Living Edition
| Editors: Jinbo Hu, Teruo Umemoto

Et3N·3HF Complex Fluorination for Preparing Alkyl Fluorides

  • Günter HaufeEmail author
Living reference work entry
DOI: https://doi.org/10.1007/978-981-10-1855-8_26-1


Fluorinated organic compounds, both analogues of natural products and synthetic materials, gain enormous interest by organic and medicinal chemists, biochemists, material scientists, and others because of its unique chemical properties and biological activity. Consequently, there is a continuously growing demand of methods to synthesize such compounds. Although plenty of methods to introduce fluorine and fluorinated groups into organic compounds do exist, not all used reagents can be handled easily and safely in ordinary organic chemistry laboratories. A frequently used fluorination reagent is the triethylamine trihydrofluoride complex, Et3N·3HF [triethylamine tris(hydrogenfluoride)] as a source of nucleophilic fluoride [1, 2, 3, 4].

Originally, Et3N·3HF was formed in situ for ring opening of epoxides [5]. In 1980, Franz prepared the neat reagent by addition of an ethereal solution of anhydrous HF to a slight excess of Et3N at 0 °C, followed by distillation of the...

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  1. 1.
    Yoneda N (1991) The combination of hydrogen fluoride with organic bases as fluorination agents. Tetrahedron 47:5329–5365.CrossRefGoogle Scholar
  2. 2.
    McClinton MA (1995) Triethylamine tris(hydrogen fluoride): applications in synthesis. Aldrichim Acta 28:31–35.Google Scholar
  3. 3.
    Haufe G (1996) Triethylamine trishydrofluoride in synthesis. J Prakt Chem 338:99–113.CrossRefGoogle Scholar
  4. 4.
    Dai X, Wang Y, Zhao S (2009) Advances in the application of triethylamine tris(hydrofluoride) to organic synthesis. Chin J Org Chem 29:1307–1316.Google Scholar
  5. 5.
    Aranda G, Jullien J, Martin JA (1966) Synthèse et structure de fluoroalcools arylcyclaniques et arylaliphatiques. Bull Soc Chim Fr 2850–2857, and references cited therein.Google Scholar
  6. 6.
    Franz R (1980) Über Trishydrofluoride tertiärer Amine und ihren Einsatz als Fluorierungsmittel. J Fluorine Chem 15:423–434.CrossRefGoogle Scholar
  7. 7.
    Wiechert D, Mootz D, Franz R, Siegemund G (1998) Amine-poly(hydrogen fluoride) solid complexes: new studies of formation, crystal structures, and Hn-1Fn ion diversity. Chem Eur J 4:1043–1047.CrossRefGoogle Scholar
  8. 8.
    Giudicelli MB, Picq D, Veyron B (1990) Et3N·2HF, a new convenient reagent for nucleophilic fluorine displacement reactions. Tetrahedron Lett 31:6527–6530.CrossRefGoogle Scholar
  9. 9.
    Zhu W, Li Z, Yao L, Zheng Z, Zou X (2012) One-pot α-nucleophilic fluorination of acetophenones by DBDMH and Et3N∙3HF. Chin J Org Chem 32:1146–1149.CrossRefGoogle Scholar
  10. 10.
    Sait-Jalmes L (2006) Selective aliphatic fluorination by halogen exchange in mild conditions. J Fluorine Chem 127:85–90.CrossRefGoogle Scholar
  11. 11.
    Jouen C, Pommelet JC (1997) Monofluorination of α-dichlorosulfides: a short access to α-fluoro polyfunctionalised thioethers. Tetrahedron 53:12565–12574.CrossRefGoogle Scholar
  12. 12.
    Saluzzo C, Alvernhe G, Haufe G (1990) Synthesis of β-fluoroalkyl phenyl thioethers (or methyl) thioethers by sulfur-assisted halogen exchange with trimethylamine tris-hydrofluoride. J Fluorine Chem 47:467–479.CrossRefGoogle Scholar
  13. 13.
