A novel direct synthesis of (2,2-difluorovinyl)benzenes from aromatic aldehydes

Reaction of CBrF2–CBrF2 with hydrazones of aromatic aldehydes

“…Recently, we reported a novel catalytic olefination reaction (COR) of aldehydes and ketones [3][4][5][6][7][8][9][10]. It was found that N-unsubstituted hydrazones of carbonyl compounds could be smoothly transformed into the various substituted alkenes by treatment with polyhalogenalkanes in the presence of catalytic amounts of CuCl.…”

“…Mass spectra were recorded on a Finnigan SSQ7000 mass spectrometer. Known azines (4a-c) were characterized by comparison of their spectral and physical data with literature [3][4][5][6][7][8][9][10]. Column chromatography was performed on silica gel (63-200 mesh, Merck).…”

Progress in Preparation ofβ,β-Difluorovinyl Compounds

“…β,β-二氟乙烯类化合物自 Franzen [3] 1962 年首次用二氟二溴甲烷、 三苯基膦和丁基锂合成以 来, 由于 β,β-二氟乙烯类化合物具有独特的物理、化学 和生物性能 [4] , 使其在多种有机氟化物中发挥重要作 用 [5] , 人们开始致力于这类化合物的合成方法研究 [6,7] .…”

The catalytic olefination reaction of aldehydes and ketones with CBr3CF3

“…Recently, we reported a novel catalytic olefination reaction (COR) of aldehydes and ketones [12][13][14][15][16][17][18][19][20]. It was found that N-unsubstituted hydrazones of carbonyl compounds could be smoothly transformed into the various substituted alkenes by treatment with polyhalogenalkanes in the presence of catalytic amounts of CuCl.…”

“…Based on COR we elaborated a novel approach to synthesis of dichloroalkenes [12], dibromoalkenes [13] vinylbromides [14] and vinyliodides [15] from aromatic and heteroaromatic carbonyl precursors as well as aliphatic compounds [16]. We found also COR applicable for the preparation of fluorocontaining alkenes using such chlorofluorocarbons as CCl 3 F [17], CCl 3 CF 3 , CCl 2 FCClF 2 [18] and also CBr 2 F 2 [19] and CF2BrCF2Br [20] as C 1 -and C 2 -building blocks.…”