The Sulfinatodehalogenation Reaction

Abstract

Sulfinatodehalogenation is a simple and efficient reaction for the synthesis of polyfluoroalkane‐sulfinates and sulfonates. The reaction can also be applied for the polyfluoroalkylation of organic compounds. A brief account is given of its development and scope, reaction mechanism, and applications in organic synthesis.

Strategies for nucleophilic, electrophilic, and radical trifluoromethylations

“…The reaction is promoted by sodium dithionite and related reagent systems [126][127][128]. Application to this reaction in sugar chemistry was reported by Portella and co-workers [129,130].…”

Synthesis of α,α-difluoro-γ-butyrolactones via ethyl iododifluoroacetate

“…Previous reports by Huang et al [12][13][14] documented that the addition of perfluoroalkyl iodides to alkenes can be initiated by sodium dithionite. A free radical chain involving a single electron transfer mechanism has been proposed in the addition reaction [15].…”

Sodium dithionite initiated addition of 1-bromo-1-chloro-2,2,2-trifluoroethane to β-pinene

“…The reaction of perfluoroalkyl halides (R F I, R F Br) with sodium dithionite in aqueous medium, known as ''sulfinatodehalogenation'', provides an easy way of generating perfluoroalkyl radicals [1,2]. These electron-deficient radicals could be effectively trapped by electron-rich substrates like alkenes, alkynes and arenes to give addition or substitution products.…”