Living Edition
| Editors: Jinbo Hu, Teruo Umemoto

Fluorination of Allenes

  • Xue Zhang
  • Shengming MaEmail author
Living reference work entry
DOI: https://doi.org/10.1007/978-981-10-1855-8_46-1


Owing to the presence of two C=C bonds in allenes, the reactivities of allenes are very different from those of alkenes and alkynes. The unique structure of allenes allows a great number of useful transformations [1, 2, 3, 4]. During the past several decades, tremendous progress has been made in fluorination of alkenes and alkynes with different fluorination reagents [5, 6, 7]. Alkene fluorination is an efficient way to alkyl fluorides, whereas the same reaction of alkynes provides the alkenyl fluorides [5]. Fluorination of allenes provides another potential pathway to afford the alkenyl, 1,3-alkadienyl, allylic, propargylic, and alkynylic fluorides. However, due to the lack of efficient control of the regio- or stereoselectivity, the fluorination of allene compounds has not yet received extensive investigation. So far only limited examples of fluorination of allenes have been reported. From the mechanistic aspect, most of these reactions can be classified into three...

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  1. 1.
    Ma S (2005) Chem Rev 105:2829CrossRefPubMedGoogle Scholar
  2. 2.
    Ma S (2003) Acc Chem Res 36:701CrossRefPubMedGoogle Scholar
  3. 3.
    Sydnes LK (2003) Chem Rev 103:1133CrossRefPubMedGoogle Scholar
  4. 4.
    Zimmer R, Dinesh CU, Nandanan E, Khan FA (2000) Chem Rev 100:3067CrossRefPubMedGoogle Scholar
  5. 5.
    Champagne PA, Desroches J, Hamel JD, Vandamme M, Paquin JF (2015) Chem Rev 115:9073CrossRefPubMedGoogle Scholar
  6. 6.
    Brown JM, Gouvernuer V (2009) Angew Chem Int Ed 48:8610CrossRefGoogle Scholar
  7. 7.
    Grushin VV (2010) Acc Chem Res 43:160CrossRefPubMedGoogle Scholar
  8. 8.
    Banks RE, Lawrence NJ, Popplewell AL (1994) Synlett 1994:831CrossRefGoogle Scholar
  9. 9.
    Nyffeler PT, Duron SG, Burkart MD, Vincent SP, Wong CH (2005) Angew Chem Int Ed 44:192CrossRefGoogle Scholar
  10. 10.
    Singh RP, Shreeve JM (2004) Acc Chem Res 37:31CrossRefPubMedGoogle Scholar
  11. 11.
    Pacheco MC, Gouverneur V (2005) Org Lett 7:1267CrossRefPubMedGoogle Scholar
  12. 12.
    Carroll L, Pacheco MC, Garcia L, Gouverneur V (2006) Chem Commun 2006: 4113CrossRefGoogle Scholar
  13. 13.
    Carroll L, McCullough S, Rees T, Claridge TDW, Gouverneur V (2008) Org Biomol Chem 6: 1731CrossRefPubMedGoogle Scholar
  14. 14.
    Yang H, Xu B, Hammond GB (2008) Org Lett 10:5589CrossRefPubMedGoogle Scholar
  15. 15.
    Zhou C, Li J, Lü B, Fu C, Ma S (2008) Org Lett 10:581CrossRefPubMedGoogle Scholar
  16. 16.
    He G, Fu C, Ma S (2009) Tetrahedron 65:8035CrossRefGoogle Scholar
  17. 17.
    Zhou C, Ma Z, Gu Z, Fu C, Ma S (2008) J Org Chem 73:772CrossRefPubMedGoogle Scholar
  18. 18.
    Lü B, Fu C, Ma S (2010) Org Biomol Chem 8:274CrossRefPubMedGoogle Scholar
  19. 19.
    Cui H, Chai Z, Zhao G, Zhu S (2009) Chin J Chem 27:189CrossRefGoogle Scholar
  20. 20.
    Banks RE, Braithwaite A, Haszeldine RN, Taylor DR (1969) J Org Chem C 1969:454CrossRefGoogle Scholar
  21. 21.
    He Y, Shen N, Fan X, Zhang X (2013) Tetrahedron 69:8818CrossRefGoogle Scholar
  22. 22.
    Xue C, Jiang X, Fu C, Ma S (2013) Chem Commun 49:5651CrossRefGoogle Scholar
  23. 23.
    Zhao Z, Racicot L, Murphy GK (2017) Angew Chem Int Ed 56:11620CrossRefGoogle Scholar
  24. 24.
    Luo HQ, Hu XH, Loh TP (2010) Tetrahedron Lett 51:1041CrossRefGoogle Scholar
  25. 25.
    Xu T, Mu X, Peng H, Liu G (2011) Angew Chem Int Ed 50:8176CrossRefGoogle Scholar
  26. 26.
    Liu Y, Zhu J, Qian J, Xu Z (2012) J Org Chem 77:5411CrossRefPubMedGoogle Scholar
  27. 27.
    Braun MG, Katcher MH, Doyle AG (2013) Chem Sci 4:1216CrossRefGoogle Scholar
  28. 28.
    Liu S, Zhao J, Zhang G (2015) Tetrahedron Lett 56:2214CrossRefGoogle Scholar

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© Springer Nature Singapore Pte Ltd. 2018

Authors and Affiliations

  1. 1.State Key Laboratory of Organometallic ChemistryShanghai Institute of Organic Chemistry, Chinese Academy of SciencesShanghaiChina
  2. 2.Center for Molecular Recognition and Synthesis, Department of ChemistryFudan UniversityShanghaiChina