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Title: Gold(I)-Catalyzed Cascade Cyclization of Anilines with Diynes: Controllable Formation of Eight-Membered Ring-Fused Indoles and Propellane-Type Indolines
Authors: Yamaguchi, Ayuta
Inuki, Shinsuke  kyouindb  KAKEN_id  orcid (unconfirmed)
Tokimizu, Yusuke
Oishi, Shinya
Ohno, Hiroaki  kyouindb  KAKEN_id  orcid (unconfirmed)
Author's alias: 山口, 亞由太
井貫, 晋輔
大石, 真也
大野, 浩章
Issue Date: 21-Feb-2020
Publisher: NLM (Medline)
Journal title: The Journal of organic chemistry
Volume: 85
Issue: 4
Start page: 2543
End page: 2559
Abstract: Heterocycle-fused indoles or indolines are distributed widely in a variety of natural products, bioactive agents, and pharmaceuticals. Herein, we describe the development of gold-catalyzed cascade reactions of anilines with diynes to form eight-membered ring-fused indoles and propellane-type indolines, both of which proceed through an intramolecular 5-endo-dig hydroamination followed by an 8-endo-dig cycloisomerization. Controllable formation of eight-membered ring-fused indoles and propellane-type indolines was achieved through selection of the ligands and/or solvents. Protic solvents such as alcohols or IPr ligand favored the formation of eight-membered ring-fused indoles, whereas the use of Buchwald’s type ligands and/or nonpolar solvents gave propellane-type indoline predominantly. This reaction provides rapid access to two types of fused nitrogen heterocycles from simple aniline derivatives.
Rights: This document is the Accepted Manuscript version of a Published Work that appeared in final form in The Journal of organic chemistry, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see
The full-text file will be made open to the public on 8 January 2021 in accordance with publisher's 'Terms and Conditions for Self-Archiving'.
This is not the published version. Please cite only the published version.
DOI(Published Version): 10.1021/acs.joc.9b03256
PubMed ID: 31913037
Appears in Collections:Journal Articles

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