A radical-initiated fragmentary rearrangement cascade of ene-ynamides to [1,2]-annulated indoles via site-selective cyclization

Sifan Li, Yu Wang, Zibo Wu, weilang shi, Yibo lei, Paul Davies, Wei Shu

Research output: Contribution to journalLetterpeer-review

Abstract

Straightforward access to [1,2]-annulated indoles, key substructures in natural products, is highly desirable yet challenging. Herein, a radical triggered fragmentary cyclization cascade reaction of ene-ynamides is presented, providing a rapid access into [1,2]-annulated indoles by an intermolecular radical addition, intramolecular cyclization, desulfonylative aryl migration, and site-selective C(sp2)-N cyclization sequence. DFT calculations support oxidation of N-centered radical species to cations prior to the C–N bond formation, followed by an unusual aza-Nazarov cyclization.
Original languageEnglish
JournalOrganic Letters
Early online date28 Aug 2021
DOIs
Publication statusE-pub ahead of print - 28 Aug 2021

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