Pd-Catalyzed Intramolecular Acylation of Aryl Bromides via C-H Functionalization: A Highly Efficient Synthesis of Benzocyclobutenones

被引：117

作者：

Alvarez-Bercedo, Paula ^{[1
]}

Flores-Gaspar, Areli ^{[1
]}

Correa, Arkaitz ^{[1
]}

Martin, Ruben ^{[1
]}

机构：

[1] Inst Chem Res Catalonia ICIQ, Tarragona 43007, Spain

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2010年 / 132卷 / 02期

关键词：

KETENE SILYL ACETAL; RING EXPANSION; PALLADIUM CATALYSIS; AROMATIC-ALDEHYDES; KETONES; DERIVATIVES; ANNULATION; COMPLEXES; INSERTION; BENZYNE;

D O I：

10.1021/ja909811t

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A new catalyst system for the intramolecular acylation of aldehydes with aryl bromides via C-H functionalization is described. The transformation is distinguished by a remarkable functional group tolerance and hence allows for the synthesis of a wide variety of highly functionalized benzocyclobutenones with a diverse set of substitution patterns from simple and easily accessible precursors.

引用

页码：466 / +

页数：3

共 36 条

[1] A NOVEL SYNTHESIS OF BENZOCYCLOBUTENONES [J].

AIDHEN, IS ;

AHUJA, JR .

TETRAHEDRON LETTERS, 1992, 33 (37) :5431-5432

[2] The heck reaction as a sharpening stone of palladium catalysis [J].

Beletskaya, IP ;

Cheprakov, AV .

CHEMICAL REVIEWS, 2000, 100 (08) :3009-3066

[3] CYCLOBUTANONES AND CYCLOBUTENONES IN NATURE AND IN SYNTHESIS [J].

BELLUS, D ;

ERNST, B .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1988, 27 (06) :797-827

[4] Arene chromium complexes with functionalized anellated rings.: Selective formation of highly substituted polycycles [J].

Butenschön, H .

PURE AND APPLIED CHEMISTRY, 2002, 74 (01) :57-62

[5] Palladium-catalyzed reaction of aryl iodides with acetic anhydride. A carbon monoxide-free synthesis of acetophenones [J].

Cacchi, S ;

Fabrizi, G ;

Gavazza, F ;

Goggiamani, A .

ORGANIC LETTERS, 2003, 5 (03) :289-291

[6] Synthesis of Benzocyclobutenes by Palladium-Catalyzed C-H Activation of Methyl Groups: Method and Mechanistic Study [J].

Chaumontet, Manon ;

Piccardi, Riccardo ;

Audic, Nicolas ;

Hitce, Julien ;

Peglion, Jean-Louis ;

Clot, Eric ;

Baudoin, Olivier .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (45) :15157-15166

[7] Palladium-Catalyzed Direct Carboxylation of Aryl Bromides with Carbon Dioxide [J].

Correa, Arkaitz ;

Martin, Ruben .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (44) :15974-+

[8] Synthesis of indenols and indanones via catalytic cyclic vinylpalladation of aromatic aldehydes [J].

Gevorgyan, V ;

Quan, LG ;

Yamamoto, Y .

TETRAHEDRON LETTERS, 1999, 40 (21) :4089-4092

[9] Poly-oxygenated tricyclobutabenzenes via repeated [2+2] cycloaddition of benzyne and ketene silyl acetal [J].

Hamura, T ;

Ibusuki, Y ;

Uekusa, H ;

Matsumoto, T ;

Suzuki, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (11) :3534-3535

[10] Strain-induced regioselectivities in reactions of benzyne possessing a fused four-membered ring [J].

Hamura, T ;

Ibusuki, Y ;

Sato, K ;

Matsumoto, T ;

Osamura, Y ;

Suzuki, K .

ORGANIC LETTERS, 2003, 5 (20) :3551-3554

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