C(sp2)–H Trifluoromethylation of enamides using TMSCF3: access to trifluoromethylated isoindolinones, isoquinolinones, 2-pyridinones and other heterocycles

Vinayak Krishnamurti; Socrates B. Munoz; Xanath Ispizua-Rodriguez; Jeffrey Vickerman; Thomas Mathew; G. K. Surya Prakash

doi:10.1039/C8CC04907F

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C(sp²)–H Trifluoromethylation of enamides using TMSCF₃: access to trifluoromethylated isoindolinones, isoquinolinones, 2-pyridinones and other heterocycles†

Vinayak Krishnamurti,‡^a Socrates B. Munoz,

‡^a Xanath Ispizua-Rodriguez,^a Jeffrey Vickerman,^a Thomas Mathew

^a and G. K. Surya Prakash

*^a

Author affiliations

* Corresponding authors

^a Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, Los Angeles, California, USA
E-mail: gprakash@usc.edu

Abstract

A method for the direct C(sp²)–H trifluoromethylation of enamides, including biologically relevant isoindolinones, isoquinolinones and 2-pyridinones using TMSCF₃ under oxidative conditions is presented. The protocol is convenient, operationally simple and exhibits high tolerance across a multitude of relevant handles and functional groups.

This article is part of the themed collection: Fluorine Chemistry

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Article information

DOI: https://doi.org/10.1039/C8CC04907F
Article type: Communication
Submitted: 20 iyn 2018
Accepted: 21 avq 2018
First published: 29 avq 2018

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Chem. Commun., 2018,54, 10574-10577

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C(sp²)–H Trifluoromethylation of enamides using TMSCF₃: access to trifluoromethylated isoindolinones, isoquinolinones, 2-pyridinones and other heterocycles

V. Krishnamurti, S. B. Munoz, X. Ispizua-Rodriguez, J. Vickerman, T. Mathew and G. K. Surya Prakash, Chem. Commun., 2018, 54, 10574 DOI: 10.1039/C8CC04907F

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