    Muffler H, Siegemund G, Schwertfeger W (1982) Cyclisierung unter Beteiligung von Fluoridionen: 4,5-Perfluor-1,3-dioxolane. J Fluorine Chem 21:107–132.Google Scholar
  14. 14.
    Muffler H, Franz R (1979) Verfahren zur Herstellung organischer Fluorverbindungen. Ger Pat DE 2.823.969 A1.Google Scholar
  15. 15.
    Kudzma LV, Huang CG, Lessor RA, Rozov LA, Afrin S, Kallashi F, McCutcheon C, Ramig K (2001) Diisopropylethylamine mono(hydrogen fluoride) for nucleophilic fluorination of sensitive substrates: synthesis of sevoflurane. J Fluorine Chem 111:11–16.CrossRefGoogle Scholar
  16. 16.
    Dolbier Jr WR, Wang F, Tang X, Thomoson CS, Wang L (2014) Three step procedure for the preparation of aromatic and aliphatic difluoromethyl ethers from phenols and alcohols using a chlorine/fluorine exchange methodology. J Fluorine Chem 160:72–76.CrossRefGoogle Scholar
  17. 17.
    Nebois P, Picq D, Anker D (1990) Synthesis of 3-deoxy-3-fluoroglucosamine derivatives. J Carboh Chem 9:359–368.CrossRefGoogle Scholar
  18. 18.
    López JC, Bernal-Albert P, Uriel C, Gómez AM (2008) Ready transformation of partially unprotected thioglycosides in glycosyl fluorides mediated by NIS/HF-pyridine or Et3N·3HF. Eur J Org Chem 2008:5037–5041.CrossRefGoogle Scholar
  19. 19.
    Hunter L, Kirsch P, Slawin AMZ, O’Hagan D (2009) Synthesis and Structure of stereoisomeric multivicinal hexafluoroalkanes. Angew Chem Int Ed 48:5457–5460.CrossRefGoogle Scholar
  20. 20.
    Durie AJ, Slawin AMZ, Lebl T, Kirsch P, O’Hagan D (2011) Synthesis and structure of all-syn-1,2,3,4-tetrafluorocyclohexane. Chem Commun 47:8265–8267.CrossRefGoogle Scholar
  21. 21.
    Durie AJ, Fujiwara T, Al-Maharik N, Slawin AMZ, O’Hagan D (2014) Stepwise preparation of all-cis 1,3,4-trifluoro-2-phenylcyclohexane. J Org Chem 79:8228–8233.Google Scholar
  22. 22.
    Keddie NS, Slawin AMZ, Lebl T, Philip D, O’Hagan D (2015) All-cis 1,2,3,4,5,6-hexafluorocyclohexane is a facially polarized cyclohexane. Nature Chem 7:483–488.CrossRefGoogle Scholar
  23. 23.
    Suwada M, Fukuhara T, Hara S (2007) Selective mono-fluorination of diols via a cyclic acetal of N,N-diethyl-4-methoxybenzamide. J Fluorine Chem 128:1121–1125.CrossRefGoogle Scholar
  24. 24.
    Yin JJ, Zarkowsky DS, Thomas DW, Zhao MM, Huffmann MA (2009) Direct and convenient conversion of alcohols to fluorides. Org Lett 6:1465–1468.CrossRefGoogle Scholar
  25. 25.
    L’Heureux A, Beaulieu F, Bennett C, Bill DR, Clayton S, LaFlamme F, Mirmehrabi M, Tadayon S, Tovell D, Couturier M (2010) Aminodifluorosulfinium salts: selective fluorination reagents with enhanced thermal stability and ease of handling J Org Chem 75:3401–3411.PubMedPubMedCentralCrossRefGoogle Scholar
  26. 26.
    Gaguon MC, Turgeon B, Savoir JD, Parent JF, Auger M, Paquin JF (2014) Evaluation of the effect of fluorination on the property of monofluorinated dimyristoylphosphatidylcholines. Org Biomol Chem 12:5126–5135.CrossRefGoogle Scholar
  27. 27.
