Highly efficient Pd-catalyzed coupling of arenes with olefins in the presence of tert-butyl hydroperoxide as oxidant

被引:244
作者
Jia, CG [1 ]
Lu, WJ [1 ]
Kitamura, T [1 ]
Fujiwara, Y [1 ]
机构
[1] Kyushu Univ, Grad Sch Engn, Dept Chem & Biochem, Fukuoka 8128581, Japan
关键词
D O I
10.1021/ol991148u
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] ArH : benzoid and non-benzoid. R = H, CH3, Ph. R-1 = Ph, Co2Et, COMe, CHO, CO2H, CN. The oxidative coupling of arenes with olefins has been performed efficiently in the presence of catalytic amounts of palladium acetate and benzoquinone (BQ) with tert-butyl hydroperoxide as the oxidant in up to 280 turnover numbers (TON). The catalytic system is especially active for the coupling of heterocycles such as furans and indole with activated olefins, The reaction is highly regio- and stereoselective, giving trans-olefins predominantly.
引用
收藏
页码:2097 / 2100
页数:4
相关论文
共 21 条
[1]  
AKERMARK B, 1994, J ORG CHEM, V59, P5729
[2]  
Asano R., 1970, CHEM COMMUN, P1293
[3]   ACTIVATION OF AROMATIC CARBON HYDROGEN-BONDS BY PALLADIUM(II) ACETATE-DIALKYL SULFIDE SYSTEMS - FORMATION AND CHARACTERIZATION OF NOVEL DIPHENYLTRIPALLADIUM(II)COMPLEXES [J].
FUCHITA, Y ;
HIRAKI, K ;
KAMOGAWA, Y ;
SUENAGA, M ;
TOHGOH, K ;
FUJIWARA, Y .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1989, 62 (04) :1081-1085
[4]   AROMATIC SUBSTITUTION OF OLEFINS .6. ARYLATION OF OLEFINS WITH PALLADIUM(II) ACETATE [J].
FUJIWARA, Y ;
MORITANI, I ;
DANNO, S ;
ASANO, R ;
TERANISH.S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1969, 91 (25) :7166-&
[5]   Exploitation of synthetic reactions via C-H bond activation by transition metal catalysts. Carboxylation and aminomethylation of alkanes or arenes [J].
Fujiwara, Y ;
Takaki, K ;
Taniguchi, Y .
SYNLETT, 1996, (07) :591-&
[6]  
Fujiwara Y., 1976, J ORG CHEM, V41, P1681
[7]  
FUJIWARA Y, 1990, CHEMTECH, P636
[8]   ACID-INDUCED TRANSFORMATION OF PALLADIUM(0) BENZOQUINONE COMPLEXES TO PALLADIUM(II) AND HYDROQUINONE [J].
GRENNBERG, H ;
GOGOLL, A ;
BACKVALL, JE .
ORGANOMETALLICS, 1993, 12 (05) :1790-1793
[9]   PALLADIUM-CATALYZED ALLYLIC ACETOXYLATION OF OLEFINS USING HYDROGEN-PEROXIDE AS OXIDANT [J].
JIA, CG ;
MULLER, P ;
MIMOUN, H .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1995, 101 (02) :127-136
[10]   Addition of olefins to aromatic ketones catalyzed by Rh(I) olefin complexes [J].
Lenges, CP ;
Brookhart, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (28) :6616-6623