The mechanism of the oxidative addition of aryl halides to Pd-catalysts: a DFT investigation

被引：109

作者：

Goossen, LJ ^{[1
]}

Koley, D ^{[1
]}

Hermann, H ^{[1
]}

Thiel, W ^{[1
]}

机构：

[1] Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany

来源：

CHEMICAL COMMUNICATIONS | 2004年 / 19期

关键词：

D O I：

10.1039/b409144b

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Based on DFT calculations, a new mechanism for the oxidative addition of aryl halides to Pd-catalysts is presented. The key intermediate is an anionic Pd-species in which the aryl halide coordinates to the palladium via the halide atom.

引用

页码：2141 / 2143

页数：3

共 42 条

[1] ELECTRONIC-STRUCTURE CALCULATIONS ON WORKSTATION COMPUTERS - THE PROGRAM SYSTEM TURBOMOLE [J].

AHLRICHS, R ;

BAR, M ;

HASER, M ;

HORN, H ;

KOLMEL, C .

CHEMICAL PHYSICS LETTERS, 1989, 162 (03) :165-169

[2] On C-C coupling by carbene-stabilized palladium catalysts: A density functional study of the Heck reaction [J].

Albert, K ;

Gisdakis, P ;

Rosch, N .

ORGANOMETALLICS, 1998, 17 (08) :1608-1616

[3] INTIMATE MECHANISM OF OXIDATIVE ADDITION TO ZEROVALENT PALLADIUM COMPLEXES IN THE PRESENCE OF HALIDE-IONS AND ITS RELEVANCE TO THE MECHANISM OF PALLADIUM-CATALYZED NUCLEOPHILIC SUBSTITUTIONS [J].

AMATORE, C ;

JUTAND, A ;

SUAREZ, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (21) :9531-9541

[4] Anionic Pd(0) and Pd(II) intermediates in palladium-catalyzed Heck and cross-coupling reactions [J].

Amatore, C ;

Jutand, A .

ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (05) :314-321

[5] RATES AND MECHANISM OF THE REVERSIBLE OXIDATIVE ADDITION OF (Z)-1,2-DICHLOROETHYLENE AND (E)-1,2-DICHLOROETHYLENE TO LOW-LIGATED ZERO-VALENT PALLADIUM [J].

AMATORE, C ;

AZZABI, M ;

JUTAND, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (05) :1670-1677

[6] ENERGY-ADJUSTED ABINITIO PSEUDOPOTENTIALS FOR THE 2ND AND 3RD ROW TRANSITION-ELEMENTS [J].

ANDRAE, D ;

HAUSSERMANN, U ;

DOLG, M ;

STOLL, H ;

PREUSS, H .

THEORETICA CHIMICA ACTA, 1990, 77 (02) :123-141

[7] Quantum calculation of molecular energies and energy gradients in solution by a conductor solvent model [J].

Barone, V ;

Cossi, M .

JOURNAL OF PHYSICAL CHEMISTRY A, 1998, 102 (11) :1995-2001

[8] DENSITY-FUNCTIONAL EXCHANGE-ENERGY APPROXIMATION WITH CORRECT ASYMPTOTIC-BEHAVIOR [J].

BECKE, AD .

PHYSICAL REVIEW A, 1988, 38 (06) :3098-3100

[9] AB-INITIO ENERGY-ADJUSTED PSEUDOPOTENTIALS FOR ELEMENTS OF GROUPS 13-17 [J].

BERGNER, A ;

DOLG, M ;

KUCHLE, W ;

STOLL, H ;

PREUSS, H .

MOLECULAR PHYSICS, 1993, 80 (06) :1431-1441

[10] OXIDATIVE INSERTION AS FRONTSIDE S(N)2 SUBSTITUTION - A THEORETICAL-STUDY OF THE MODEL REACTION SYSTEM PD+CH3CL [J].

BICKELHAUPT, FM ;

ZIEGLER, T ;

SCHLEYER, PV .

ORGANOMETALLICS, 1995, 14 (05) :2288-2296

← 1 2 3 4 5 →