Litcius/Paper detail

Copper-Catalyzed Defluorinative Boroarylation of Alkenes with Polyfluoroarenes

Yue Zhao, Bin Fu, Simin Wang, Yanfei Li, Xiuping Yuan, Jianjun Yin, Tao Xiong, Qian Zhang

2023Organic Letters20 citationsDOI

Abstract

A catalytic defluorinative boroarylation of alkenes with polyfluoroarenes and B 2 pin 2 with the assistance of a PCy 3 -ligated copper catalyst was developed. Taking advantage of bench-stable alkenes as latent nucleophiles and avoiding traditional reliance on stoichiometric quantities of organometallics, this method showcased good functional group compatibility and proceeded under very mild reaction conditions. A series of valuable boronate-containing polyfluoroarenes including all-carbon quaternary carboncenter-containing triaryl alkylboronates that are otherwise difficult to access were efficiently prepared.

Topics & Concepts

ChemistryNucleophileCatalysisCopperStoichiometryCompatibility (geochemistry)Organic chemistryCombinatorial chemistryChemical engineeringEngineeringFluorine in Organic ChemistryOrganoboron and organosilicon chemistryCatalytic C–H Functionalization Methods