Theoretical aspects of palladium-catalysed carbon-carbon cross-coupling reactions

被引：336

作者：

Xue, Liqin ^{[1
]}

Lin, Zhenyang ^{[1
]}

机构：

[1] Hong Kong Univ Sci & Technol, Dept Chem, Kowloon, Hong Kong, Peoples R China

来源：

CHEMICAL SOCIETY REVIEWS | 2010年 / 39卷 / 05期

关键词：

DENSITY-FUNCTIONAL THEORY; N-HETEROCYCLIC CARBENE; OXIDATIVE ADDITION; SUZUKI-MIYAURA; REDUCTIVE ELIMINATION; STILLE REACTION; ARYL CHLORIDES; HECK REACTION; C-H; TRANSMETALATION STEP;

D O I：

10.1039/b814973a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Palladium-catalysed processes for the formation of carbon-carbon bonds, i.e., coupling reactions of organic halides ((RX)-X-1) and main-group organometallic compounds ((RM)-M-2) are most frequently applied in synthesizing biologically and pharmaceutically important organic molecules. In this article, we provide a critical review on theoretical studies of the palladium-catalysed carbon-carbon cross-coupling reactions, and give an up-to-date summary of the current understanding of the cross-coupling reactions from a theoretical point of view (108 references).

引用

页码：1692 / 1705

页数：14

共 114 条

[21] Computational characterization of the role of the base in the Suzuki-Miyaura cross-coupling reaction [J].

Braga, AAC ;

Morgon, NH ;

Ujaque, G ;

Maseras, F .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (25) :9298-9307

[22] Computational study of the transmetalation process in the Suzuki-Miyaura cross-coupling of aryls [J].

Braga, Ataualpa A. C. ;

Morgon, Nelson H. ;

Ujaque, Gregori ;

Lledos, Agusti ;

Maseras, Feliu .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2006, 691 (21) :4459-4466

[23] A DFT study of the full catalytic cycle of the Suzuki-Miyaura cross-coupling on a model system [J].

Braga, Ataualpa A. C. ;

Ujaque, Gregori ;

Maseras, Feliu .

ORGANOMETALLICS, 2006, 25 (15) :3647-3658

[24] RECENT DEVELOPMENTS AND NEW PERSPECTIVES IN THE HECK REACTION [J].

CABRI, W ;

CANDIANI, I .

ACCOUNTS OF CHEMICAL RESEARCH, 1995, 28 (01) :2-7

[25] DEVELOPMENT OF ORGANOPALLADIUM(IV) CHEMISTRY - FUNDAMENTAL-ASPECTS AND SYSTEMS FOR STUDIES OF MECHANISM IN ORGANOMETALLIC CHEMISTRY AND CATALYSIS [J].

CANTY, AJ .

ACCOUNTS OF CHEMICAL RESEARCH, 1992, 25 (02) :83-90

[26] On the configuration resulting from oxidative addition of RX to Pd(PPh3)4 and the mechanism of the cis-to-trans isomerization of [PdRX(PPh3)2] complexes (R equals aryl, X equals halide) [J].

Casado, AL ;

Espinet, P .

ORGANOMETALLICS, 1998, 17 (05) :954-959

[27] Mechanism of the Stille reaction.: 1.: The transmetalation step.: Coupling of R1I and R2SnBu3 catalyzed by trans-[PdR1IL2] (R1 = C6Cl2F3; R2 = vinyl, 4-methoxyphenyl; L = AsPh3) [J].

Casado, AL ;

Espinet, P .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (35) :8978-8985

[28] Mechanism of the stille reaction. 2. Couplings of aryl triflates with vinyltributyltin. Observation of intermediates. A more comprehensive scheme [J].

Casado, AL ;

Espinet, P ;

Gallego, AM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (48) :11771-11782

[29]

Casares JA, 2002, CHEM-EUR J, V8, P4843, DOI 10.1002/1521-3765(20021104)8:21<4843::AID-CHEM4843>3.0.CO

[30]

2-I

← 1 2 3 4 5 6 7 8 9 10 →