Aryl to aryl palladium migration in the Heck and Suzuki coupling of o-halobiaryls

被引：99

作者：

Campo, Marino A. ^{[1
]}

Zhang, Haiming ^{[1
]}

Yao, Tuanli ^{[1
]}

Ibdah, Abdellatif ^{[1
]}

McCulla, Ryan D. ^{[1
]}

Huang, Qinhua ^{[1
]}

Zhao, Jian ^{[1
]}

Jenks, William S. ^{[1
]}

Larock, Richard C. ^{[1
]}

机构：

[1] Iowa State Univ, Dept Chem, Ames, IA 50011 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2007年 / 129卷 / 19期

关键词：

D O I：

10.1021/ja069238z

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A novel 1,4-palladium migration between the o- and o'-positions of biaryls has been observed in organopalladium intermediates derived from o-halobiaryls. The organopalladium intermediates generated by this migration have been trapped either by a Heck reaction employing ethyl acrylate or by Suzuki cross-coupling using arylboronic acids. This palladium migration can be activated or deactivated by choosing the appropriate reaction conditions. Chemical and computational evidence supports the presence of an equilibrium that correlates with the C-H acidity of the available arene positions.

引用

页码：6298 / 6307

页数：10

共 51 条

[1] DENSITY-FUNCTIONAL THERMOCHEMISTRY .3. THE ROLE OF EXACT EXCHANGE
BECKE, AD
[J]. JOURNAL OF CHEMICAL PHYSICS, 1993, 98 (07) : 5648 - 5652
[2] DENSITY-FUNCTIONAL EXCHANGE-ENERGY APPROXIMATION WITH CORRECT ASYMPTOTIC-BEHAVIOR
BECKE, AD
[J]. PHYSICAL REVIEW A, 1988, 38 (06): : 3098 - 3100
[3] MacMolPlt: A graphical user interface for GAMESS
Bode, BM
Gordon, MS
[J]. JOURNAL OF MOLECULAR GRAPHICS & MODELLING, 1998, 16 (03) : 133 - +
[4] RECENT DEVELOPMENTS AND NEW PERSPECTIVES IN THE HECK REACTION
CABRI, W
CANDIANI, I
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1995, 28 (01) : 2 - 7
[5] Catalytic direct arylation with aryl chlorides, bromides, and iodides: Intramolecular studies leading to new intermolecular reactions
Campeau, LC
Parisien, M
Jean, A
Fagnou, K
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (02) : 581 - 590
[6] Palladium-catalyzed direct arylation of simple arenes in synthesis of biaryl molecules
Campeau, LC
Fagnou, K
[J]. CHEMICAL COMMUNICATIONS, 2006, (12) : 1253 - 1264
[7] Biaryl synthesis via direct arylation: Establishment of an efficient catalyst for intramolecular processes
Campeau, LC
Parisien, M
Leblanc, M
Fagnou, K
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (30) : 9186 - 9187
[8] Novel 1,4-palladium migration in organopalladium intermediates derived from o-iodobiaryis
Campo, MA
Larock, RC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (48) : 14326 - 14327
[9] DEVELOPMENT OF ORGANOPALLADIUM(IV) CHEMISTRY - FUNDAMENTAL-ASPECTS AND SYSTEMS FOR STUDIES OF MECHANISM IN ORGANOMETALLIC CHEMISTRY AND CATALYSIS
CANTY, AJ
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1992, 25 (02) : 83 - 90
[10] MECHANISMS OF D(8) ORGANOMETALLIC REACTIONS INVOLVING ELECTROPHILES AND INTRAMOLECULAR ASSISTANCE BY NUCLEOPHILES
CANTY, AJ
VANKOTEN, G
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1995, 28 (10) : 406 - 413

← 1 2 3 4 5 6 →