    Ayuba S, Yoneda N, Fukuhara T, Hara S (2002) Fluorination of sulfides using IF5/Et3N∙3HF. Bull Chem Soc Jpn 75:1597–1603, and references cited therein.Google Scholar
  28. 28.
    Leroux F, Garamszegi L, Schlosser M (2002) A simple method for the displacement of bromine by fluorine at tertiary, benzylic or non-classical secondary sites. J Fluorine Chem 117:177–180.CrossRefGoogle Scholar
  29. 29.
    Geary GC, Hope EG, Singh K, Stuart AM (2013) Electrophilic fluorination using a hypervalent iodine reagent derived from fluoride. Chem Commun 49:9263–9265.CrossRefGoogle Scholar
  30. 30.
    Nash TJ, Pattison G (2015) Apparent electrophilic fluorination of 1,3-dicarbonyl compounds using nucleophilic fluoride mediated by PhI(OAc)2. Eur J Org Chem 2015:3779–3786.CrossRefGoogle Scholar
  31. 31.
    Braun M-G, Doyle AG (2013) Palladium-catalyzed allylic C-H fluorination. J Am Chem Soc 135:12990–12993.PubMedCrossRefPubMedCentralGoogle Scholar
  32. 32.
    Liu W, Groves JT (2013) Manganese-catalyzed oxidative benzylic C-H fluorination by fluoride ions. Angew Chem Int Ed 52:6024–6027.CrossRefGoogle Scholar
  33. 33.
    Huang X, Liu W, Hooker JM, Groves JT (2015) Targeted fluorination with the fluoride ion by manganese-catalyzed decarboxylation. Angew Chem Int Ed 54:5241–5245.CrossRefGoogle Scholar
  34. 34.
    Topczewski JJ, Tewson TJ, Nguyen HM (2011) Iridium-catalyzed allylic fluorination of trichloroacetimidates. J Am Chem Soc 133:19318–19321.PubMedCrossRefPubMedCentralGoogle Scholar
  35. 35.
    Zhang Q, Stockdale DP, Mixdorf JC, Topczewski JJ, Nguyen HN (2015) Iridium-catalyzed enantioselective fluorination of racemic, secondary allylic trichloroacetimidates. J Am Chem Soc 137:11912–11915.PubMedCrossRefPubMedCentralGoogle Scholar
  36. 36.
    Mixdorf JC, Sorlin AM, Zhang Q, Nguyen HM (2018) Asymmetric synthesis of allylic fluorides via fluorination of racemic allylic trichloroacetimidates catalyzed by a chiral diene-iridium complex. ACS Catal 8:790–801.CrossRefGoogle Scholar
  37. 37.
    Zhang Q, Mixdorf JC, Reynders GJ, Nguyen HM (2015) Rhodium-catalyzed benzylic fluorination of trichloroacetimidates. Tetrahedron 71:5932–5938.CrossRefGoogle Scholar
  38. 38.
    Zhang Z, Wang F, Mu X, Chen P, Liu G (2013) Copper-catalyzed regioselective fluorination of allylic halides. Angew Chem Int Ed 52:7549–7553.CrossRefGoogle Scholar
  39. 39.
    Fuchigami T (1994) Selective anodic partial fluorination of heteroatom compounds. Rev Heteroatom Chem 10:155–172.Google Scholar
  40. 40.
    Noel M, Suryanarayanan V, Chellammal S (1997) A review of recent developments in the selective electrochemical fluorination of organic compounds. J Fluorine Chem 83:31–40, and references cited therein.CrossRefGoogle Scholar
  41. 41.
    Fuchigami T (1997) Electrolytic partial fluorination of organic compounds. Highly selective direct and indirect anodic monofluorination of heterocyclic compounds. Proc Electrochem Soc 15:65–73.Google Scholar
  42. 42.
    Fuchigami T, Higashia S, Hou YK, Dawood KM (1999) Highly selective direct and indirect anodic monofluorination of heterocyclic compounds. Rev Heteroatom Chem 19:67–78.Google Scholar
  43. 43.
