Synthesis of difluoromethylated benzylborons via rhodium(I)-catalyzed fluorine-retainable hydroboration of gem-difluoroalkenes

The synthesis of borylated organofluorines is of great interest due to their potential values as synthons in modular construction of fluorine-containing molecules. Reported herein is a rhodium-catalyzed hydroboration of aryl gem-difluoroalkenes leading to a series of alpha-difluoromethylated benzylborons. The use of cationic rhodium catalyst and a biphosphine ligand with large bite angle was crucial for reactivity by offering good regioselectivity and diminishing the undesired beta-F elimination. Preliminary derivatizations of the products were conducted to showcase the utility of this protocol. (C) 2020 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.

Automated summary

The study focuses on the synthesis of borylated organofluorines through a rhodium-catalyzed hydroboration reaction, leading to a series of alpha-difluoromethylated benzylborons. The use of a specific type of rhodium catalyst and biphosphine ligand plays a crucial role in the synthesis of the products.