Issue 58, 2016

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

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

Supplementary files

Article information

Article type
Communication
Submitted
14 Qun 2016
Accepted
01 Nah 2016
First published
01 Nah 2016

Chem. Commun., 2016,52, 9052-9055

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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