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Title: Synthesis of Fused Carbazoles by Gold-Catalyzed Tricyclization of Conjugated Diynes via Rearrangement of an N-Propargyl Group
Authors: Taguchi, Masamitsu
Tokimizu, Yusuke
Oishi, Shinya
Fujii, Nobutaka
Ohno, Hiroaki
Author's alias: 大石, 真也
藤井, 信孝
大野, 浩章
Issue Date: 18-Dec-2015
Publisher: American Chemical Society
Journal title: Organic Letters
Volume: 17
Issue: 24
Start page: 6250
End page: 6253
Abstract: Various N-propargylanilines bearing a conjugated diyne moiety at the 2-position were converted to tetracyclic fused carbazoles by treatment with a homogeneous gold(I) catalyst. This cascade reaction proceeds through indole formation with concomitant rearrangement of the N-propargyl group, intramolecular nucleophilic addition toward the resulting allene moiety, and subsequent hydroalkenylation. This transformation enables a one-pot synthesis of fused carbazoles from readily accessible substrates with 100% atom economy.
Rights: This document is the Accepted Manuscript version of a Published Work that appeared in final form in 'Organic Letters', copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.orglett.5b03254.
The full-text file will be made open to the public on 9 December 2016 in accordance with publisher's 'Terms and Conditions for Self-Archiving'.
This is not the published version. Please cite only the published version. この論文は出版社版でありません。引用の際には出版社版をご確認ご利用ください。
URI: http://hdl.handle.net/2433/241633
DOI(Published Version): 10.1021/acs.orglett.5b03254
PubMed ID: 26649487
Appears in Collections:Journal Articles

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