Issue 47, 2018

Copper-mediated 1,2-bis(trifluoromethylation) of arynes


We herein describe an unprecedented 1,2-bis(trifluoromethylation) of arynes with [CuCF3] in the presence of an oxidant DDQ. The method allows the rapid construction of a new class of 1,2-bis(trifluoromethyl)arenes in one-step from aryne precursors under mild conditions. Its synthetic utility has been demonstrated in the preparation of bis(trifluoromethylated) molecules with potential pharmaceutical and materials science applications. Mechanistic studies indicated the presence of an o-trifluoromethyl aryl radical intermediate via CF3 group transfer from [CuCF3] to the aryne.

Graphical abstract: Copper-mediated 1,2-bis(trifluoromethylation) of arynes

Supplementary files

Article information

Article type
Edge Article
22 Aug 2018
20 Sep 2018
First published
21 Sep 2018
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2018,9, 8871-8875

Copper-mediated 1,2-bis(trifluoromethylation) of arynes

X. Yang and G. C. Tsui, Chem. Sci., 2018, 9, 8871 DOI: 10.1039/C8SC03754J

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

Read more about how to correctly acknowledge RSC content.

Social activity