☆ 4.8 Article

Co(III)-Catalyzed, Internal and Terminal Alkyne-Compatible Synthesis of Indoles

ORGANIC LETTERS (2016)

Journal

ORGANIC LETTERS

Volume 18, Issue 15, Pages 3806-3809

Publisher

AMER CHEMICAL SOC

DOI: 10.1021/acs.orglett.6b01805

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Categories

Chemistry, Organic

Funding

National Natural Science Foundation of China [21425415, 21274058]
National Basic Research Program of China [2015CB856303]

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Abstract

A Co(III)-catalyzed, internal and terminal alkyne-compatible indole synthesis protocol is reported herein. The N-amino (hydrazine) group imparts distinct, diverse reactivity patterns for directed C-H functionalization/cyclization reactions. Notable synthetic features include regioselectivity for a meta-substituted arylhydrazine, regioselectivity for a chain-branched terminal alkyne, formal incorporation of an acetylenic unit through C2-desilylation On a C2-silylated indole derivative, formal inversion of regioselectivity through consecutive C3-derivatization and C2-desilylation processes, and formal bond migration for a linear-chain terminal alkyne.

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