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Fluorination of Aryl-Alkenyl-Iodonium Salts for Preparing Alkenyl Fluorides

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Fluorination

Part of the book series: Synthetic Organofluorine Chemistry ((SYOC))

Brief Introduction

Alkenyl fluorides are important building blocks for constructing fluoroalkene moiety containing complex organic molecules, which may possess interesting biological activities and thus are particularly attractive to the pharmaceutical and agrochemical industries [6174,6175,3]. In addition, they can be used as monomers for polymerization and copolymerization to form fluoropolymers with certain special properties [6177,6178,6]. Numerous synthetic approaches have been developed to obtain selectively functionalized alkenyl fluorides which can be classified into five major categories based upon the organic reactions: (1) Horner-Wadsworth-Emmons, Horner-Wittig, Julia, Peterson, and Reformatsky-type olefination reactions, (2) hydrofluorination of alkynes, (3) electronic fluorination of alkenyl metals, (4) reductive elimination reaction of multi-halo compounds, and (5) various metal catalyzed cross-coupling reactions using fluoroalkenyl moiety containing synthons, etc. These...

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References

  1. BESSET, T., POISSON, T. & PANNECOUCKE, X. 2015. Direct Vicinal Difunctionalization of Alkynes: An Efficient Approach Towards the Synthesis of Highly Functionalized Fluorinated Alkenes. Eur. J. Org. Chem., 2015, 2765–2789.

    CAS  Google Scholar 

  2. LANDELLE, G., BERGERON, M., TURCOTTE-SAVARD, M.-O. & PAQUIN, J.-F. 2011. Synthetic approaches to monofluoroalkenes. Chem. Soc. Rev., 40, 2867–2908.

    CAS  PubMed  Google Scholar 

  3. ZHANG, X. & CAO, S. 2017. Recent advances in the synthesis and C-F functionalization of gem-difluoroalkenes. Tetrahedron Lett., 58, 375–392.

    CAS  Google Scholar 

  4. AMEDURI, B. 2010. Controlled radical (Co)polymerization of fluoromonomers. Macromolecules (Washington, DC, U. S.), 43, 10163–10184.

    CAS  Google Scholar 

  5. AMEDURI, B. & BOUTEVIN, B. 2000. Copolymerization of fluorinated monomers: recent developments and future trends. J. Fluorine Chem., 104, 53–62.

    CAS  Google Scholar 

  6. KOSTOV, G., AMEDURI, B. & BOUTEVIN, B. 2002. New approaches to the synthesis of functionalized fluorine-containing polymers. J. Fluorine Chem., 114, 171–176.

    CAS  Google Scholar 

  7. CHAMPAGNE, P. A., DESROCHES, J., HAMEL, J.-D., VANDAMME, M. & PAQUIN, J.-F. 2015. Monofluorination of Organic Compounds: 10 Years of Innovation. Chem. Rev. (Washington, DC, U. S.), 115, 9073–9174.

    CAS  Google Scholar 

  8. HARA, S. 2012. Stereoselective synthesis of mono-fluoroalkenes. Top. Curr. Chem., 327, 59–86.

    CAS  PubMed  Google Scholar 

  9. OHASHI, M. & OGOSHI, S. 2015. Catalytic Transformations of Fluorinated Olefins. Top. Organomet. Chem., 52, 197–215.

    CAS  Google Scholar 

  10. PFUND, E., LEQUEUX, T. & GUEYRARD, D. 2015. Synthesis of Fluorinated and Trifluoromethyl-Substituted Alkenes through the Modified Julia Olefination: An Update. Synthesis, 47, 1534–1546.

    CAS  Google Scholar 

  11. YANAI, H. & TAGUCHI, T. 2011. Synthetic Methods for Fluorinated Olefins. Eur. J. Org. Chem., 2011, 5939–5954.

    CAS  Google Scholar 

  12. ZAJC, B. & KUMAR, R. 2010. Synthesis of fluoroolefins via Julia-Kocienski olefination. Synthesis, 1822–1836.

    Google Scholar 

  13. PRESHLOCK, S., TREDWELL, M. & GOUVERNEUR, V. 2016. 18F–Labeling of Arenes and Heteroarenes for Applications in Positron Emission Tomography. Chem. Rev. (Washington, DC, U. S.), 116, 719–766.

    CAS  Google Scholar 

  14. YUSUBOV, M. S., MASKAEV, A. V. & ZHDANKIN, V. V. 2011. Iodonium salts in organic synthesis. ARKIVOC (Gainesville, FL, U. S.), 370–409.

    Google Scholar 

  15. YUSUBOV, M. S., SVITICH, D. Y., LARKINA, M. S. & ZHDANKIN, V. V. 2013. Applications of iodonium salts and iodonium ylides as precursors for nucleophilic fluorination in Positron Emission Tomography. ARKIVOC (Gainesville, FL, U. S.), 364–395, 32 pp.

    Google Scholar 

  16. OCHIAI, M., OSHIMA, K. & MASAKI, Y. 1994. Synthesis of (Z)-1,2-dihalo-1-alkenes by the reaction of (Z)-(β-halovinyl)phenyliodonium salts with n-Bu4NX or KX/CuX. Competitions between nucleophilic vinylic substitutions and aromatic substitutions. Chem. Lett., 871–4.

    Google Scholar 

  17. HARA, S., YOSHIDA, M., FUKUHARA, T. & YONEDA, N. 1998. Stereo- and regioselective addition of iodotoluene difluoride to alk-1-ynes. Selective synthesis of 2-fluoro-1-iodoalk-1-enes. Chem. Commun. (Cambridge), 965–966.

