Nickel catalyzed hydrovinylation of arylethylenes:: General method of synthesis of α-arylpropionic acids intermediates

被引:31
作者
Fassina, V [1 ]
Ramminger, C [1 ]
Seferin, M [1 ]
Monteiro, AL [1 ]
机构
[1] Univ Fed Rio Grande Sul, Inst Quim, BR-91591970 Porto Alegre, RS, Brazil
关键词
nickel; hydrovinylation; alpha-arylpropionic acids; codimerization; styrene;
D O I
10.1016/S0040-4020(00)00668-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The hydrovinylation of arylethylenes catalyzed by [Ni(MeCN)(6)][BF4](2)/AIEt(2)Cl/PPh3 was modulated to obtain 3-aryl-1-butenes in high yields and selectivities. A wide variety of arylethylenes containing electron-donating or electron-withdrawing groups and Lewis basic group, can be hydrovinylated at room temperature and under mild conditions by changing the relative ratios of the three-component catalyst. Similar activities and selectivities were observed for o-, m- and p-substituted styrenes. Also, the hydrovinylation of olefins with substituents in the vinyl fragment, such as ol-methylstyrene and indene, can be accomplished. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:7403 / 7409
页数:7
相关论文
共 26 条
[1]   OLEFIN-TO-OLEFIN ADDITION REACTIONS [J].
ALDERSON, T ;
JENNER, EL ;
LINDSEY, RV .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (24) :5638-&
[2]   CATIONIC BENZYL NICKEL-COMPLEXES AS HOMOGENEOUS CATALYSTS FOR STYRENE OLIGOMERIZATION - X-RAY CRYSTAL-STRUCTURE OF [NI(ETA-3-CH2C6H5)(PPH3)2]PF6.CH2CL2 [J].
ASCENSO, JR ;
CARRONDO, MAA ;
DIAS, AR ;
GOMES, PT ;
PIEDADE, MFM ;
ROMAO, CC ;
REVILLON, A ;
TKATCHENKO, I .
POLYHEDRON, 1989, 8 (20) :2449-2457
[3]  
ASCENSO JR, 1989, MACROMOLECULES, V22, P1000
[4]   Asymmetric hydrovinylation of styrene applying cationic allyl palladium complexes of a P-chiral ligand - Prof Dr Drhc Friedrich Asinger on the occasion of his 90th birthday [J].
Bayersdorfer, R ;
Ganter, B ;
Englert, U ;
Keim, W ;
Vogt, D .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1998, 552 (1-2) :187-194
[5]   HYDROVINYLATION OF STYRENE DERIVATIVES TO 3-ARYL-1-BUTENES CATALYZED BY NICKEL-COMPLEXES [J].
CEDER, R ;
MULLER, G ;
ORDINAS, JI .
JOURNAL OF MOLECULAR CATALYSIS, 1994, 92 (02) :127-139
[6]   Heterodimerization of propylene and vinylarenes: Functional group compatibility in a highly efficient Ni-catalyzed carbon-carbon bond-forming reaction [J].
Jin, J ;
RajanBabu, TV .
TETRAHEDRON, 2000, 56 (15) :2145-2151
[7]  
Jolly P.W., 1996, Applied Homogeneous Catalysis with Organometallic Compounds, V2, P1024
[8]   CODIMERIZATION OF ETHYLENE AND STYRENE CATALYZED BY BIS(TRIPHENYLPHOSPHINE)-SIGMA-ARYLNICKEL(II) HALIDE-TRIFLUOROBORON ETHERATE [J].
KAWATA, N ;
MARUYA, K ;
MIZOROKI, T ;
OZAKI, A .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1974, 47 (02) :413-416
[9]   Synthesis of 3-aryl-1-butenes by the nickel catalyzed hydrovinylation of styrene derivatives [J].
Monteiro, AL ;
Seferin, M ;
Dupont, J ;
deSouza, RF .
TETRAHEDRON LETTERS, 1996, 37 (08) :1157-1160
[10]   Hydrovinylation of olefins catalyzed by cationic nickel complexes [Ni(2,4,6-Me3C6H2)(CH3CN)P-2]BF4 [J].
Muller, G ;
Ordinas, JI .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1997, 125 (2-3) :97-108