title: Rhodium-catalyzed borylation of aryl 2-pyridyl ethers through cleavage of the carbon-oxygen bond: borylative removal of the directing group.
abstract: The rhodium-catalyzed reaction of aryl 2-pyridyl ethers with a diboron reagent results in the formation of arylboronic acid derivatives via activation of the C(aryl)-O bonds. The straightforward synthesis of 1,2-disubstituted arenes was enabled through catalytic ortho C-H bond functionalization directed by the 2-pyridyloxy group followed by substitution of this group with a boryl group. Several control experiments revealed that the presence of a sp(2) nitrogen atom at the 2-position of the substrate and the use of a boron-based reagent were crucial for the activation of the relatively inert C(aryl)-O bond of aryl 2-pyridyl ethers.
authors.affiliation: Department of Applied Chemistry, Faculty of Engineering, Osaka University , Suita, Osaka 565-0871, Japan.
authors.forename: Hirotaka
authors.initials: H
authors.lastname: Kinuta
authors.forename: Mamoru
authors.initials: M
authors.lastname: Tobisu
authors.forename: Naoto
authors.initials: N
authors.lastname: Chatani