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DOI: 10.1055/s-0030-1258330
Novel Introduction of a Tetrafluoroethylene (-CF2CF2-) Unit into Organic Molecules
Publication History
Publication Date:
15 November 2010 (online)
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Abstract
The reductive coupling of 4-bromo-3,3,4,4-tetrafluorobut-1-ene with 2.4 equivalents of various carbonyl compounds proceeded very smoothly in the presence of 2.4 equivalents of MeLi/LiBr-free at -78 ˚C for two hours, giving the corresponding adducts in high to excellent yields. On the other hand, triethyl(1,1,2,2-tetrafluorobut-3-enyl)silane, which could be prepared by treatment of 4-bromo-3,3,4,4-tetrafluorobut-1-ene and chlorotriethylsilane with magnesium at 0 ˚C for three hours, reacted with some aldehydes in the presence of 1 mol% of tetrabutylammonium fluoride, the desired adducts being obtained in good to high yields.
Key words
tetrafluoroethylene - MeLi/LiBr-free - triethyl(1,1,2,2-tetrafluorobut-3-enyl)silane - reductive coupling
-
1a
Purser S.Moore PR.Swallow S.Gouverneur V. Chem. Soc. Rev. 2008, 37: 320 -
1b
O’Hagan D. Chem. Soc. Rev. 2008, 37: 308 -
1c
Müller K.Faeh C.Diederich F. Science 2007, 317: 1881 -
1d
Kirk KL. J. Fluorine Chem. 2006, 127: 1013 -
1e
Bégué JP.Bonnet-Delpon D. J. Fluorine Chem. 2006, 127: 992 -
1f
Isanbor C.O’Hagan D. J. Fluorine Chem. 2006, 127: 303 -
1g
O’Hagen D.Rzepa H. Chem. Commun. 1997, 645 -
1h
Biomedical Frontiers
of Fluorine Chemistry
Ojima I.McCarthy JR.Welch JT. American Chemical Society; Washington DC: 1996. -
1i
Mann J. Chem. Soc. Rev. 1987, 16: 381 -
1j
Welch JT. Tetrahedron 1987, 43: 3123 -
2a
Uno H.Okada S.Ono T.Shiraishi Y.Suzuki H.
J. Org. Chem. 1992, 57: 1504 -
2b
Uneyama K.Kitagawa K. Tetrahedron Lett. 1991, 32: 375 -
2c
Uneyama K.Kitagawa K. Tetrahedron Lett. 1991, 32: 3385 -
2d
Gassman PG.O’Reilly NJ. J. Org. Chem. 1987, 52: 2481 -
3a
Biffinger JC.Kim HW.DiMagno SG. ChemBioChem 2004, 5: 622 -
3b
Kim HW.Rossi P.Shoemaker RK.DiMagno SG. J. Am. Chem. Soc. 1998, 120: 9082 -
4a
Timofte RS.Linclau B. Org. Lett. 2008, 10: 3673 -
4b
Boydell AJ.Vinader V.Linclau B. Angew. Chem. Int. Ed. 2004, 43: 5677 - 5
Bonnac L.Lee SE.Giuffredi GT.Elphick LM.Anderson AA.Child ES.Mann DJ.Gouverneur V. Org. Biomol. Chem. 2010, 8: 1445 - The absolute stereochemistry was determined on the basis of the stereochemical outcome in the reaction of the chiral sulfinimines with various organometallics. See:
-
7a
Li Y.Ni C.Liu J.Zhang L.Zheng J.Zhu L.Hu J. Org. Lett. 2006, 8: 1693 -
7b
Liu G.Cogan DA.Ellman JA.
J. Am. Chem. Soc. 1997, 119: 9913 -
8a
Prakash GKS.Yudin AK. Chem. Rev. 1997, 97: 757 -
8b
Singh RP.Shreeve JM. Tetrahedron 2000, 56: 7613 - There has been no report on the synthesis of unsymmetric 2,2,3,3-tetrafluoro-1,4-diol derivatives. Two references, in which symmetric 2,2,3,3-tetrafluoro-1,4-diol derivatives were synthesized, have been published thus far.
-
9a
Fuchigami T, andHagiwara T. inventors; JP 6228030. -
9b
Dormidontov YP.Shadrina LP. Zh. Org. Khim. 1983, 19: 269
References
Unpublished results.