Synthesis of 2-acyl benzofurans and indoles based on nucleophile-intercepted Meyer–Schuster rearrangement of o-hydroxyphenyl and o-aminophenyl propargylic alcohols

文献信息

发布日期 2023-12-11

DOI 10.1039/D3QO01671D

影响因子 5.281

作者

Zhao-Zhao Li, Si-Jing Jiang, Shu-Yun He, Yu-Ning Gao, Ming Bian, Hui-Yu Chen

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摘要

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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来源期刊

Organic Chemistry Frontiers

CiteScore: 7.8

自引率: 8.7%

年发文量: 724

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

Synthesis of 2-acyl benzofurans and indoles based on nucleophile-intercepted Meyer–Schuster rearrangement of o-hydroxyphenyl and o-aminophenyl propargylic alcohols

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Organic Chemistry Frontiers

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