Boron-Mediated Regioselective Aromatic C−H Functionalization via an Aryl BF2 Complex
Journal article, 2023

An efficient regioselective functionalization of 2-aryl-heteroarenes and aryl aldehydes via an azaaryl BF2 complex has been developed. Mechanistically the reaction comprises fluoride to bromide ligand exchange on an aryl boron species and consecutive C−B bond cleavage to deliver a broad range of functionalized products. The reaction is high yielding, has a broad substrate scope where several different heteroarenes can be functionalized with chloro, bromo, iodo, hydroxyl, amine and BF2 in a highly regioselective fashion. The method can be applied for late-stage functionalization or for rapid skeleton remodeling with for instance cross-couplings.

BBr 3

aryl-aldehydes

N-heterocycles

Selectfluor

regioselective

ortho C−H halogenation

Author

Ganesh H. Shinde

University of Gothenburg

Henrik Sundén

Chalmers, Chemistry and Chemical Engineering, Chemistry and Biochemistry

University of Gothenburg

Chemistry - A European Journal

0947-6539 (ISSN) 1521-3765 (eISSN)

Vol. 29 1016 e202203505

Subject Categories

Theoretical Chemistry

Biocatalysis and Enzyme Technology

Organic Chemistry

DOI

10.1002/chem.202203505

PubMed

36383388

More information

Latest update

3/15/2023