Co(III)-Catalyzed, Internal and Terminal Alkyne-Compatible Synthesis of Indoles
Shuguang Zhou1, Jinhu Wang1, Lili Wang1
1Department of Polymer Science and Engineering, School of Chemistry and Chemical Engineering, State Key Laboratory of Coordination Chemistry, Nanjing National Laboratory of Microstructures, Nanjing University , Nanjing 210093, China.
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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