Abstract
Fluorination of ketones was achieved by the reaction of silyl enol ethers with iodotoluene difluoride in the presence of BF3 ·OEt2 and a Et3 N·HF complex.
Key words
fluorination - iodotoluene difluoride - silyl enol ether - ketone - hypervalent iodine
References
1 Rozen S.
Filler R.
Tetrahedron
1985,
41:
1111
2 Welch JT.
Eswarakrishnan S.
Fluorine in Bioorganic Chemistry
Wiley;
New York:
1991.
3 Taylor SD.
Kotoris CC.
Hum G.
Tetrahedron
1999,
55:
12431
4 Hara S.
Sekiguchi M.
Ohmori A.
Fukuhara T.
Yoneda N.
Chem. Commun.
1996,
1899
5 Yoshida M.
Fujikawa K.
Sato S.
Hara S.
Arkivoc
2003,
vi:
36 ; www.arkat-usa.org
6 Carpenter W.
J. Org. Chem.
1966,
31:
2688
7 Sawaguchi M.
Ayuba S.
Hara S.
Synthesis
2002,
1802
8 Greaney MF.
Motherwell WB.
Tetrahedron Lett.
2000,
41:
4463
9 Greaney MF.
Motherwell WB.
Tetrahedron Lett.
2000,
41:
4467
10 Greaney MF.
Motherwell WB.
Tocher DA.
Tetrahedron Lett.
2001,
42:
8523
11 Motherwell WB.
Greaney MF.
Tocher DA.
J. Chem. Soc., Perkin Trans. 1
2002,
2809
12 Tsushima T.
Kawada K.
Tsuji T.
Tetrahedron Lett.
1982,
23:
1165
13 5 in good yields by this method: Zefirov NS.
Samoniya NS.
Kutateladze TG.
Zhdankin VV.
Zh. Org. Khim.
1991,
27:
220 ; Chem. Abstr.
1991,
115:
91694
14 McClinton MA.
Aldrichimica Acta
1995,
28:
75
15 Haufe G.
J. Prakt. Chem.
1996,
338:
99
16 Rozen S.
Menahem Y.
J. Fluorine Chem.
1980,
16:
19
17 Thomas MG.
Suckling CJ.
Pitt AR.
Suckling KE.
J. Chem. Soc., Perkin Trans. 1
1999,
3191
18 Stavber S.
Jereb M.
Zupan M.
Synthesis
2002,
2609
19 An equilibrium between two isomers of 7 was not observed under the reaction conditions.
20 Eames J.
Coumbarides GS.
Suggate MJ.
Weerasooriya N.
Eur. J. Org. Chem.
2003,
634
21 A centrifuge tube with a screw cap made of Teflon FEP, a copolymer of TFE and hexafluoropropylene, was used.
22 Cousseau J.
Albert P.
J. Org. Chem.
1989,
54:
5380
23 Stavber S.
Sket B.
Zajc B.
Zupan M.
Tetrahedron
1989,
45:
6003
