Stereoselective Synthesis of (Z)-Perfluoroalkyl-1-iodo-1-triisopropyl Silylalkenes: A Convenient Route to Perfluoroalkyl-Substituted Unsaturated Synthons

REFERENCES

• (a) Johns , K. ; Stead , G. Fluoroproducts: The extremophiles . J. Fluorine Chem. 2000 , 104 , 5 – 18 ; (b) Kirsch , P. Modern Fluoroorganic Chemistry: Synthesis, Reactivity, Applications. Wiley-VCH Verlag: Weinheim, 2004.
   Web of Science ®Google Scholar
• Furin , G. G. Some new aspects in the application of perfluoroalkyl halides in the synthesis of fluorine-containing organic compounds . Russ. Chem. Rev. 2000 , 69 , 491 – 522 .
   Google Scholar
• Estelrich , A. R. ; Améduri , B. ; López Calahorra , F. Radical polymerization of 1H,1H,2H,2H-perfluoro-3,5-alkyldiynol and 1H,1H-perfluoro-2,4-alkyldiynol acrylates and methacrylates: A new family of fluorinated polymers . Macromol. Chem. Phys. 2004 , 205 , 223 – 229 .
   Web of Science ®Google Scholar
• Huang , W.-Y. ; Lü , L. ; Zhang , Y-F. Studies on sulfinatodehalogenation, XVI: Sodium dithionite-initiated addition of perfluoroalkyl iodides to terminal alkynes . Chin. J. Chem. 1990 , 350 – 354 .
   Google Scholar
• Wang , Z. ; Lu , X. Stereoselective synthesis of perfluoroalkylated (E,E)-dienes from perfluoroalkylated alkynes: The synthesis of fluorinated analogs of Lepidoptera pheromones . Tetrahedron 1995 , 51 , 11765 – 11774 .
   Google Scholar
• Brace , N. O. ; Van Elswik , J. E. Evidence for free-radical reductive dehalogenation in reaction of zinc and acid with 1-perfluoroalkyl-2-iodoalkanes and with 1-perfluoroalkyl-2-iodoalkenes . J. Org. Chem. 1976 , 41 , 766 – 771 .
   Web of Science ®Google Scholar
• Ishihara , T. ; Kuroboshi , M. ; Okada , Y. New efficient palladium-catalyzed perfluoroalkylation of carbon–carbon multiple bonds with F-alkyl iodides: An expedient route to F-alkylated alkyl and alkenyl iodides . Chem. Lett. 1986 , 11 , 1895 – 1896 .
   Google Scholar
• (a) Haszeldine , R. N. Reactions of fluorocarbon radicals, V: Alternative syntheses for (trifluoromethyl)acetylene (3,3,3-trifluoropropyne) and the influence of polyfluoro groups on adjacent hydrogen and halogen atoms . J. Chem. Soc. 1951 , 2495 – 2504 ; (b) Haszeldine , R. N. ; Steele , B. R. The addition of free radicals to unsaturated systems, II: Radical addition of olefins of the type RCH:CH2 . J. Chem. Soc. 1953 , 1199 – 1206 .
   Google Scholar
• (a) Brace , N. O. Some approaches to the synthesis of fluorinated alcohols and esters, II: Use of fluoroalkyl iodides for the synthesis of fluoroalkyl alkanols . J. Fluorine Chem. 1982 , 20 , 313 – 327 ; (b) Baum , K. ; Bedford , C. D. ; Hunadi , R. J. Synthesis of fluorinated acetylenes . J. Org. Chem. 1982 , 47 , 2251 – 2257 .
   Google Scholar
• Haszeldine , R. N. ; Leedham , K. Reactions of fluorocarbon radicals, VI: Hydration of trifluoromethyl- and pentafluoroethyl-substituted acetylenes . J. Chem. Soc. 1952 , 3483 – 3490 ; (b) Leedham , K. ; Haszeldine , R. N. Addition of free radicals to unsaturated systems, VIII: The direction of radical-addition to alkyl- and perfluoroalkyl-acetylenes . J. Chem. Soc. 1954 , 1634 – 1638 .
   Google Scholar
• (a) Benefice-Malouet , S. ; Blancou , H. ; Calas , P. ; Commeyras , A. Synthesis of 2-(perfluorohexyl)ethanol by electrochemical reduction of 1-iodo-2-(perfluorohexyl)ethane on carbon fibers . J. Fluorine Chem. 1988 , 39 , 245 – 260 ; (b) Calas , P. ; Moreau , P. ; Commeyras , A. An efficient electrochemical route to (perfluoroalkyl)alkynes . J. Chem. Soc. Chem. Commun. 1982 , 433 – 434 .
   Google Scholar
• (a) Blancou , H. ; Commeyras , A. Addition of perfluoroalkyl iodides (RFI) to 2-methyl-3-butyn-2-ol activated by suspended zinc dust in different solvents . J. Fluorine Chem. 1994 , 68 , 21 – 24 ; (b) Jennings , M. P. ; Cork , E. A. ; Ramachandran , P. V. A facile synthesis of perfluoroalkyl vinyl iodides and their palladium-mediated cross-coupling reactions . J. Org. Chem. 2000 , 65 , 8763 – 8766 .
   Google Scholar