/C−C bond formation, which would provide opportunities for the synthesis of potential biologically active molecules. Based on the preliminary experiments, a plausible mechanism is proposed.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202200081