Programmable synthesis of difluorinated hydrocarbons from alkenes through a photocatalytic linchpin strategy

Abstract

We have devised a general and versatile approach for the synthesis of diverse difluorinated alkanes and alkenes by utilizing readily accessible ClCF2SO2Na as a practical difluoromethylene linchpin.

Hydrosulfonylation of Unactivated Alkenes and Alkynes by Halogen-Atom Transfer (XAT) Cleavage of SVI–F Bond

“…In theory, any active radical species capable of forming a more thermodynamically stable bond with fluoride than this number could potentially undergo fluoride abstraction through XAT. In recent years, the photochemical oxidation of Lewis base-BH 3 complexes has emerged as a promising technology for generating the corresponding boryl radicals that could be used for XAT activation of inert halide compounds . In light of the strong BDE of the B–F bond, which has also been a robust driving force in BF 3 -mediated electrophilic activation of sulfonyl fluorides, we hypothesized that radical abstraction of fluoride by a boryl radical might also be advantageous.…”