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Halogenated Heterocycles pp 1–31Cite as

Perfluoroheteroaromatic Chemistry: Multifunctional Systems from Perfluorinated Heterocycles by Nucleophilic Aromatic Substitution Processes

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Part of the book series: Topics in Heterocyclic Chemistry ((TOPICS,volume 27))

Abstract

Perfluoroheteroaromatic systems, such as pentafluoropyridine, tetrafluoropyrazine and tetrafluoropyridazine, are highly electrophilic due to the presence of several fluorine atoms attached to the heteroaryl rings and, consequently, react very readily with a wide range of nucleophilic species. In this chapter, we discuss reports of recent nucleophilic aromatic substitution reactions of perfluoroheteroaromatic substrates that have enabled the synthesis of, for example, a wide range of highly functionalised heterocyclic derivatives, macrocycles, ring-fused systems and glycosyl donors.

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Abbreviations

d:

Day

DIPEA:

Diisopropylethylamine

DMEU:

N, N-Dimethylethylene urea

DMF:

N,N-Dimethyl formamide

LDA:

Lithium diisopropylamine

MeCN:

Acetonitrile

MW:

Microwave irradiation

Nuc:

Nucleophile

rt:

Room temperature

SEM:

(Trimethylsilyl)ethoxymethyl

TDAE:

Tetrakis(dimethylamino)ethylene

THF:

Tetrahydrofuran

THP:

Tetrahydropyran

TMEDA:

