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Issue 9, 2018
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Direct C3-arylations of 2-indolylmethanols with tryptamines and tryptophols via an umpolung strategy

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Abstract

A Brønsted acid-catalyzed direct C3-arylation of 2-indolylmethanols with tryptamines and tryptophols has been established, leading to a series of potentially bioactive 2,3′-biindole derivatives with a broad substrate scope and generally good yields (38 examples, up to 96% yield). In this process, the reactivity of the C3-position of 2-indolylmethanol is switched from nucleophilic to electrophilic, which can serve as an umpolung strategy in indole chemistry. This protocol not only provides a new strategy for accessing structurally diversified 2,3′-biindolyl frameworks, but also satisfies the requirement of green chemistry.

Graphical abstract: Direct C3-arylations of 2-indolylmethanols with tryptamines and tryptophols via an umpolung strategy

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Supplementary files

Article information


Submitted
26 Dec 2017
Accepted
31 Jan 2018
First published
01 Feb 2018

Org. Biomol. Chem., 2018,16, 1536-1542
Article type
Paper

Direct C3-arylations of 2-indolylmethanols with tryptamines and tryptophols via an umpolung strategy

Y. Wan, H. Wang, M. Xu, G. Mei and F. Shi, Org. Biomol. Chem., 2018, 16, 1536 DOI: 10.1039/C7OB03182C

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