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. 2018 Nov 2;83(21):13568-13573.
doi: 10.1021/acs.joc.8b02165. Epub 2018 Oct 10.

Pd-Catalyzed Alkene Carboheteroarylation Reactions for the Synthesis of 3-Cyclopentylindole Derivatives

Janelle K Kirsch  1 , Jenna L Manske  1 , John P Wolfe  1
Affiliations

Pd-Catalyzed Alkene Carboheteroarylation Reactions for the Synthesis of 3-Cyclopentylindole Derivatives

Janelle K Kirsch et al. J Org Chem. .

Abstract

The Pd-catalyzed alkene carboheteroarylation of aryl and alkenyl triflate electrophiles bearing pendant alkenes with heteroaromatic nucleophiles affords substituted carbocycles with 3-indolyl or 3-pyrrolyl groups. The products are obtained in moderate to good yields, and the use of alkenyl triflate substrates produces products with high diastereoselectivities. The transformation is believed to proceed via a Friedel-Crafts-like reaction between the heteroaromatic nucleophile and an intermediate electrophilic palladium complex.

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Conflict of interest statement

The authors declare no competing financial interests.

Figures

Scheme 1.
Scheme 1.
Reactions of Aryl Triflatesa,b
Scheme 2.
Scheme 2.
Reactions of Alkenyl Triflatesa,b
Scheme 3.
Scheme 3.
Proposed Catalytic Cycle
None
None
None
See this image and copyright information in PMC

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