Issue 20, 2015

Simultaneous introduction of trifluoromethyl and λ6-pentafluorosulfanyl substituents using F5S–C[triple bond, length as m-dash]C–CF3 as a dienophile

Abstract

F5S–C[triple bond, length as m-dash]C–CF3 can be easily prepared in high yields in two steps from 3,3,3-trifluoropropyne. It is a powerful, versatile dienophile in Diels–Alder reactions. Reactions at room temperature provide the corresponding products in up to quantitative yields allowing the introduction of the pentafluorosulfanyl group and trifluoromethyl group at the 1,2 position.

Graphical abstract: Simultaneous introduction of trifluoromethyl and λ6-pentafluorosulfanyl substituents using F5S–C [[triple bond, length as m-dash]] C–CF3 as a dienophile

Supplementary files

Article information

Article type
Communication
Submitted
27 Mar 2015
Accepted
15 Apr 2015
First published
15 Apr 2015
This article is Open Access
Creative Commons BY-NC license

Org. Biomol. Chem., 2015,13, 5625-5628

Simultaneous introduction of trifluoromethyl and λ6-pentafluorosulfanyl substituents using F5S–C[triple bond, length as m-dash]C–CF3 as a dienophile

B. Duda and D. Lentz, Org. Biomol. Chem., 2015, 13, 5625 DOI: 10.1039/C5OB00610D

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