    Google Scholar 

  18. HARA, S., YAMAMOTO, K., YOSHIDA, M., FUKUHARA, T. & YONEDA, N. 1999. Stereoselective synthesis of (E)-β-fluoro-α,β-unsaturated esters by carbonylation of (E)-2-fluoro-1-iodo-1-alkenyliodonium salts. Tetrahedron Lett., 40, 7815–7818.

    CAS  Google Scholar 

  19. YOSHIDA, M., HARA, S., FUKUHARA, T. & YONEDA, N. 2000. Stereo- and regioselective synthesis of (E,E)-δ-fluoro-α,β,γ,δ-unsaturated carbonyl compounds by Heck-type reaction of (fluoroalkenyl)iodonium salts. Tetrahedron Lett., 41, 3887–3890.

    CAS  Google Scholar 

  20. YOSHIDA, M., NAGAHARA, D., FUKUHARA, T., YONEDA, N. & HARA, S. 2001a. Regio- and stereoselective synthesis of fluoroalkadienes using β-fluoroalkenyliodonium salt. J. Chem. Soc., Perkin Trans. 1, 2283–2288.

    Google Scholar 

  21. YOSHIDA, M., YOSHIKAWA, S., FUKUHARA, T., YONEDA, N. & HARA, S. 2001b. Stereoselective synthesis of (E)-1-fluoro-1,3-enynes. Tetrahedron, 57, 7143–7148.

    CAS  Google Scholar 

  22. YOSHIDA, M. & HARA, S. 2003. Stereoselective Synthesis of (Z)-2-Fluoro-1-alkenyl(phenyl)iodonium Tetrafluoroborates. Org. Lett., 5, 573–574.

    CAS  PubMed  Google Scholar 

  23. YOSHIDA, M., KAWAKAMI, K. & HARA, S. 2004a. An efficient stereoselective synthesis of (E)-β-fluoroalkenyliodonium salts. Synthesis, 2821–2824.

    Google Scholar 

  24. YOSHIDA, M., KOMATA, A. & HARA, S. 2004b. Stereoselective synthesis of (Z)-β-fluoro-α,β-unsaturated esters from (Z)-2-fluoro-1-alkenyliodonium salts. J. Fluorine Chem., 125, 527–529.

    CAS  Google Scholar 

  25. YOSHIDA, M., KOMATA, A. & HARA, S. 2006. Stereoselective synthesis of fluoroalkenes via (Z)-2-fluoroalkenyliodonium salts. Tetrahedron, 62, 8636–8645.

    CAS  Google Scholar 

  26. GUAN, T., YOSHIDA, M., OTA, D., FUKUHARA, T. & HARA, S. 2005. Stereoselective synthesis of insect sex pheromone analogs having a fluorine atom on their double bonds. J. Fluorine Chem., 126, 1185–1190.

    CAS  Google Scholar 

  27. HARA, S., GUAN, T. & YOSHIDA, M. 2006. Stereoselective Generation of (E)- and (Z)-2-Fluoroalkylidene-Type Carbenoids from (2-Fluoro-1-alkenyl)iodonium Salts and Their Application for Stereoselective Synthesis of Fluoroalkenes. Org. Lett., 8, 2639–2641.

    CAS  PubMed  Google Scholar 

  28. GUAN, T., YOSHIDA, M. & HARA, S. 2007. Stereoselective Synthesis of (E)- and (Z)-Fluoroalkenylboronates Using 2-Fluoroalkylideneiodonium Ylides Generated from (2-Fluoro-1-alkenyl)iodonium Salts. J. Org. Chem., 72, 9617–9621.

    CAS  PubMed  Google Scholar 

  29. SAKAI, M., GUAN, T. & HARA, S. 2007. Stereoselective synthesis of 4-fluoro-1,3-alkadienylboronates and their application in the stereoselective synthesis of fluoropolyenes. J. Fluorine Chem., 128, 1444–1448.

    CAS  Google Scholar 

  30. GUAN, T., TAKEMURA, K., SENBOKU, H., YOSHIDA, M. & HARA, S. 2008. An efficient synthesis of fluorocyclopentenes using fluoroalkylidenecarbenes. Tetrahedron Lett., 49, 76–79.

    CAS  Google Scholar 

  31. NGUYEN, T.-H., ABARBRI, M., GUILLOTEAU, D., MAVEL, S. & EMOND, P. 2011. Nucleophilic fluorination of alkynyliodonium salts by alkali metal fluorides: access to fluorovinylic compounds. Tetrahedron, 67, 3434–3439.

    CAS  Google Scholar 

  32. SHIMOBABA, S., TAHARA, R. & HARA, S. 2012. E- or Z-selective synthesis of trisubstituted (2-fluoroalkenyl)iodonium salts by the reaction of (2-fluoroalkenyl)iodonium ylides with aldehydes. J. Fluorine Chem., 142, 105–108.

    CAS  Google Scholar 

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Correspondence to Wenchao Qu .

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Qu, W., Li, X. (2020). Fluorination of Aryl-Alkenyl-Iodonium Salts for Preparing Alkenyl Fluorides. In: Hu, J., Umemoto, T. (eds) Fluorination. Synthetic Organofluorine Chemistry. Springer, Singapore. https://doi.org/10.1007/978-981-10-3896-9_13

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