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

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...

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Bibliographic Details
Published in:Journal of organic chemistry 2021-08, Vol.86 (15), p.10067-10087
Main Authors: Shibata, Kouhei, Takao, Ken-ichi, Ogura, Akihiro
Format: Article
Language:English
Subjects:
Carbamates
Indoles
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Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.1c00820