ELECTROCATALYTIC COUPLING OF ARYL HALIDES WITH (1,2-BIS(DI-2-PROPYLPHOSPHINO)BENZENE)NICKEL(0)

被引:35
作者
FOX, MA
CHANDLER, DA
LEE, CJ
机构
[1] Department of Chemistry, University of Texas at Austin, Austin
关键词
D O I
10.1021/jo00010a014
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Dibromo- and dichloro(1,2-bis(di-2-propylphosphino)benzene)nickel(II) is compared with tetrakis(triphenylphosphino)nickel(II) as an electrocatalyst for the reductive coupling of aryl halides. In many of the reactions examined, dehalogenation of the substrate predominated over coupling; however, preparative yields of biphenyls as high as 96% can be obtained with aryl chlorides and 2 mol % of the title catalyst in polar, coordinating solvents. Experimental factors governing the efficiency of these reactions are discussed, and possible mechanisms for coupling and catalyst deactivation are considered. Much better selectivity for aryl chlorides is attained in electroreductive couplings catalyzed by the title compound, whereas electrocatalysis with (Ph3P)4NiCl2 allows for selective intra- and intermolecular coupling at aryl bromide and vinyl chloride sites. Modest yields of cyclization products can be attained with either electrocatalyst in the presence of appropriately functionalized aryl or vinyl halides.
引用
收藏
页码:3246 / 3255
页数:10
相关论文
共 40 条
[1]   RATES AND MECHANISM OF BIPHENYL SYNTHESIS CATALYZED BY ELECTROGENERATED COORDINATIVELY UNSATURATED NICKEL-COMPLEXES [J].
AMATORE, C ;
JUTAND, A .
ORGANOMETALLICS, 1988, 7 (10) :2203-2214
[2]   N-(ORTHO-BROMOPHENYL)-ORTHO-BROMOBENZYLAMINE [J].
BERNDT, AF ;
SCHLEMPER, EO .
ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE, 1982, 38 (SEP) :2493-2496
[3]  
BONTEMPELLI G, 1981, J CHEM SOC DA, P1074
[4]  
CAREY FA, 1983, ADV ORGANIC CHEM B, P281
[5]  
CHANDLER DA, IN PRESS J COORD CHE
[6]   COUPLING OF ARYL CHLORIDES BY NICKEL AND REDUCING METALS [J].
COLON, I ;
KELSEY, DR .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (14) :2627-2637
[7]   UNSYMMETRICAL BIPHENYL SYNTHESIS USING COPPER(I) TERT-BUTOXIDE [J].
CORNFORTH, J ;
SIERAKOWSKI, AF ;
WALLACE, TW .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1979, (06) :294-295
[8]  
DEVRIES VG, 1983, Patent No. 324781
[9]   KRISTALLSTRUKTUR DES BENZOL-ADDUKTS DES 1,2,3,4-TETRAMETHYLCYCLOBUTADIEN-NICKEL(II)-CHLORIDS, (C8H12,NICL2)2,C6H6 [J].
DUNITZ, JD ;
SHEARER, HMM ;
MEZ, HC ;
MILLS, OS .
HELVETICA CHIMICA ACTA, 1962, 45 (02) :647-&
[10]  
EARLEY RA, 1970, J CHEM SOC, P151