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, CO2 Et, CONEt2 and NMeCO2t Bu. 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.