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

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.

SUBMITTER: Kirsch JK

PROVIDER: S-EPMC6375689 | biostudies-literature | 2018 Nov

REPOSITORIES: biostudies-literature

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

Kirsch Janelle K JK Manske Jenna L JL Wolfe John P JP

The Journal of organic chemistry 20181010 21

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 e ...[more]

PMID: 30351050

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