Regioselective Synthesis of N-Heteroaromatic Trifluoromethoxy Compounds by Direct O-CF3 Bond Formation

Chemistry. 2016 Apr 4;22(15):5102-6. doi: 10.1002/chem.201505181. Epub 2016 Feb 25.

Abstract

The first one-step method for the synthesis of ortho-N-heteroaromatic trifluoromethoxy derivatives by site-specific O-CF3 bond formation using hydroxylated N-heterocycles and Togni's reagent is described. The approach enables the unprecedented syntheses of a wide range of six or five-membered N-heteroaromatic trifluoromethoxy compounds containing one or two heteroatoms from most commonly used hydroxylated N-heterocycles. Notable advantages of this method include its simplicity and mild conditions, avoidance of the need for metals or toxic reagents, and compatibility with a variety of functional groups. Furthermore, this method is especially suitable for the larger scale application.

Keywords: C−O bond formation; N-heterocycles; hypervalent iodine reagents; trifluoromethylation.

Publication types

  • Research Support, Non-U.S. Gov't