Boron-Mediated Regioselective Aromatic C-H Functionalization via an Aryl BF2 Complex.

Shinde GH, Sundén H

Chemistry 29 (10) e202203505 [2023-02-16; online 2022-12-23]

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.

Swedish NMR Centre (SNC) [Service]

PubMed 36383388

DOI 10.1002/chem.202203505

Crossref 10.1002/chem.202203505

Publications 9.5.0