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Org Lett. 2019 Mar 22. doi: 10.1021/acs.orglett.9b00307. [Epub ahead of print]

Rhodium-Catalyzed Coupling-Cyclization of Alkenyldiazoacetates with o-Alkenyl Arylisocyanides: A General Route to Carbazoles.

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1
Jilin Province Key Laboratory of Organic Functional Molecular Design & Synthesis, Faculty of Chemistry , Northeast Normal University , Changchun 130024 , China.

Abstract

A rhodium-catalyzed coupling-cyclization reaction of alkenyldiazoacetates with o-alkenyl arylisocyanides has been developed. In this reaction, the highly reactive alkenylketenimine intermediates generated by coupling reaction of alkenyldiazoacetates with o-alkenyl arylisocyanides undergo intramolecular [4 + 2] cycloaddition and provide a novel, highly efficient method for the one-step synthesis of carbazoles by formation of three new bonds and two rings from readily available acyclic starting materials.

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