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Synthesis 2005(18): 3140-3146
DOI: 10.1055/s-2005-918424
DOI: 10.1055/s-2005-918424
PAPER
© Georg Thieme Verlag Stuttgart · New York
Efficient Synthesis of α,α-Difluoro Ketones Using SelectfluorTM F-TEDA-BF4
Further Information
Received
30 May 2005
Publication Date:
06 October 2005 (online)
Publication History
Publication Date:
06 October 2005 (online)
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Abstract
Selective and efficient synthesis of α,α-difluoro ketones was achieved following a protocol which includes the transformation of α-methylene ketones to the corresponding n-butylimine derivatives and their further treatment with SelectfluorTM F-TEDA-BF4 in acetonitrile solution at 80 °C.
Key words
halogenation - fluorination - imines - ketones - α,α-difluoro ketones - Selectfluor F-TEDA-BF4
- 1
Smart BE. J. Fluorine Chem. 2001, 109: 3 -
2a
Chemistry of Organic Fluorine Compounds II: A Critical Review, ACS Monograph 187
Hudlicky M.Pavlath AE. American Chemical Society; Washington, DC: 1995. -
2b
Modern Fluoroorganic Chemistry. Synthesis, Reactivity, Applications
Kirsch P. Wiley-VCH; Weinheim: 2004. -
2c
Chambers RD. Fluorine in Organic Chemistry Blackwell; Oxford: 2004. - 2d ChemBioChem, Special Issue on Fluorine in Life Sciences Vol. 37: Royal Society of Chemistry; Cambridge: 2004. p.557-726
- 3
Methods of Organic Chemistry (Houben-Weyl), Organofluorine Compounds
Baasner B.Hagemann H.Tatlow JC. Vol. E 10a-c; Thieme: Stuttgart: 1999. - 4
Shimizu M.Hiyama T. Angew. Chem. Int. Ed. 2005, 44: 214 - 5
Gelb MH.Svaren JP.Abeles RH. Biochemistry 1985, 24: 1813 - 6
Tarnus C.Jung MJ.Remy JM.Baltzer S.Schirlin DG. FEBS Lett. 1989, 249: 47 - 7
Sham HL.Stein H.Rempel CA.Cohen J.Plattner JJ. FEBS Lett. 1987, 220: 299 - 8
Thaisrivongs S.Pals DT.Kati WM.Turner SR.Thomasco LM.Watt W. J. Med. Chem. 1986, 29: 2080 - 9
Takahashi LH.Radhakrishnan R.Rosenfield RE.Meyer EF.Trainor DA. J. Am. Chem. Soc. 1989, 111: 3368 - 10
Imperiali B.Abeles RH. Biochemistry 1987, 26: 4474 - 11
Imperiali B.Abeles RH. Biochemistry 1986, 25: 3760 - 12
Robinson RP.Donahue KM. J. Org. Chem. 1992, 57: 7309 - 13
Sham HL.Betebenner DA.Wideburg NE.Kempf DJ.Plattner JJ.Norbeck DW. J. Fluorine Chem. 1995, 73: 221 - 14
Wolfe MS.Xia WM.Moore CL.Leatherwood DD.Ostaszewski B.Rahmati T.Donkor IO.Selkoe DJ. Biochemistry 1999, 38: 4720 - 15
Moore CL.Leatherwood DD.Diehl TS.Selkoe DJ.Wolfe MS. J. Med. Chem. 2000, 43: 3434 - 16
Wolfe MS.Citron M.Diehl TS.Xia WM.Donkor IO.Selkoe DJ. J. Med. Chem. 1998, 41: 6 - 17
Reiter LA.Martinelli GJ.Reeves LA.Mitchell PG. Bioorg. Med. Chem. Lett. 2000, 10: 1581 - 18
Biomedical Frontiers of Fluorine Chemistry
Ojima I.McCarthy JR.Wolfe MS. American Chemical Society; Washington DC: 1996. - 19
Stavber S.Zupan M. J. Org. Chem. 1987, 52: 5022 - 20
Zupan M.Iskra J.Stavber S. J. Org. Chem. 1995, 60: 259 - 21
Stavber S.Zupan M. Synlett 1996, 693 - 22
Zajc B.Zupan M. J. Org. Chem. 1982, 47: 573 - 23
Umemoto T.Fukami S.Tomizawa G.Harasawa K.Kawada K.Tomita K. J. Am. Chem. Soc. 1990, 112: 8563 - 24
Xu ZQ.DesMarteau DD.Gotoh Y. J. Fluorine Chem. 1992, 58: 71 - 25
Davis FA.Han W.Murphy CK. J. Org. Chem. 1995, 60: 4730 - 26
Banks RE.Lawrence NJ.Popplewell AL. J. Chem. Soc., Chem. Commun. 1994, 343 - 27
Stavber G.Zupan M.Jereb M.Stavber S. Org. Lett. 2004, 6: 4973 - 28
Stavber S.Jereb M.Zupan M. Synthesis 2002, 2609 - 29
Tozer MJ.Herpin TF. Tetrahedron 1996, 52: 8619 - 30
Stavber S.Jereb M.Zupan M. Chem. Commun. 2000, 1323 -
31a
Nakano T.Makino M.Morizawa Y.Matsumura Y. Angew. Chem. Int. Ed. 1996, 35: 1019 -
31b
Thomas MG.Suckling CJ.Pitt AR.Suckling KE. J. Chem. Soc., Perkin Trans.1 1999, 3191 - 32
Ying WW.DesMarteau DD.Gotoh Y. Tetrahedron 1996, 52: 15 - 33
Peng W.Shreeve JM. J. Org. Chem. 2005, 70: 5760 - 34
Gutman AL.Etinger M.Nisnevich G.Polyak F. Tetrahedron: Asymmetry 1998, 9: 4369 - 35
Johnson GP.Marples BA. Tetrahedron Lett. 1984, 25: 3359 - 36
Warmuth R.Munsch TE.Stalker RA.Li B.Beatty A. Tetrahedron 2001, 57: 6383 - 37
Gilicinski AG.Pez GP.Syvret RG.Lal GS. J. Fluorine Chem. 1992, 59: 157 - 38
Singh RP.Shreeve JM. Acc. Chem. Res. 2004, 37: 31 - 39
Stavber S.Zupan M. Acta Chim. Slov. 2005, 52: 13 - 40
Appelman EH.Basile LJ.Thompson RC. J. Am. Chem. Soc. 1979, 101: 3384