The Journal of organic chemistry

A highly selective tandem cross-coupling of gem-dihaloolefins for a modular, efficient synthesis of highly functionalized indoles

YQ Fang, M Lautens

Index: Fang, Yuan-Qing; Lautens, Mark Journal of Organic Chemistry, 2008 , vol. 73, # 2 p. 538 - 549

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Citation Number: 138

Abstract

A highly efficient method of indole synthesis using gem-dihalovinylaniline substrates and an organoboron reagent was developed via a Pd-catalyzed tandem intramolecular amination and an intermolecular Suzuki coupling. Aryl, alkenyl, and alkyl boron reagents are all successfully employed, making for a versatile modular approach. The reaction tolerates a variety of substitution patterns on the aniline leading to indoles with group at C2-C7. The ...

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