The Preparation and Some Reactions of Trifluorovinyllithium¹

Room temperature preparation of α-chloro-β,β-difluoroethenylzinc reagent (CF2CClZnCl) by the metallation of HCFC-133a (CF3CH2Cl) and a high yield one-pot synthesis of α-chloro-β,β-difluorostyrenes

“…Normant and co-workers generated various fluorovinylzinc reagents including a-chloro-b-fluorovinylzinc reagent by the metallation of halo or hydro fluoroalkenes via the corresponding vinyllithium species [12][13][14][15][16]. But fluorinated vinyllithiums are thermally unstable and need to be generated at very low temperature in order to have reasonable yield of the zinc reagent [17][18][19].…”

Fluoroalkenyl, fluoroalkynyl and fluoroalkyl phosphines

“…Initially these compounds were prepared by the low temperature reaction of an appropriate chlorophosphine with the Grignard reagent derived from F 2 C5 5CFI [22], or LiCF5 5CF 2 derived from CF 2 5 5CFBr and MeLi [23]; these two methods accounted for the synthesis of perfluorovinyl-containing phosphines of the type P(CF5 5CF 2 ) 3 , PR 3Àn (CF5 5CF 2 ) n (n = 1,2; R = Ph, NMe 2 , NEt 2 , EtO and BuO). More recent approaches have utilised CF 3 CH 2 F (HFC-134a) as the perfluorovinyl-synthon, as shown in Scheme 1 [24], and have provided perfluorovinyl-containing phosphines with R = Cl, Et, iPr, Ph, Cy and the P-chiral compound PPhBu(CF5 5CF 2 ) [25][26][27].…”

Organometallic Compounds

“…Trifluorovinylmagnesium bromide and the lithium derivative may be obtained [39][40][41] from bromotrifluoroethene but preparation from HFC 134a, which involves metallation of trifluoroethene generated in situ, is now the more accessible route (see Section IA). Trifluorovinylmagnesium bromide and the lithium derivative may be obtained [39][40][41] from bromotrifluoroethene but preparation from HFC 134a, which involves metallation of trifluoroethene generated in situ, is now the more accessible route (see Section IA).…”