Pd(II)-Catalyzed [4 + 2] Heterocyclization Sequence for Polyheterocycle Generation

A new Pd­(II)-catalyzed cascade sequence for the formation of polyheterocycles, from simple starting materials, is reported. The sequence is applicable to both indole and pyrrole substrates, and a range of substituents are tolerated. The reaction is thought to proceed by a Pd­(II)-catalyzed C–H acti...

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Bibliographic Details
Published in:Organic letters 2018-09, Vol.20 (18), p.5877-5880
Main Authors: Glaisyer, Elizabeth L, Watt, Michael S, Booker-Milburn, Kevin I
Format: Article
Language:English
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Summary:A new Pd­(II)-catalyzed cascade sequence for the formation of polyheterocycles, from simple starting materials, is reported. The sequence is applicable to both indole and pyrrole substrates, and a range of substituents are tolerated. The reaction is thought to proceed by a Pd­(II)-catalyzed C–H activated Heck reaction followed by a second Pd­(II)-catalyzed aza-Wacker reaction with two Cu­(II)-mediated Pd(0) turnovers per sequence. The sequence can be considered a formal [4 + 2] heterocyclization.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.8b02543