title: Catalytic Double Carbon-Boron Bond Formation for the Synthesis of Cyclic Diarylborinic Acids as Versatile Building Blocks for π-Extended Heteroarenes.
abstract: The first catalytic synthesis of cyclic diarylborinic acids is developed using a dihydroaminoborane reagent as the boron source. Unlike previously reported methods that use organolithium reagents, this method allows the easy synthesis of cyclic diarylborinic acids bearing a range of functionalities including CN, CO2Et, CONEt2and NMeCO2tBu. Furthermore, these cyclic diarylborinic acids provide rapid access to skeletal diversity, in particular they enable the synthesis of six- to nine-membered π-extended heteroarenes through simple cross-coupling reactions, which are important synthetic targets in both advanced materials and pharmaceuticals.
authors.affiliation: Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka, 565-0871, Japan.
authors.forename: Takuya
authors.initials: T
authors.lastname: Igarashi
authors.affiliation: Center for Atomic and Molecular Technologies, Graduate School of Engineering, Osaka University, Suita, Osaka, 565-0871, Japan.
authors.forename: Mamoru
authors.initials: M
authors.lastname: Tobisu
authors.affiliation: Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka, 565-0871, Japan.
authors.forename: Naoto
authors.initials: N
authors.lastname: Chatani
keywords: aminoborane; borylation; diarylborinic acid; heteroarene; palladium