Issue 10, 2015

Cu-Mediated 2,2,2-trifluoroethylation of terminal alkynes using 1,1-dichloro-2,2,2-trifluoroethane (HCFC-123)

Abstract

The title reaction provides a novel utilization of ozone-depleting/global-warming HCFCs as a new carbon–carbon cross-coupling model of various terminal alkynes by activating two inert C–Cl bonds successively. This protocol provided trifluoroethylated alkynes efficiently under mild reaction conditions and was compatible with a broad range of functional groups. An example of the synthesis of a terbinafine analogue is shown. Some mechanistic experiments including deuterated reagents and radical/SET inhibitors are described.

Graphical abstract: Cu-Mediated 2,2,2-trifluoroethylation of terminal alkynes using 1,1-dichloro-2,2,2-trifluoroethane (HCFC-123)

Supplementary files

Article information

Article type
Research Article
Submitted
02 iyl 2015
Accepted
13 avq 2015
First published
14 avq 2015

Org. Chem. Front., 2015,2, 1379-1387

Cu-Mediated 2,2,2-trifluoroethylation of terminal alkynes using 1,1-dichloro-2,2,2-trifluoroethane (HCFC-123)

E. Han, Y. Sun, Q. Shen, Q. Chen, Y. Guo and Y. Huang, Org. Chem. Front., 2015, 2, 1379 DOI: 10.1039/C5QO00210A

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