Reactions of trifluorovinyllithium and 1-chloro-2,2-difluorovinyllithium: the synthesis of fluorinated heterocycles

(Fluoroorgano)fluoroboranes and -borates. 12. Reactions of (Trifluorovinyl)lithium with Chloro-, Chloromethoxy-, and (Trifluorovinyl)methoxyboranes, a Useful Route to (Trifluorovinyl)fluoroborate Salts

“…Synthesis of LiCF  CF 2 . (A modified procedure based on the initial and latest protocols was used.) A 250 mL three-necked round-bottomed flask supplied with a magnetic stirrer bar and a low-temperature thermometer was charged with 50 mL of dry ether under an atmosphere of dry argon and cooled to −78 °C before CF 3 CH 2 F (3 g, 29 mmol) was condensed into the solution.…”

Repurposing of F-gases: challenges and opportunities in fluorine chemistry

“…The trifluorovinyllithium moiety formed at À78 1C can react with a wide range of electrophiles including metal halides, main group halides, CO 2 , aldehydes and epoxides. [190][191][192][193][194][195][196][197][198][199][200][201][202][203][204][205][206][207][208] Using this method with transition metal halides resulted in the formation of transition metal complexes with a trifluorovinyl ligand. 191,193 Other reports include the transfer of the trifluorovinyl group onto zinc chlorides for application in palladium-catalysed Negishi cross-coupling reactions (Scheme 4b).…”

Polyfluorinated Ethanes as Versatile Fluorinated C2-Building Blocks for Organic Synthesis

“…The reaction of this organolithiums with 2-trifluoromethyl aniline leads to the formation of quinoneimine intermediate 256 by dehydrofluorination. Subsequent addition of fluorinated vinyl lithiums gave 2,3,4-trifluoroquinoline and 3-chloro-2,4-difluoroquinoline 257 in good yields (Scheme ) …”

“…Subsequent addition of fluorinated vinyl lithiums gave 2,3,4trifluoroquinoline and 3-chloro-2,4-difluoroquinoline 257 in good yields (Scheme 137). 313 Application of CF 3 CH 2 I has expanded the synthetic scope of the method on the synthesis of 2,2-difluoro-1-iodovinyl derivatives. Difluoroiodovinyl lithium CF 2 CILi was generated by the treatment of CF 3 CH 2 I with LDA in THF at low temperature.…”