Synthesis of Fluoroalkoxy Substituted Arylboronic Esters by Iridium-Catalyzed Aromatic C-H Borylation

Org Lett. 2015 Sep 4;17(17):4256-9. doi: 10.1021/acs.orglett.5b02050. Epub 2015 Aug 17.

Abstract

The preparation of fluoroalkoxy arylboronic esters by iridium-catalyzed aromatic C-H borylation is described. The fluoroalkoxy groups employed include trifluoromethoxy, difluoromethoxy, 1,1,2,2-tetrafluoroethoxy, and 2,2-difluoro-1,3-benzodioxole. The borylation reactions were carried out neat without the use of a glovebox or Schlenk line. The regioselectivities available through the iridium-catalyzed C-H borylation are complementary to those obtained by the electrophilic aromatic substitution reactions of fluoroalkoxy arenes. Fluoroalkoxy arylboronic esters can serve as versatile building blocks.

Publication types

  • Research Support, Non-U.S. Gov't