Tetramethylethylene diamine

References

  1. Katritzky AR, Rees CW (1984) Comprehensive heterocyclic chemistry. Pergamon, Oxford

    Google Scholar 

  2. Pozharskii AF, Soldantenkov AT, Katritzky AR (1997) Heterocycles in life and society. Wiley, New York

    Google Scholar 

  3. Chambers RD, Sargent CR (1981) Adv Heterocycl Chem 28:1–71

    Article  CAS  Google Scholar 

  4. Brooke GM (1997) J Fluor Chem 86:1–76

    Article  Google Scholar 

  5. Chambers RD, Hutchinson J, Musgrave WKR (1964) J Chem Soc:3573–3576

    Google Scholar 

  6. Silvester MJ (1994) Adv Heterocycl Chem 59:1–37

    Article  CAS  Google Scholar 

  7. Chambers RD (2004) Fluorine in organic chemistry. Blackwell, Oxford

    Book  Google Scholar 

  8. Baasner B, Hagemann H, Tatlow JC (2000) Houben-Weyl organo fluorine compounds, vol E10. Thieme, Stuttgart

    Google Scholar 

  9. Uneyama K (2006) Organofluorine chemistry. Blackwell, Oxford

    Book  Google Scholar 

  10. Shaub T, Fischer P, Steffen A, Braun T, Radius U, Mix A (2008) J Am Chem Soc 130:9304–9317

    Article  Google Scholar 

  11. Braun T, Wehmeier F (2011) Eur J Inorg Chem: 613–625.

    Google Scholar 

  12. Olah GA, Molnar A (1995) Hydrocarbon Chemistry. Wiley, New York

    Google Scholar 

  13. Chambers RD, Waterhouse JS, Williams DLH (1977) J Chem Soc Perkin 2:585–588

    Google Scholar 

  14. Chambers RD, Martin PA, Sandford G, Williams DLH (2008) J Fluor Chem 129:998–1002

    Article  CAS  Google Scholar 

  15. Baker J, Muir M (2010) Can J Chem 88:588–597

    Article  CAS  Google Scholar 

  16. Murray CB, Sandford G, Korn SR, Yufit DS, Howard JAK (2005) J Fluor Chem 126:571–576

    Article  Google Scholar 

  17. Lork E, Mews R, Shakirov MM, Watson PG, Zibarev AV (2002) J Fluor Chem 115:165–168

    Article  CAS  Google Scholar 

  18. Beletskaya IP, Artamkina GA, Ivushkin VA, Guilard R (2000) Tetrahedron Lett 41:313–316

    Article  CAS  Google Scholar 

  19. Artamkina GA, Tarasenko EA, Lukashev NV, Beletskaya IP (1998) Tetrahedron Lett 39:901–904

    Article  CAS  Google Scholar 

  20. Wang Y, Parkin SR, Watson MD (2008) Org Lett 10:4421–4424

    Article  CAS  Google Scholar 

  21. Tyrra W, Naumann D, Hoge B, Yagupolskii YL (2003) J Fluor Chem 119:101–107

    Article  CAS  Google Scholar 

  22. Hargreaves CA, Sandford G, Slater R, Yufit D, Howard JAK, Vong A (2007) Tetrahedron 63:5204–5211

    Article  CAS  Google Scholar 

  23. Zeika O, Li Y, Jockusch S, Parkin G, Sattler A, Sattler W, Turro NJ (2010) Org Lett 12:3696–3699

    Article  CAS  Google Scholar 

  24. Kusov SZ, Rodionov VI, Vaganova TA, Shundrina IK, Malykhin EV (2009) J Fluor Chem 130:461–465

    Article  CAS  Google Scholar 

  25. Cornago P, Escolastico C, Santa Maria MD, Claramunt RM, Fernandez-Castano C, Foces-Foces C, Fayet JP, Elguero J (1996) Tetrahedron 52:11075–11094

    Article  CAS  Google Scholar 

  26. Huchel U, Schmidt C, Schmidt RR (1998) Eur J Org Chem 7:1353–1360

    Article  Google Scholar 

  27. Hargreaves CA, Sandford G, Davis BG (2007) Fluorinated synthons. In: Soloshonok VA (ed) ACS Symposium Series 949. ACS, Washington DC, p 323–336

    Google Scholar 

  28. Christopher JA, Brophy L, Lynn SM, Miller DD, Sloan LA, Sandford G (2008) J Fluor Chem 129:447–454

    Article  CAS  Google Scholar 

  29. Chambers RD, Hoskin PR, Sandford G, Yufit DS, Howard JAK (2001) J Chem Soc Perkin Trans 1:2788–2795

    Google Scholar 

  30. Benmansour H, Chambers RD, Sandford G, McGowan G, Dahaoui S, Yufit DS, Howard JAK (2001) J Fluor Chem 112:349–355

    Article  CAS  Google Scholar 

  31. Lipinski CA, Lombardo F, Dominy BW, Feeney PJ (1997) Adv Drug Deliv Rev 23:3–25

    Article  CAS  Google Scholar 

  32. Collins I (2000) J Chem Soc Perkin Trans 1:2845–2861

    Google Scholar 

  33. Collins I (2002) J Chem Soc Perkin Trans 1:1921–1940

    Google Scholar 

  34. Davie EW, Fujikawa K, Kisiel W (1991) Biochemistry 30:10363–10370

    Article  CAS  Google Scholar 

  35. Kranjc A, Kikelj D, Peterlin-Masic L (2005) Curr Pharm Des 11:4207–4227

    Article  CAS  Google Scholar 

  36. Walenga JM, Jeske WP, Hoppensteadt D, Fareed J (2003) Curr Opin Invest Drugs 4:272–281

    CAS  Google Scholar 

  37. Ng HP, Buckman BO, Eagen KA, Guilford WJ, Kochanny MJ, Mohan R, Shaw KJ, Wu SC, Lentz D, Liang A, Ho LTE, Smith D, Subramanyam B, Vergona R, Walters J, White KA, Sullivan ME, Morrissey MM, Phillips GB (2002) Bioorg Med Chem 10:657–666

    Article  CAS  Google Scholar 

  38. Revesz L, Padova FED, Buhl T, Feifel R, Gram H, Hiestand P, Manning U, Wolf R, Zimmerlin AG (2002) Bioorg Med Chem Lett 12:2109–2112

