Copper-catalyzed [1,3]-alkoxy rearrangement for the selective synthesis of polycyclic ortho-aminoarenol derivatives

文献信息

发布日期 2021-09-18

DOI 10.1039/D1QO01189H

影响因子 5.281

作者

Itaru Nakamura, Satoru Nozawa, Yasuhiro Ishida, Ichiro Muranushi, Alexandra Mayerweg, Masahiro Terada

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摘要

Copper-catalyzed [1,3]-alkoxy rearrangement reactions of polycyclic arenes, such as naphthalenes and phenanthrenes, proceeded efficiently to afford the corresponding ortho-aminoarenol derivatives in good to excellent yields with excellent ortho-selectivity. Through appropriate choice of an N-heterocyclic carbene (NHC) ligand, the reactions are applicable to not only a methoxy group but also readily deprotectable p-nitrobenzyloxy and methoxymethoxy groups. Moreover, the rearrangement of the N-methoxyamino group on the benzene ring of indoles proceeded efficiently, affording the corresponding functionalized indoles in a site-selective manner.

期刊推荐

Pure and Applied Chemistry

Pharmacological Reviews

Journal of Organometallic Chemistry

Nature

Molecular Pharmacology

Proceedings of the National Academy of Sciences of the United States of America

Journal of Heterocyclic Chemistry

Organic Preparations and Procedures International

Science Progress

Journal of Catalysis

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

Copper-catalyzed [1,3]-alkoxy rearrangement for the selective synthesis of polycyclic ortho-aminoarenol derivatives

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