Oxidative Route to Indoles via Intramolecular Amino-Hydroxylation of o-Allenyl Anilines

Nicholas R. Lauta, Ryan E. Williams, David T. Smith, Vlad K. Kumirov, Jon T. Njardarson

Research output: Contribution to journalArticlepeer-review

Abstract

A new intramolecular oxidative amino-hydroxylation of o-allenyl anilines is reported. Treatment of carbamate-protected anilines with lead(IV) carboxylates in dichloromethane at room temperature results in facile tandem C-N (allene cyclization) and C-O bond formation (carboxylate trapping) to form indole products. Detailed reaction scope, mechanistic and kinetic studies suggest a reaction pathway involving an initial Wessely dearomatization step followed by cyclization and rearomatization.

Original languageEnglish (US)
Pages (from-to)10713-10723
Number of pages11
JournalJournal of Organic Chemistry
Volume86
Issue number15
DOIs
StatePublished - Aug 6 2021

ASJC Scopus subject areas

  • Organic Chemistry

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