Indium(iii) catalyzed reactions of vinyl azides and indoles

Atul A. More, Alex M. Szpilman

Research output: Contribution to journalArticlepeer-review

14 Scopus citations

Abstract

Indium trichloride catalyzes the reaction of vinyl azides with unfunctionalized indoles to give vinyl indoles. This is the first example of displacement of the azide group by a carbon nucleophile while preserving the vinyl function. The protocol employs very mild reaction conditions and offers excellent yields of diverse 3-vinyl indoles. It is amenable to gram scale. Access to a library of 3,3′-bis(indolyl)methanes through condensation of vinyl azides with 2 equiv of an indole is demonstrated.

Original languageEnglish
Pages (from-to)3759-3764
Number of pages6
JournalOrganic Letters
Volume22
Issue number10
DOIs
StatePublished - 15 May 2020

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