A Rh(II)/phosphoric acid co-catalyzed three-component reaction of diazo-ketones with alcohols and azonaphthalenes: access to indole derivatives via a formal [3 + 2]-cycloaddition

Xinru Yin; Aimin Xu; Jidi Hu; Ming Bao; Wenhao Hu; Yu Qian

doi:10.1039/D0OB02189J

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A Rh(ii)/phosphoric acid co-catalyzed three-component reaction of diazo-ketones with alcohols and azonaphthalenes: access to indole derivatives via a formal [3 + 2]-cycloaddition†

Xinru Yin,^a Aimin Xu,^a Jidi Hu,^a Ming Bao,^a Wenhao Hu*^a and Yu Qian

*^a

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* Corresponding authors

^a Guangdong Provincial Key Laboratory of Chiral Molecule and Drug Discovery, School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou 510006, China
E-mail: huwh9@mail.sysu.edu.cn, qianyu5@mail.sysu.edu.cn

Abstract

A novel dearomatization/rearomatization/cyclization oxonium ylide trapping process is well developed via a dirhodium(II) acetate and phosphoric acid cooperatively catalyzed multi-component reaction of diazo-ketones with alcohols and azonaphthalenes. This protocol provides an efficient route to synthesize N-substituted 1-amino-indole derivatives in good yield under mild reaction conditions.

This article is part of the themed collection: Synthetic methodology in OBC

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DOI: https://doi.org/10.1039/D0OB02189J
Article type: Communication
Submitted: 03 Nov 2020
Accepted: 27 Nov 2020
First published: 27 Nov 2020

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Org. Biomol. Chem., 2020,18, 9805-9809

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A Rh(II)/phosphoric acid co-catalyzed three-component reaction of diazo-ketones with alcohols and azonaphthalenes: access to indole derivatives via a formal [3 + 2]-cycloaddition

X. Yin, A. Xu, J. Hu, M. Bao, W. Hu and Y. Qian, Org. Biomol. Chem., 2020, 18, 9805 DOI: 10.1039/D0OB02189J

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Organic & Biomolecular Chemistry

A Rh(ii)/phosphoric acid co-catalyzed three-component reaction of diazo-ketones with alcohols and azonaphthalenes: access to indole derivatives via a formal [3 + 2]-cycloaddition†

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A Rh(II)/phosphoric acid co-catalyzed three-component reaction of diazo-ketones with alcohols and azonaphthalenes: access to indole derivatives via a formal [3 + 2]-cycloaddition

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