Catalytic Pauson Khand and related cycloaddition reactions

被引：43

作者：

Hanson, BE ^{[1
]}

机构：

[1] Virginia Tech, Dept Chem, Blacksburg, VA 24061 USA

来源：

COMMENTS ON INORGANIC CHEMISTRY | 2002年 / 23卷 / 04期

关键词：

catalysis; Pauson Khand reaction; cycloaddition reactions; cobalt; ruthenium; rhodium; iridium;

D O I：

10.1080/02603590213137

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The Pauson Khand reaction is a powerful synthetic tool that yields cyclopentenones by the 2+2+1 cycloaddition of an alkyne, an alkene, and carbon monoxide. The reaction is widely practiced stoichiometrically and requires an equivalent of dicobalt octacarbonyl to effect the cycloaddition. Recent advances in the development of catalysts have extended the application of the reaction. Catalysts include complexes of cobalt, rhodium, iridium, ruthenium, and titanium. With ruthenium catalysts it has been discovered that unsaturated substrates containing heteroatoms, such as imines and aldehydes, can be used in 2+2+1 cycloadditions. Catalysts and proposed mechanisms for the Pauson Khand reaction are reviewed here.

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收藏

页码：289 / 318

页数：30

相关论文

共 110 条

[11] The molybdenum-mediated tandem Pauson-Khand reaction. High yield entry into [5.5.5.5]tetracyclic systems [J].

Cao, H ;

Van Ornum, SG ;

Cook, JM .

TETRAHEDRON LETTERS, 2000, 41 (28) :5313-5316

[12] The first alkyne-dicobaltcarbonyl complex with a bidentate chiral ligand with Co-P and Co-N coordination [J].

Castro, J ;

Moyano, A ;

Pericàs, MA ;

Riera, A ;

Alvarez-Larena, A ;

Piniella, JF .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1999, 585 (01) :53-58

[13] Acetylene-dicobaltcarbonyl complexes with chiral phosphinooxazoline ligands:: Synthesis, structural characterization, and application to enantioselective intermolecular Pauson-Khand reactions [J].

Castro, J ;

Moyano, A ;

Pericàs, MA ;

Riera, A ;

Alvarez-Larena, A ;

Piniella, JF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (33) :7944-7952

[14] Ru3(CO)12-catalyzed cyclocarbonylation of yne-aldehydes to bicyclic α,β-unsaturated γ-butyrolactones [J].

Chatani, N ;

Morimoto, T ;

Fukumoto, Y ;

Murai, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (21) :5335-5336

[15] Ruthenium carbonyl-catalyzed [2+2+1]-cycloaddition of ketones, olefins, and carbon monoxide, leading to functionalized γ-butyrolactones [J].

Chatani, N ;

Tobisu, M ;

Asaumi, T ;

Fukumoto, Y ;

Murai, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (30) :7160-7161

[16] Ru3(CO)12-catalyzed reaction of yne-imines with carbon monoxide leading to bicyclic α,β-unsaturated lactams [J].

Chatani, N ;

Morimoto, T ;

Kamitani, A ;

Fukumoto, Y ;

Murai, S .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1999, 579 (1-2) :177-181

[17]

Chung YK, 1999, COORDIN CHEM REV, V188, P297

[18] Polymer-supported cobalt carbonyl complexes as novel solid-phase catalysts of the Pauson-Khand reaction [J].

Comely, AC ;

Gibson, SE ;

Hales, NJ .

CHEMICAL COMMUNICATIONS, 2000, (04) :305-306

[19] New stable catalysts of the Pauson-Khand annelation [J].

Comely, AC ;

Gibson, SE ;

Stevenazzi, A ;

Hales, NJ .

TETRAHEDRON LETTERS, 2001, 42 (06) :1183-1185

[20] Synthesis and reactivity of Ir(CO)(eta(2)-C2R2)(eta(5)-C9H7) (R=Ph, Tol). Alkyne coupling and arene C-H bond activation forming a substituted butadiene ligand [J].

Comstock, MC ;

Shapley, JR .

ORGANOMETALLICS, 1997, 16 (22) :4816-4823

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