Rhodium-catalyzed α-fluoroalkylation reaction of ketones using silyl enol ethers

被引:32
作者
Sato, Kazuyuki [1 ]
Higashinagata, Makoto [1 ]
Yuki, Takashi [1 ]
Tarui, Atsushi [1 ]
Omote, Masaaki [1 ]
Kumadaki, Itsumaro [1 ]
Ando, Akira [1 ]
机构
[1] Setsunan Univ, Fac Pharmaceut Sci, Osaka 5730101, Japan
关键词
fluorine; rhodium; silyl enol ethers; alpha-fluoroalkylation;
D O I
10.1016/j.jfluchem.2007.08.013
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The treatment of silyl enol ethers with fluoroalkyl halides (R-f-X) in the presence of RhCl(PPh3)(3) gave alpha-fluoroalkylated ketones. It seems that a rhodium complex derived from the silyl enol ether and RhCl(PPh3)(3) played an important role for the oxidative addition of fluoroalkyl halides and the reductive elimination of the product. (C) 2007 Elsevier B.V. All rights reserved.
引用
收藏
页码:51 / 55
页数:5
相关论文
共 18 条
[1]  
[Anonymous], 1998, TRANSITION METALS OR
[2]  
EVANS PA, 2005, MODEM RHODIUM CATALY
[3]   Rhodium-catalyzed carbon-carbon bond forming reactions of organometallic compounds [J].
Fagnou, K ;
Lautens, M .
CHEMICAL REVIEWS, 2003, 103 (01) :169-196
[4]  
Filler R., 1993, ORGANOFLUORINE COMPO
[5]  
Hayashi T, 2001, SYNLETT, P879
[6]   Rhodium-catalyzed asymmetric addition of organo-boron and -titanium reagents to electron-deficient olefins [J].
Hayashi, T .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2004, 77 (01) :13-21
[7]  
Hudlicky M., 1995, CHEM ORGANIC FLUORIN
[8]   ELECTRONEGATIVITY OF GROUPS [J].
HUHEEY, JE .
JOURNAL OF PHYSICAL CHEMISTRY, 1965, 69 (10) :3284-&
[9]  
Miyaura N., 2001, ACS SYM SER, P94
[10]   Rhodium-catalyzed novel trifluoromethylation at the α-position of α-β-unsaturated ketones [J].
Sato, K ;
Omote, M ;
Ando, A ;
Kumadaki, I .
ORGANIC LETTERS, 2004, 6 (23) :4359-4361