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A catalyst-free bis(triflyl)ethylation/benzannulation reaction: rapid access to carbazole-based superacidic carbon acids from alkynols

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Abstract

Carbazoles possessing Tf2CHCH2 groups were obtained by the reaction of 1-(indol-2-yl)but-3-yn-1-ols with in situ-generated Tf2C[double bond, length as m-dash]CH2 through vicinal difunctionalisation of the alkyne moiety, where the vinyl-type carbocation intermediate was selectively attacked by the indole moiety and not by the carbanion moiety.

Graphical abstract: A catalyst-free bis(triflyl)ethylation/benzannulation reaction: rapid access to carbazole-based superacidic carbon acids from alkynols

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Article information


Submitted
15 Nov 2019
Accepted
03 Jan 2020
First published
03 Jan 2020

This article is Open Access

Chem. Commun., 2020, Advance Article
Article type
Communication

A catalyst-free bis(triflyl)ethylation/benzannulation reaction: rapid access to carbazole-based superacidic carbon acids from alkynols

I. Martín-Mejías, C. Aragoncillo, H. Yanai, S. Hoshikawa, Y. Fujimoto, T. Matsumoto and P. Almendros, Chem. Commun., 2020, Advance Article , DOI: 10.1039/C9CC08930F

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