Chloropentafluorobenzene

Preparation of Trifluorostyrenes via Palladium-Catalyzed Coupling of Arylboronic Acids with Chloro- and Bromotrifluoroethylene

“…α,β,β-Trifluorostyrene (TFS) and its derivatives are interesting monomers for fluorinated polymers, , mainly due to their unique structure that combines a trifluorovinyl group and a benzene ring. The polymers contain a perfluorinated main chain and often exhibit high thermal and chemical stability and, more importantly, high solubility that allows the polymers to be more processable.…”

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

“…Based on this method, we have recently developed an excellent room temperature preparation of the trifluorovinylzinc reagent by the metallation of HFC-134a, and this reagent was utilized for Pd(0) catalyzed coupling reactions with aryl iodides to obtain a,b,b-trifluorostyrenes under mild reaction conditions [26,27]. We have then applied similar strategy for the synthesis of a-halo-b,b-difluorovinylzinc reagents [CF 2 CXZnX, where X = Cl, Br, I] and the corresponding a-halo-b,b-difluorostyreness by the metallation of the corresponding commercially available precursors [23,28,29]. This methodology serves as the first general methodology for the synthesis of a-halo-b,bdifluorovinylzinc reagents and corresponding a-halo-b,bdifluorostyrenes.…”

Fluorinated Organozinc Reagents

“…The precursors (CF 3 CH 2 X) are commercially available, cheap or moderately priced, and in some cases (X = F) is a cost-effective entry to commercially useful compounds. The α-bromo-and α-iodostyrenes also provide useful precursors to 1,1-difluoromethylene olefins via subsequent Suzuki couplings 27 The third method for the preparation of fluorinated vinylzinc reagent does not involve the use of the unstable fluorinated vinyllithium reagents, but employs the direct reaction of fluorovinyl bromides or iodides with activated zinc 28 . This route avoids the lowtemperature problems associated with the limited thermal stability of fluorovinyllithium reagents and utilizes direct insertion of Zn • into the carbon-halogen bond (equation 42).…”