Development of a General Palladium-Catalyzed Carbonylative Heck Reaction of Aryl Halides

被引：210

作者：

Wu, Xiao-Feng ^{[1
]}

Neumann, Helfried ^{[1
]}

Spannenberg, Anke ^{[1
]}

Schulz, Thomas ^{[1
]}

Jiao, Haijun ^{[1
]}

Beller, Matthias ^{[1
]}

机构：

[1] Univ Rostock, Leibniz Inst Katalyse eV, D-18059 Rostock, Germany

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2010年 / 132卷 / 41期

关键词：

HETEROARYL BROMIDES; BOND FORMATION; CO-ETHYLENE; COMPLEXES; EFFICIENT; FORMYLATION; CYCLIZATION; ANTICANCER; INDANONES; ALDEHYDES;

D O I：

10.1021/ja1059922

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first general palladium-catalyzed carbonylative vinylation of aryl halides with olefins in the presence of CO has been developed. Applying a catalyst system consisting of [(cinnamyl)PdCl](2) and bulky imidazolylphosphine ligand L1 allows for the efficient and selective synthesis of alpha,beta-unsaturated ketones under mild reaction conditions. Starting from easily available aryl halides and olefins, versatile building blocks can be prepared in a straightforward manner. The generality and functional group tolerance of this novel protocol is demonstrated.

引用

页码：14596 / 14602

页数：7

共 101 条

[1] Structurally characterized intermediates in the stepwise insertion of CO-ethylene or CO-methyl acrylate into the metal-carbon bond of Pd(II) complexes stabilized by (phosphinomethyl)oxazoline ligands [J].

Agostinho, Magno ;

Braunstein, Pierre .

CHEMICAL COMMUNICATIONS, 2007, (01) :58-60

[2] Rate and mechanism of the heck reactions of arylpalladium complexes ligated by a bidentate P,P ligand with an electron-rich alkene (isobutyl vinyl ether) [J].

Amatore, Christian ;

Godin, Beatrice ;

Jutand, Anny ;

Lemaitre, Frederic .

ORGANOMETALLICS, 2007, 26 (07) :1757-1761

[3] Rate and mechanism of the reaction of alkenes with aryl palladium complexes ligated by a bidentate PP ligand in Heck reactions [J].

Amatore, Christian ;

Godin, Beatrice ;

Jutand, Anny ;

Lemaitre, Frederic .

CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (07) :2002-2011

[4]

Ambrosini L. M., 2010, SYNTHESIS-STUTTGART, V5, P870

[5] PALLADIUM-CATALYZED AROYLATION OF ALKYL VINYL ETHERS - AN ENTRY TO MONOPROTECTED 1-ARYL-1,3-DICARBONYL EQUIVALENTS [J].

ANDERSSON, CM ;

HALLBERG, A .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (18) :4257-4263

[6] ANTICANCER AND ANTIOXIDANT ACTIVITY OF SYNTHETIC CHALCONES AND RELATED-COMPOUNDS [J].

ANTO, RJ ;

SUKUMARAN, K ;

KUTTAN, G ;

RAO, MNA ;

SUBBARAJU, V ;

KUTTAN, R .

CANCER LETTERS, 1995, 97 (01) :33-37

[7] Rhodium catalyzed reaction of internal alkynes with organoborons under CO atmosphere: a product tunable reaction [J].

Artok, Levent ;

Kus, Melih ;

Aksin-Artok, Oezge ;

Dege, Fatma Nurcan ;

Oezkilinc, Fatma Yelda .

TETRAHEDRON, 2009, 65 (45) :9125-9133

[8] ASYMMETRIC-SYNTHESIS - ASYMMETRIC CATALYTIC ALLYLATION USING PALLADIUM CHIRAL PHOSPHINE COMPLEXES [J].

AUBURN, PR ;

MACKENZIE, PB ;

BOSNICH, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (07) :2033-2046

[9] Synthesis and biological evaluation of simple methoxylated chalcones as anticancer, anti-inflammatory and antioxidant agents [J].

Bandgar, Babasaheb P. ;

Gawande, Shrikant S. ;

Bodade, Ragini G. ;

Totre, Jalinder V. ;

Khobragade, Chandrahas N. .

BIOORGANIC & MEDICINAL CHEMISTRY, 2010, 18 (03) :1364-1370

[10] Palladium-Catalyzed Carbonylation-A Reaction Come of Age [J].

Barnard, Christopher F. J. .

ORGANOMETALLICS, 2008, 27 (21) :5402-5422

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