    Khan ZUH, Kong D, Chen Y, Muhammad N, Khan AU, Khan FU, Tahir K, Ahmad A, Wang L, Wan P (2015) Ionic liquids based fluorination of organic compounds using electrochemical method. J Ind Engin Chem 31:26–38.CrossRefGoogle Scholar
  44. 44.
    Meurs JHH, Sopher DW, Eilenberg W (1989) Oxidative Fluorination of Arenes. Angew Chem Int Ed Engl 28:927–928.CrossRefGoogle Scholar
  45. 45.
    Fuchigami T, Tajima T (2007) Highly diastereoselective anodic fluorination, in: Current Fluoroorganic Chemistry, ACS Symposium Series, vol 949, American Chemical Society, Washington, pp 69–82.CrossRefGoogle Scholar
  46. 46.
    Baroux P, Tardivel R, Simonet J (1995) Anodic fluorination of aromatic thioethers substituted by strongly electron-withdrawing groups. Tetrahedron Lett 36:3851–3852.CrossRefGoogle Scholar
  47. 47.
    Waldmann CM, Lebedev A, Allison N, Sadeghis S (2017) An automated synthesizer for electrochemical 18F-fluorination of organic compounds. Appl Radiat Isot 127:245–252.PubMedPubMedCentralCrossRefGoogle Scholar
  48. 48.
    Kienzle GJ, Reischl G, Machulla HJ (2005) Electrochemical radiofluorination. 3. Direct labeling of phenylalanine derivatives with [18F]fluoride after anodic oxidation. J Label Comp Radiopharm 48:259–273.CrossRefGoogle Scholar
  49. 49.
    Dawood KM, Higashira S, Hou Y, Fuchigami T (1999) Electrolytic partial fluorination of organic compounds. 35. Anodic fluorination of 2-pyrimidyl, 2-pyridyl, and 2-quinazolinyl sulfides. J Org Chem 64:7935–7939.CrossRefGoogle Scholar
  50. 50.
    Dawood KM, Fuchigami T (1999) Electrolytic partial fluorination of organic compounds. 31. Regioseective anodic fluorination of 2-quinolyl and 4-(trifluoromethyl)quinolyl sulfides and the factors affecting its optimization. J Org Chem 64:138–143.PubMedCrossRefGoogle Scholar
  51. 51.
    Dawood KM, Higashiya S, Hou Y, Fuchigami T (1999) Electrolytic partial fluorination of organic compounds. Part 29. Anodic mono- and difluorination of 2-benzoxazolyl sulfides. J Fluorine Chem 93:159–164.CrossRefGoogle Scholar
  52. 52.
    Riyadh SM, Ishii H, Fuchigami T (2001) Electrolytic partial fluorination of organic compounds. Part 57. Regioselective anodic monofluorination of nitrogen-containing heterocyclic propargyl sulfides. Tetrahedron 57:8817–8821.CrossRefGoogle Scholar
  53. 53.
    Kuribayashi S, Shida N, Inagi S, Fuchigami T (2016) Synthesis of fluorinated triazole and isoxazole derivatives by electrochemical fluorination. Tetrahedron 72:5343–5349.CrossRefGoogle Scholar
  54. 54.
    Sunaga T, Atobe M, Inagi S, Fuchigami T (2009) Highly efficient and selective electrochemical fluorination of organosulfur compounds in Et3N∙3HF ionic liquid under ultrasonication. Chem Commun 2009:956–958.CrossRefGoogle Scholar
  55. 55.
    Yin B, Inagi S, Fuchigami T (2015) Highly selective electrochemical fluorination of dithioacetal derivatives bearing electron-withdrawing substituents at the position α to the sulfur atom using poly(HF) salts. Beilstein J Org Chem 11:85–91.PubMedPubMedCentralCrossRefGoogle Scholar
  56. 56.
    Hasegawa M, Fuchigami T (2004) Electroorganic reactions in ionic liquids 5. Anodic fluorodesulfurization of phthalide, ethylene carbonate, and glucopyranosides having arylthio groups. Electrochim Acta 49:3367–3372.CrossRefGoogle Scholar
  57. 57.
