Synthesis of 2-aryl-1,1-difluoro-1,3-enynes via consecutive cross-coupling reactions of 2,2-difluoro-1-iodoethenyl p-toluenesulfonate

Cu(I)-Catalyzed Cross-Coupling of Terminal Alkynes with Trifluoromethyl Ketone N-Tosylhydrazones: Access to 1,1-Difluoro-1,3-enynes

“…Hammond et al reported an alternative method, in which gem -difluorohomoallenyl bromides were used as the source of a 1,1-difluorovinyl moiety . More recently, Jeong et al reported studies on the synthesis of 1,1-difluoro-1,3-enynes based on Pd-catalyzed coupling reactions . However, the coupling substrates are not easy to prepare and handle.…”

Cross-Coupling Reactions of Double or Triple Electrophilic Templates for Alkene Synthesis

“…In 2014, the Jeong group reported the synthesis of 2aryl-1,1-difluoroenynes S8-2 via the Stille reaction of tosylates S8-1 (Scheme S8). 20 The alkenes S8-2 were synthesized by means of the reaction with aryltributylstannanes and dichlorobis(triphenylphosphine)palladium (10 mol%). The introduction of simple aryl groups was achieved in acceptable isolated yields, as illustrated by the examples S8-2a-c.…”

Synthesis of gem-Difluoroallylboronates via FeCl2-Catalyzed Boration/β-Fluorine Elimination of Trifluoromethyl Alkenes

“…Recently, gem -difluoroolefination of diazo compounds as an efficient approach toward gem -difluorovinyl derivatives has also been reported . Alternatively, gem -difluorovinyl derivatives have been prepared via a direct introduction of gem -difluorovinylidene unit with gem -difluorovinyl lithium, copper, zinc, tin, silicon, halogen, tosylate, or borane . Finally, nucleophilic addition of nitrogen, sulfur, and carbon nucleophiles on trifluoromethylalkenes followed by β-fluorine elimination is also an efficient approach to gem -difluorovinyl derivatives …”