Synthesis of fluoroalkoxy substituted aryl boronic esters by iridium catalyzed aromatic C-H borylation

F. Batool, S. Parveen, A.H. Emwas, S. Sioud, X. Gao, M.A. Munawar, G.A. Chotana
Organic Letters, 17(17) pp. 4256-4259, (2015)

Synthesis of fluoroalkoxy substituted aryl boronic esters by iridium catalyzed aromatic C-H borylation

Keywords

Arylboronic esters, CH borylation

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.

Code

DOI: 10.1021/acs.orglett.5b02050

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