    Yin B, Inagi S, Fuchigami T (2011) Selective electrochemical fluorodesulfurization of benzo- and pyrido-fused oxazine derivatives using ex-cell halogen mediators. Synthesis 2011:2372–2376.CrossRefGoogle Scholar
  58. 58.
    Kuribayashi S, Kurioka T, Inagi S, Lu HJ, Uang BJ, Fuchigami T (2018) The selective electrochemical fluorination of S-alkylbenzothioate and its derivatives. Beilstein J Org Chem 14:389–396.PubMedPubMedCentralCrossRefGoogle Scholar
  59. 59.
    Fujita T, Fuchigami T (1996) Electrolytic partial fluorination of organic compounds. 20. Electrosynthesis of novel hypervalent iodobenzene chlorofluoride derivatives and its application to indirect anodic gem-difluorination. Tetrahedron Lett 37:4725–4728.CrossRefGoogle Scholar
  60. 60.
    Böhm S, in: Houben-Weyl – Methods of Organic Chemistry, vol. E10b, Baasner B, Hagemann H, Tatlow JT, Eds., Thieme, Stuttgart, 1999, pp 137–158.Google Scholar
  61. 61.
    Miethchen R, Peters D. in: Houben-Weyl – Methods of Organic Chemistry, vol. E10a, Baasner B, Hagemann H, Tatlow JT, Eds., Thieme, Stuttgart, 2000, pp 111–158.Google Scholar
  62. 62.
    Haufe G (2005) Regio- and stereoselective synthesis of vicinal fluorohydrins. J Fluorine Chem 125:875–894.CrossRefGoogle Scholar
  63. 63.
    Haufe G (2006) in: Science of Synthesis, vol 34, Fluorine, Percy J, Ed., Thieme, Stuttgart, pp 345–378.Google Scholar
  64. 64.
    Sattler A, Haufe G (1994) High regioselectivity in the alternative cleavage of terminal epoxides with different sources of nucleophilic fluoride. J Fluorine Chem 69:185–190.CrossRefGoogle Scholar
  65. 65.
    Hunter L, O’Hagan D (2008) Multi-vicinal fluoroalkanes: a new class of organofluorine compounds. Org Biomol Chem 6:2843–2848, and references cited therein.CrossRefGoogle Scholar
  66. 66.
    Akiyama Y, Hiramatsu C, Fukuhara T, Hara S (2006) Selective introduction of a fluorine atom into carbohydrates and a nucleoside by ring-opening fluorination reaction of epoxides. J Fluorine Chem 127:920–923CrossRefGoogle Scholar
  67. 67.
    O’Hagan D (2012) Organofluorine chemistry: synthesis and conformation of vicinal fluoromethylene motifs. J Org Chem 77:3689–3699.PubMedCrossRefGoogle Scholar
  68. 68.
    Brunet VA, Slawin AMZ, O’Hagan D (2009) Three step synthesis of single diastereoisomers of the vicinal trifluoro motif. Beilstein J Org Chem 5:No 61.Google Scholar
  69. 69.
    Farran D, Slawin AMZ, Kirsch P, O’Hagan D (2009) Diastereoselective synthesis of 2,3,4,5,6-pentafluoroheptanes. J Org Chem 74:7168–7171.PubMedCrossRefGoogle Scholar
  70. 70.
    Patel AR, Hu XG, Lawer A, Ahmed MI, Au C, Jwad R, Trinh J, Gonzalez C, Hannah E, Bhadhade MM, Hunter L (2016) Scalable, stereoselective syntheses of α,β-difluoro-γ-amino acids. Tetrahedron 72:3305–3317.CrossRefGoogle Scholar
  71. 71.
