SELECTIVE MONOALKYLATION AND MONOARYLATION OF DICHLOROBENZENES BY PALLADIUM-CATALYZED GRIGNARD CROSS-COUPLING

被引:25
作者
KATAYAMA, T
UMENO, M
机构
关键词
D O I
10.1246/cl.1991.2073
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Palladium(II)-phosphine complexes, especially PdCl2(dppf) where dppf stands for 1,1'-bis(diphenylphosphino)ferrocene, are effective catalysts for the cross-coupling of Grignard reagents with dichlorobenzenes to produce selectively mono-alkylated and arylated benzenes. The addition of ligands is also effective for the cross-coupling of Grignard reagents containing a beta-hydrogen(s).
引用
收藏
页码:2073 / 2076
页数:4
相关论文
共 16 条
[1]   CHELATE-ASSISTED, PD-CATALYZED EFFICIENT CARBONYLATION OF ARYL CHLORIDES [J].
BENDAVID, Y ;
PORTNOY, M ;
MILSTEIN, D .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (23) :8742-8744
[2]   FORMYLATION OF ARYL CHLORIDES CATALYZED BY A PALLADIUM COMPLEX [J].
BENDAVID, Y ;
PORTNOY, M ;
MILSTEIN, D .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (23) :1816-1817
[3]   BIMETALLIC CATALYSIS - A NEW METHOD FOR THE ACTIVATION OF CHLOROARENES TOWARD PALLADIUM-CATALYZED COUPLING WITH OLEFINS [J].
BOZELL, JJ ;
VOGT, CE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (08) :2655-2657
[4]  
CORRIU RJP, 1972, J CHEM SOC CHEM COMM, P144
[5]   REGIOSPECIFIC SYNTHESIS OF AROMATIC-COMPOUNDS VIA ORGANOMETALLIC INTERMEDIATES .3. NORMAL-ALKYL-SUBSTITUTED BENZENE [J].
EAPEN, KC ;
DUA, SS ;
TAMBORSKI, C .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (03) :478-482
[6]   ADDITION OF ARYL HALIDES TO TETRAKIS(TRIPHENYLPHOSPHINE)PALLADIUM(0) [J].
FITTON, P ;
RICK, EA .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1971, 28 (02) :287-&
[7]   DICHLORO[1,1'-BIS(DIPHENYLPHOSPHINO)FERROCENE]PALLADIUM-(II) - AN EFFECTIVE CATALYST FOR CROSS-COUPLING OF SECONDARY AND PRIMARY ALKYL GRIGNARD AND ALKYLZINC REAGENTS WITH ORGANIC HALIDES [J].
HAYASHI, T ;
KONISHI, M ;
KOBORI, Y ;
KUMADA, M ;
HIGUCHI, T ;
HIROTSU, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (01) :158-163
[8]   SELECTIVE MONO-ALKYLATION AND ARYLATION OF AROMATIC DIHALIDES BY PALLADIUM-CATALYZED CROSS-COUPLING WITH THE GRIGNARD AND ORGANOZINC REAGENTS [J].
MINATO, A ;
TAMAO, K ;
HAYASHI, T ;
SUZUKI, K ;
KUMADA, M .
TETRAHEDRON LETTERS, 1980, 21 (09) :845-848
[9]   MECHANISTIC STUDIES OF NICKEL CATALYSIS IN CROSS COUPLING OF ARYL HALIDES WITH ALKYLMETALS - ROLE OF ARYLALKYLNICKEL(II) SPECIES AS INTERMEDIATES [J].
MORRELL, DG ;
KOCHI, JK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (25) :7262-7270
[10]   SIGMA-ARYL COMPOUNDS OF NICKEL, PALLADIUM, AND PLATINUM - SYNTHESIS AND BONDING STUDIES [J].
PARSHALL, GW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (08) :2360-2366