1979-53-9Relevant academic research and scientific papers
Metal Dehalogenation Route To Reactive Fluoroolefins
Burton, D. J.,Kesling, H. S.,Naae, D. G.
, p. 293 - 298 (1981)
Metal dehalogenation of bromodifluoromethyltriphenylphosphonium bromide with Cd, Zn, or Hg provides a practical route to fluoroolefins that contain an allylic halogen or a pentafluorophenyl group.No SN2' or ring substituted products are observed.
An I(I)/I(III) Catalysis Route to the Heptafluoroisopropyl Group: A Privileged Module in Contemporary Agrochemistry
Martín-Heras, Víctor,Daniliuc, Constantin G.,Gilmour, Ryan
, p. 4203 - 4212 (2021/06/02)
The heptafluoroisopropyl group is emerging as a privileged chemotype in contemporary agrochemistry and features prominently in the current portfolio of leading insecticides. To reconcile the expansive potential of this module with the synthetic challenges
Deoxygenative gem-difluoroolefination of carbonyl compounds with (chlorodifluoromethyl)trimethylsilane and triphenylphosphine
Wang, Fei,Li, Lingchun,Ni, Chuanfa,Hu, Jinbo
supporting information, p. 344 - 351 (2014/03/21)
Background: 1,1-Difluoroalkenes cannot only be used as valuable precursors for organic synthesis, but also act as bioisosteres for enzyme inhibitors. Among various methods for their preparation, the carbonyl olefination with difluoromethylene phosphonium ylide represents one of the most straightforward methods. Results: The combination of (chlorodifluoromethyl)trimethylsilane (TMSCF2Cl) and triphenylphosphine (PPh3) can be used for the synthesis of gem-difluoroolefins from carbonyl compounds. Comparative experiments demonstrate that TMSCF2Cl is superior to (bromodifluoromethyl)trimethylsilane (TMSCF2Br) and (trifluoromethyl)trimethylsilane (TMSCF3) in this reaction. Conclusion: Similar to many other Wittig-type gem-difluoroolefination reactions in the presence of PPh3, the reaction of TMSCF2Cl with aldehydes and activated ketones is effective.
Preparation of β,β-Difluoro-α-(trifluoromethyl)styrenes by Palladium-Catalyzed Coupling of Aryl Iodides with Pentafluoropropen-2-ylzinc Reagent
Morken, Peter A.,Burton, Donald J.
, p. 1167 - 1172 (2007/10/02)
Substituted aromatic iodides are functionalized by pentafluoropropen-2-ylzinc, CF3C(ZnX)=CF2 (X = Br, I, or CF2=CCF3-), in the presence of Pd(PPh3)4 to give the corresponding arenes in good yields.This is particularly attractive for the preparation of title styrenes substituted with groups such as -NO2 or CO2R, which are incompatible with organomagnesium reagents.The best yields of the title styrenes with electron-donating substituents were obtained in DMF.For electron-withdrawing substituents, the best results were achieved in triglyme.A correlation was observed between Hammett ? constants and 19F NMR chemical shifts (R = 0.93-0.99, n = 8) and 2JF-F coupling constants (R = 0.94, n = 8).