    Cheerlavancha R, Lawer A, Cagnes M, Bhadbhade M, Hunter L (2013) Sequential deoxyfluorination approach for the synthesis of protected α,β,γ-trifluoro-δ-amino acids. Organic Lett 15:5562–5565, see also: Cheerlavancha R, Ahmed A, Leung YC, Lawer A, Liu QQ, Cagnes M, Jang HC, Hu XG, Hunter L (2017) Homologated amino acids with three vicinal fluorines poisoned along the backbone: development of a stereoselective synthesis. Beilstein J Org Chem 13:2316–2325.Google Scholar
  72. 72.
    Bresciani S, Lebl T, Slawin AMZ, O’Hagan D (2010) Fluorosugars: synthesis of the 2,3,4-trideoxy-2,3,4-trifluoro hexose analogues of d-glucose and d-altrose and assessment of their erythrocyte transmembrane transport. Chem Commun 46:5434–5436.CrossRefGoogle Scholar
  73. 73.
    Zhang Q, Nguyen HM (2014) Rhodium-catalyzed regioselective opening of vinyl epoxides with Et3N∙3HF reagent – formation of allylic fluorohydrins. Chem Sci 5:291–296.CrossRefGoogle Scholar
  74. 74.
    Zhu J, Tsui GC, Lautens M (2012) Rhodium-catalyzed enantioselective nucleophilic fluorination: ring opening of oxabicyclic alkenes. Angew Chem Int Ed 51:12353–12556.CrossRefGoogle Scholar
  75. 75.
    Wilkinson JA (1992) Recent advances in the selective formation of the C-F bond. Chem Rev. 92:505–519.CrossRefGoogle Scholar
  76. 76.
    Wolfrum P (1999) in Houben-Weyl, Methods of Organic Chemistry, vol E10b/Part 1, Organofluorine Compounds, Baasner B, Hagemann H, Tatlow JC, Eds., Thieme, Stuttgart, pp 308–310.Google Scholar
  77. 77.
    Alvernhe G, Laurent A, Haufe G (1987) Triethylamine tris-hydrofluoride [(C2H5)3N·3HF] – a highly versatile source of fluoride ion for the halofluorination of alkenes. Synthesis 1987:562–564.CrossRefGoogle Scholar
  78. 78.
    Haufe G (2006) Synthesis (of fluoroalkanes) by addition reactions to alkenes, in: Science of Synthesis, vol 34, Fluorine, Percy JM. Editor, Georg Thieme Verlag, Stuttgart, pp 169–223.Google Scholar
  79. 79.
    Haufe G, Weßel U, Schulze K, Alvernhe A (1995) Synthesis of monofluorinated C-4 building blocks based on methallyl chloride. J Fluorine Chem 74:283–291.CrossRefGoogle Scholar
  80. 80.
    Haufe G, Alvernhe G, Laurent A, Ernet T, Goj O, Kröger S, Sattler A (1999) Bromofluorination of alkenes: 1-Bromo-2-fluoro-2-phenylpropane. Organic Syntheses 76:159–165; Coll. Vol. 10:128–132.Google Scholar
  81. 81.
    Piron K, Verniest G, Van Hende E, De Kimpe N (2012) Synthesis of 3-fluoropyrrolidines and 3-fluoroazetidines. ARKIVOC (v):6–15.Google Scholar
  82. 82.
    Van Brabandt W, Verniest G, De Smaele D, Duvey G, De Kimpe N (2006) Synthesis of 3-Fluoroazetidines. J Org Chem 71:7100–7102.PubMedCrossRefGoogle Scholar
  83. 83.
    Van Hende E, Verniest G, Deroose F, Thuring JW, Macdonald G, De Kimpe N (2009) Synthesis of 1-Boc-3-fluoroazetidine-3-carboxylic acid. J Org Chem 74:2250–2253.PubMedCrossRefGoogle Scholar
  84. 84.
    Reinhardt R, Engewald W, Goj O, Haufe G (1994) Enantiomer separation of side-chain fluorinated alkylbenzenes by capillary gas chromatography on cyclodextrin phases. 39:192–199, see also: Goj O (1995) 2-Aryl-2-fluoroalkanoic acids. PhD Thesis, University of Münster, Germany.CrossRefGoogle Scholar
  85. 85.