    Article  CAS  Google Scholar 

  39. Parks EL, Sandford G, Yufit DS, Howard JAK, Christopher JA, Miller DD (2010) Tetrahedron 66:6195–6204

    Article  CAS  Google Scholar 

  40. Pattison G, Sandford G, Yufit DS, Howard JAK, Christopher JA, Miller DD (2009) J Org Chem 74:5533–5540

    Article  CAS  Google Scholar 

  41. Pattison G, Sandford G, Yufit DS, Howard JAK, Christopher JA, Miller DD (2009) Tetrahedron 65:8844–8850

    Article  CAS  Google Scholar 

  42. Gutov AV, Rusanov EB, Ryabitskii AB, Chernega AN (2010) J Fluor Chem 131:278–281

    Article  CAS  Google Scholar 

  43. Lehn JM, Atwood JL, Davies JED, MacNicol DD, Votgle F (1996) Comprehensive supramolecular chemistry, vol 1–11. OUP, Oxford

    Google Scholar 

  44. Schneider HJ, Yatsimirsky AK (2000) Principles and methods in supramolecular chemistry. Wiley, New York

    Google Scholar 

  45. Sandford G (2003) Chem Eur J 9:1464–1469

    Article  CAS  Google Scholar 

  46. Chambers RD, Hoskin PR, Kenwright AR, Khalil A, Richmond P, Sandford G, Yufit DS, Howard JAK (2003) Org Biomol Chem 1:2137–2147

    Article  CAS  Google Scholar 

  47. Chambers RD, Khalil A, Richmond P, Sandford G, Yufit DS, Howard JAK (2004) J Fluor Chem 125:715–720

    Article  CAS  Google Scholar 

  48. Hope EG, Stuart AM (2000) Adv Inorg Fluorides:403–436.

    Google Scholar 

  49. Horvath IT (1998) Acc Chem Res 31:641–650

    Article  CAS  Google Scholar 

  50. Ranjbar-Karimi R, Sandford G, Yufit DS, Howard JAK (2008) J Fluor Chem 129:307–313

    Article  CAS  Google Scholar 

  51. Beer PD, Gale PA (2001) Angew Chem Int Ed Engl 40:486–516

    Article  CAS  Google Scholar 

  52. Sandford G, Slater R, Yufit DS, Howard JAK, Vong A (2005) J Org Chem 70:7208–7216

    Article  CAS  Google Scholar 

  53. Pattison G, Sandford G, Yufit DS, Howard JAK, Christopher JA, Miller DD (2010) Beilstein J Org Chem 6:45

    Article  Google Scholar 

  54. Cartwright MW, Sandford G, Yufit DS, Howard JAK, Christopher JA, Miller DD (2007) Tetrahedron 63:7027–7035

    Article  CAS  Google Scholar 

  55. Cartwright MW, Convery L, Kraynck T, Sandford G, Yufit DS, Howard JAK, Christopher JA, Miller DD (2010) Tetrahedron 66:519–529

    Article  CAS  Google Scholar 

  56. Parks EL, Sandford G, Yufit DS, Howard JAK, Christopher JA, Miller DD (2010) J Fluor Chem 131:1086–1090

    Article  CAS  Google Scholar 

  57. Cartwright MW, Parks EL, Pattison G, Slater R, Sandford G, Wilson I, Yufit DS, Howard JAK, Christopher JA, Miller DD (2010) Tetrahedron 66:3222–3227

    Article  CAS  Google Scholar 

  58. Baron A, Sandford G, Slater R, Yufit DS, Howard JAK, Vong A (2005) J Org Chem 70:9377–9381

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Department of Chemistry, Durham University, South Road, Durham, DH1 3LE, UK

    Graham Sandford

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  1. Graham Sandford
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Correspondence to Graham Sandford .

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Editors and Affiliations

  1. , Department of Physical and Organic Chemi, "Jozef Stefan" Institute, Jamova 39, Ljubljana, 1000, Slovenia

    Jernej Iskra

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Sandford, G. (2011). Perfluoroheteroaromatic Chemistry: Multifunctional Systems from Perfluorinated Heterocycles by Nucleophilic Aromatic Substitution Processes. In: Iskra, J. (eds) Halogenated Heterocycles. Topics in Heterocyclic Chemistry, vol 27. Springer, Berlin, Heidelberg. https://doi.org/10.1007/7081_2011_63

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