3-Bromo-3,3-difluoropropene, when mixed with lithium bromide, provides a convenient route to prepare gem-(difluoroallyl) lithium, a reagent of general use in the formation of gem-difluorinated organic compounds. Umpolung asymmetric difluoroallylation of hydrazones with 3-bromo-3,3-difluoropropene (BDFP) under palladium catalysis. In addition, aldehydes and ketones reacted with 3-bromo-3,3-difluoropropene in the presence of the acid-washed zinc powder at 0°C to room temperature to afford gem-difluorohomoallyl alcohols in moderate yields[1-3].
[1] Shuai Huang. “Regio- and enantioselective umpolung gem-difluoroallylation of hydrazones via palladium catalysis enabled by N-heterocyclic carbene ligand.” Nature Communications 12 1 (2021): 6551.
[2] J.D. Langridge, S.A. Cooke, B.E. Long. “The microwave spectra, bromine nuclear electric quadrupole coupling tensor, and structure of 3-bromo-3,3-difluoropropene.” Journal of Molecular Structure 1000 1 (2011): Pages 24-28.
[3] M. Kirihara. “Indium-Mediated Reaction of 3-Bromo-3,3-difluoropropene and Bromodifluoromethylacetylene Derivatives with Aldehydes.” ChemInform 3 1 (2001).
