Pd‐Catalyzed Highly Regioselective N‐Acylation of Indoles with Difluorocarbene as a Carbonyl Source

An efficient one-pot protocol for the exclusively N-regioselective synthesis of N-benzoylindoles has been developed, employing difluorocarbene: (CF₂) as a carbonyl-bridging moiety to simultaneously forge one C─C bond, one C─N bond, and one C═O bond. This strategy not only extends the synthetic versatility of: CF₂ in carbonylative coupling but also provides an approach to accessing carbonylation products, which provides a practical strategy for constructing heterocyclic amide frameworks.

Abstract

A novel method has been developed for the exclusively N-regioselective synthesis of N-benzoylindoles, utilizing readily available aryl halides, indoles, and sodium difluorochloroacetate. The in situ-generated carbonyl group produced through difluorocarbene transfer serves as a bridging moiety that facilitates the simultaneous formation of one C─C bond, one C─N bond, and one C═O bond in this transformation.

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