    Moens M, D’Hooghe M, De Kimpe N (2013) A convenient approach towards the 1-aminomethyl-1-fluorocycloalkane scaffold. Tetrahedron Lett 54:6110–6113.CrossRefGoogle Scholar
  86. 86.
    Verniest G, Piron K, van Hende E, Thuring JW, Macdonald G, Deroose F, De Kimpe N (2010) Synthesis of aminomethylated 4-fluoropiperidines and 3-fluoropyrrolidines. Org Biomol Chem 8:2509–2512.PubMedCrossRefGoogle Scholar
  87. 87.
    Haufe G, Burchardt A (2001) Synthesis of a fluorinated ether lipid analogous to a platelet activating factor. Eur J Org Chem 2001:4501–4507.CrossRefGoogle Scholar
  88. 88.
    Burchard A, Takahashi T, Takeuchi Y, Haufe G (2001) Synthesis of a fluorinated analogue of anti-cancer active ether lipids. J Org Chem 66:2078–2084.CrossRefGoogle Scholar
  89. 89.
    Haufe G, Burchardt A (2002) Improved synthesis of fluorinated analogues of anti-cancer active ether lipids, Synthesis 2002:648–654.CrossRefGoogle Scholar
  90. 90.
    Mekni N, Hedhli A, Baklouti A (2000) Bromofluorination of bis(allyl)polyoxyethylene glycol ethers. J Fluorine Chem 101:1–4.CrossRefGoogle Scholar
  91. 91.
    Kremlev MM, Haufe G (1998) Halofluorination of 1,2-difluoro- 1,2-di (p-tolyl) ethene, 1,2,3,4-tetrafluoro-1,4-di (p-tolyl) butadiene and its nonfluorinated parent compounds. J Fluorine Chem 90:121–127.CrossRefGoogle Scholar
  92. 92.
    Xue C, Jiang X, Fu C, Ma S (2013) C-F bond formation with fluoride anions – highly selective iodofluorination of simple allenes. Chem Commun 49:5651–5653.CrossRefGoogle Scholar
  93. 93.
    Hara S, Nakahigashi J, Ishi-I K, Sawaguchi M, Sakai H, Fukuhara T, Yoneda N (1998) Difluorination of alkenes with iodotoluene difluoride. Synlett 1998:495–496.CrossRefGoogle Scholar
  94. 94.
    Ye CF, Twamley B, Shreeve JM (2005) Straightforward syntheses of hypervalent Iodine(III) reagents mediated by Selectfluor. Org Lett 7:3961–3964.PubMedCrossRefGoogle Scholar
  95. 95.
    Molnár GI, Gilmour R (2016) Catalytic difluorination of olefins. J Am Chem Soc 138:5004–5007.PubMedCrossRefGoogle Scholar
  96. 96.
    Banik SM, Medley JW, Jacobsen EJ (2016) Catalytic diastereoselective 1,2-difluorination of alkenes. J Am Chem Soc 138:5000–5003.PubMedPubMedCentralCrossRefGoogle Scholar
  97. 97.
    Uneyama K, Asai H, Dan-oh Y, Matta H (1997) Electrochemical generation of [PhSeF] for fluoro-selenation of alkenes and alkynes and its recycle use. Electrochim Acta 42:2005–2007.CrossRefGoogle Scholar
  98. 98.
    Lu DF, Liu GS, Zhu CL, Yuan B, Xu H (2014) Iron(II)-catalyzed intramolecular olefin aminofluorination. Org Lett 16:2912–2015.PubMedCrossRefGoogle Scholar
  99. 99.
    Saavedra-Olavarría J, Arteaga GC, López JJ, Pérez EG (2015) Copper-catalyzed intermolecular and regioselective aminofluorination of styrenes: facile access to β-fluoro-N-protected phenethylamines. Chem Commun 51:3379–3382.CrossRefGoogle Scholar

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Authors and Affiliations

  1. 1.Organic Chemistry InstituteUniversity of MünsterMünsterGermany