Revisiting Polyfluoroarenes as Radical Acceptors: Radical C–F Bond Borylation of Polyfluoroarenes with N-Heterocyclic Carbene Boranes and Synthesis of Borane-Containing Liquid Crystals
Kosuke Takahashi, Masaki Shimoi, Takashi Watanabe, Katsuhiro Maeda, Steven J. Geib, Dennis P. Curran, Tsuyoshi Taniguchi
Abstract
Polyfluoroarenes work as good radical acceptors in the thermal radical reaction with N-heterocyclic carbene boranes (NHC-boranes) in the presence of di-tert-butyl peroxide. In this reaction, a C–F bond of polyfluoroarenes is substituted with an NHC-boryl group to provide B-aryl NHC-borane derivatives. The developed synthetic method was applied to the synthesis of novel borane-containing liquid crystalline molecules having highly thermal stability.
Topics & Concepts
BoranesChemistryCarbeneBoraneBorylationArylPhotochemistryMedicinal chemistryOrganic chemistryBoronCatalysisAlkylFluorine in Organic ChemistryRadical Photochemical ReactionsOrganoboron and organosilicon chemistry