Diaryliodonium Salt-Based Synthesis of N-Alkoxyindolines and Further Insights into the Ishikawa Indole Synthesis

Kouhei Shibata, Ken Ichi Takao, Akihiro Ogura

Research output: Contribution to journalArticlepeer-review

Abstract

A diaryliodonium salt-based strategy enabled the first systematic synthesis of rarely accessible N-alkoxyindolines. Mechanistic analyses suggested that the reaction likely involves reductive elimination of iodobenzene from iodaoxazepine via a four-membered transition state, followed by Meisenheimer rearrangement. Substrates with N-carbamate protection afforded indole in a manner similar to that of the Ishikawa indole synthesis. Preinstallation of a stannyl group as an iodonium salt precursor greatly expanded the substrate scope, and further mechanistic insights are discussed.

Original languageEnglish
Pages (from-to)10067-10087
Number of pages21
JournalJournal of Organic Chemistry
Volume86
Issue number15
DOIs
Publication statusPublished - 2021 Aug 6

ASJC Scopus subject areas

  • Organic Chemistry

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