Fluoroalkyl Amino Reagents for the Introduction of the Fluoro(trifluoromethoxy)methyl Group onto Arenes and Heterocycles

Org Lett. 2017 Sep 15;19(18):4960-4963. doi: 10.1021/acs.orglett.7b02444. Epub 2017 Sep 1.

Abstract

Fluoroalkyl amino reagents 1a and 2a have been developed from commercially available trifluoromethyl trifluorovinyl ether via a hydroamination reaction with diethylamine or dimethylamine. These reagents can be activated by treatment with a Lewis acid and subsequently used as a mono- or dielectrophile for the introduction of the fluoro(trifluoromethoxy)methyl group, either in Vilsmeier-type acylations of aromatic substrates or in the synthesis of fluorinated pyrazoles from CH-acidic substrates and of bis-fluorinated pyrazoles, all being important building blocks for medicinal and agricultural chemistry.

Publication types

  • Research Support, Non-U.S. Gov't