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Synthesis of 2,3-Disubstituted Indoles by Nickel(0)-Catalyzed Migratory Cycloisomerization of o-Alkynylanilides

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Title: Synthesis of 2,3-Disubstituted Indoles by Nickel(0)-Catalyzed Migratory Cycloisomerization of o-Alkynylanilides
Authors: Koshiba, Mikiko Browse this author
Furuki, Yuto Browse this author
Morisaki, Kazuhiro Browse this author
Doi, Ryohei Browse this author
Sato, Yoshihiro Browse this author →KAKEN DB
Keywords: Cycloisomerization
Indole
Migration
NHC
Nickel
Issue Date: 5-Jun-2023
Publisher: Wiley-Blackwell
Journal Title: Asian journal of organic chemistry
Volume: 12
Issue: 7
Start Page: e202300272
Publisher DOI: 10.1002/ajoc.202300272
Abstract: We herein report a nickel-catalyzed migratory cycloisomerization of o-alkynylanilides, giving 2,3-disubstituted indoles in good yields. The cyclization proceeded via acyl transfer on the nitrogen atom of the substrate to C3-position in the product, and an N-heterocyclic carbene (NHC) ligand such as ICy or SICy was found to be suitable in this reaction. It was thought that the reaction proceeds via an aza-nickelcyclepentene intermediate formed from alkyne and the C=O bond of the amide moiety in o-alkynylanilides.
Rights: This is the pre-peer reviewed version of the following article: https://onlinelibrary.wiley.com/doi/10.1002/ajoc.202300272, which has been published in final form at 10.1002/ajoc.202300272. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions.
Type: article (author version)
URI: http://hdl.handle.net/2115/92586
Appears in Collections:薬学研究院 (Faculty of Pharmaceutical Sciences) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

Submitter: 佐藤 美洋

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