Structural and mechanistic studies of Pd-catalyzed C-C bond formation:: The case of carbonylation and Heck reaction

被引:185
作者
Trzeciak, AM [1 ]
Ziólkowski, JJ [1 ]
机构
[1] Univ Wroclaw, Fac Chem, PL-50383 Wroclaw, Poland
关键词
palladium complexes; Palladium(0) colloid; C-C coupling; heck reaction; carbonylation reaction;
D O I
10.1016/j.ccr.2005.02.001
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The extraordinary catalytic activity of palladium in C-C bond forming processes is reviewed in respect to Heck and carbonylation reactions. Examples of catalytic systems based on palladium complexes with phosphorus ligands and phosphine-free systems and based on the Pd(0) colloid are presented. The two key steps of both reaction mechanisms: first, reduction of Pd(II) to Pd(0) complexes or Pd(0) colloids and second, oxidative addition of substrates (aryl or benzyl halides) are discussed. (c) 2005 Elsevier B.V. All rights reserved.
引用
收藏
页码:2308 / 2322
页数:15
相关论文
共 111 条
[1]   RATES AND MECHANISM OF THE FORMATION OF ZEROVALENT PALLADIUM COMPLEXES FROM MIXTURES OF PD(OAC)(2) AND TERTIARY PHOSPHINES AND THEIR REACTIVITY IN OXIDATIVE ADDITIONS [J].
AMATORE, C ;
CARRE, E ;
JUTAND, A ;
MBARKI, MA .
ORGANOMETALLICS, 1995, 14 (04) :1818-1826
[2]   Mechanistic and kinetic studies of palladium catalytic systems [J].
Amatore, C ;
Jutand, A .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1999, 576 (1-2) :254-278
[4]   Phenyl backbone-derived P,O- and P,N-ligands for palladium/ligand-catalyzed aminations of aryl bromides, iodides, and chlorides.: Syntheses and structures of (P,O)n-palladium(II)aryl(Br) complexes [J].
Bei, XH ;
Uno, T ;
Norris, J ;
Turner, HW ;
Weinberg, WH ;
Guram, AS ;
Petersen, JL .
ORGANOMETALLICS, 1999, 18 (10) :1840-1853
[5]   The heck reaction as a sharpening stone of palladium catalysis [J].
Beletskaya, IP ;
Cheprakov, AV .
CHEMICAL REVIEWS, 2000, 100 (08) :3009-3066
[6]   Catalytic Markovnikov and anti-Markovnikov functionalization of alkenes and alkynes: Recent developments and trends [J].
Beller, M ;
Seayad, J ;
Tillack, A ;
Jiao, H .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (26) :3368-3398
[7]  
Beller M, 2001, CHIMIA, V55, P684
[8]   PROGRESS IN HYDROFORMYLATION AND CARBONYLATION [J].
BELLER, M ;
CORNILS, B ;
FROHNING, CD ;
KOHLPAINTNER, CW .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1995, 104 (01) :17-85
[9]   First palladium-catalyzed Heck reactions with efficient colloidal catalyst systems [J].
Beller, M ;
Fischer, H ;
Kuhlein, K ;
Reisinger, CP ;
Herrmann, WA .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1996, 520 (1-2) :257-259
[10]   Palladium catalyzed hydroxycarbonylation of olefins in biphasic system: beneficial effect of alkali metal salt and protective-colloid agents on the stability of the catalytic system [J].
Bertoux, F ;
Monflier, E ;
Castanet, Y ;
Mortreux, A .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1999, 143 (1-3) :23-30