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Issue 58, 2016
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Organic base-catalysed solvent-tuned chemoselective carbotrifluoromethylation and oxytrifluoromethylation of unactivated alkenes

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Abstract

An unprecedented and efficient organic base-catalysed highly chemoselective carbo- and oxytrifluoromethylation of unactivated alkenes with Togni's reagent was developed. The switchable chemoselectivity was tuned by simply changing the organic base catalyst and solvent. Mechanistic studies indicated that a radical cyclization pathway for carbotrifluoromethylation in DMSO and a carbocation pathway for oxytrifluoromethylation in DCE were probably involved.

Graphical abstract: Organic base-catalysed solvent-tuned chemoselective carbotrifluoromethylation and oxytrifluoromethylation of unactivated alkenes

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Publication details

The article was received on 14 Jan 2016, accepted on 01 Feb 2016 and first published on 01 Feb 2016


Article type: Communication
DOI: 10.1039/C6CC00364H
Citation: Chem. Commun., 2016,52, 9052-9055

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    Organic base-catalysed solvent-tuned chemoselective carbotrifluoromethylation and oxytrifluoromethylation of unactivated alkenes

    N. Yang, Z. Li, L. Ye, B. Tan and X. Liu, Chem. Commun., 2016, 52, 9052
    DOI: 10.1039/C6CC00364H

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