Direct arylation reactions catalyzed by Pd(OH)2/C:: Evidence for a soluble palladium catalyst

被引：293

作者：

Parisien, M ^{[1
]}

Valette, D ^{[1
]}

Fagnou, K ^{[1
]}

机构：

[1] Univ Ottawa, Ctr Catalysis Res & Innovat, Dept Chem, Ottawa, ON K1N 6N5, Canada

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 19期

关键词：

D O I：

10.1021/jo051039v

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Palladium hydroxide on carbon (Pearlman's catalyst) effectively catalyzes direct arylation reactions of aryl iodides and bromides, providing excellent arylation-to-hydrodehalogenation ratios (> 30:1) with broad scope for both intra- and intermolecular arylation processes. Studies aimed at determining the nature of the active catalyst indicate that an active homogeneous palladium species is produced under the reaction conditions.

引用

页码：7578 / 7584

页数：7

共 51 条

[1] PALLADIUM-CATALYZED CYCLIZATION OF 2-SUBSTITUTED HALOGENOARENES BY DEHYDROHALOGENATION [J].

AMES, DE ;

OPALKO, A .

TETRAHEDRON, 1984, 40 (10) :1919-1925

[2] Heterogeneous or homogeneous? A case study involving palladium-containing perovskites in the Suzuki reaction [J].

Andrews, SP ;

Stepan, AF ;

Tanaka, H ;

Ley, SV ;

Smith, MD .

ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (05) :647-654

[3] HETEROGENEOUS CATALYSIS IN ORGANIC-CHEMISTRY .8. THE USE OF SUPPORTED PALLADIUM CATALYSTS FOR THE HECK ARYLATION [J].

AUGUSTINE, RL ;

OLEARY, ST .

JOURNAL OF MOLECULAR CATALYSIS, 1992, 72 (02) :229-242

[4] GENERAL-APPROACH TO HIGHLY FUNCTIONALIZED BENZYLIC ORGANOMETALLICS OF ZINC AND COPPER [J].

BERK, SC ;

KNOCHEL, P ;

YEH, MCP .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (24) :5789-5791

[5] Catalyst product separation techniques in Heck reaction [J].

Bhanage, BM ;

Arai, M .

CATALYSIS REVIEWS-SCIENCE AND ENGINEERING, 2001, 43 (03) :315-344

[6] Multistep synthesis of 2,5-diketopiperazines on different solid supports monitored by high resolution magic angle spinning NMR spectroscopy [J].

Bianco, A ;

Furrer, J ;

Limal, D ;

Guichard, G ;

Elbayed, K ;

Raya, J ;

Piotto, M ;

Briand, JP .

JOURNAL OF COMBINATORIAL CHEMISTRY, 2000, 2 (06) :681-690

[7] Bu3SnH mediated oxidative radical cyclisations:: synthesis of 6H-benzo[c]chromen-6-ones [J].

Bowman, WR ;

Mann, E ;

Parr, J .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (17) :2991-2999

[8] High-yielding intramolecular direct arylation reactions with aryl chlorides [J].

Campeau, LC ;

Thansandote, P ;

Fagnou, K .

ORGANIC LETTERS, 2005, 7 (09) :1857-1860

[9] Biaryl synthesis via direct arylation: Establishment of an efficient catalyst for intramolecular processes [J].

Campeau, LC ;

Parisien, M ;

Leblanc, M ;

Fagnou, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (30) :9186-9187

[10] 1,4-Palladium migration via C-H activation, followed by arylation: Synthesis of fused polycycles [J].

Campo, MA ;

Huang, QH ;

Yao, TL ;

Tian, QP ;

Larock, RC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (38) :11506-11507

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