Metal‐Free Dehydrogenative Diels–Alder Reactions of 2‐Methyl‐3‐Alkylindoles with Dienophiles: Rapid Access to Tetrahydrocarbazoles, Carbazoles, and Heteroacenes | Zendy

Zhou Liejin | Zendy; Xu Bing | Zendy; Zhang Junliang | Zendy

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Metal‐Free Dehydrogenative Diels–Alder Reactions of 2‐Methyl‐3‐Alkylindoles with Dienophiles: Rapid Access to Tetrahydrocarbazoles, Carbazoles, and Heteroacenes

Author(s) -

Zhou Liejin,

Xu Bing,

Zhang Junliang

Publication year - 2015

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.201503549

Subject(s) - chemistry , combinatorial chemistry , metal , organic chemistry

An unprecedented strategy for in situ generation of indole‐based ortho ‐quinodimethanes ( o QDMs) from 2‐methyl‐3‐alkylmethylindoles by either a metal‐free DDQ‐ or BQ‐mediated dehydrogenative process was developed. These o QDMs were trapped by electron‐deficient dienophiles to provide a facile approach to synthetically valuable tetrahydrocarbazoles, carbazoles, and hetereoacenes. The salient features of this transformation include direct C(sp 3 )H bond functionalizations, readily available starting materials, metal‐free conditions, high efficiency, operational simplicity, and ease of scale‐up.

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