Synthesis of 2-acyl benzofurans and indoles based on nucleophile-intercepted Meyer–Schuster rearrangement of o-hydroxyphenyl and o-aminophenyl propargylic alcohols
Literature Information
Publication Date
2023-12-11
DOI
10.1039/D3QO01671D
Impact Factor
5.281
Authors
Zhao-Zhao Li, Si-Jing Jiang, Shu-Yun He, Yu-Ning Gao, Ming Bian, Hui-Yu Chen
View Original
Abstract
A metal-free synthetically useful catalytic approach for the preparation of 2-acyl benzofurans and indoles from easily accessible o-hydroxyphenyl and o-aminophenyl propargylic alcohols in the presence of pyridine N-oxide is disclosed. This protocol comprises the acid promoted formation of a carbocation and subsequent nucleophilic trapping by pyridine N-oxide, which leads to umpolung of the allenyl ether moiety. The following intramolecular attack at the umpolung allenyl carbon furnishes the final benzofurans and indoles via a nucleophile-intercepted Meyer–Schuster rearrangement.
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Source Journal
Organic Chemistry Frontiers
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7.8
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8.7%
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Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
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Molecular Formula:
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