Issue 12, 2020
From the journal:

Chemical Communications

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

Irene Martín-Mejías,a   Cristina Aragoncillo, ORCID logo b   Hikaru Yanai, ORCID logo *c   Shoki Hoshikawa, ORCID logo c   Yuuki Fujimoto, ORCID logo c   Takashi Matsumotoc  and  Pedro Almendros ORCID logo *a  

* Corresponding authors

a Instituto de Química Orgánica General, IQOG-CSIC, Juan de la Cierva 3, 28006-Madrid, Spain
E-mail: palmendros@iqog.csic.es

b Grupo de Lactamas y Heterociclos Bioactivos, Departamento de Química Orgánica, Unidad Asociada al CSIC, Facultad de Química, Universidad Complutense de Madrid, 28040-Madrid, Spain

c School of Pharmacy, Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan
E-mail: yanai@toyaku.ac.jp

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

DOI
https://doi.org/10.1039/C9CC08930F
Article type
Communication
Submitted
15 Nov 2019
Accepted
03 Jan 2020
First published
03 Jan 2020
This article is Open Access
Creative Commons BY-NC license

Chem. Commun., 2020,56, 1795-1798

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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, 56, 1795 DOI: 10.1039/C9CC08930F

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