Rh(III)-catalyzed ortho-oxidative alkylation of unactivated arenes with allylic alcohols

被引：98

作者：

Huang, Liangbin ^{[1
]}

Wang, Qian ^{[1
]}

Qi, Ji ^{[1
]}

Wu, Xia ^{[1
]}

Huang, Kefan ^{[1
]}

Jiang, Huanfeng ^{[1
]}

机构：

[1] S China Univ Technol, Sch Chem & Chem Engn, Guangzhou 510640, Guangdong, Peoples R China

来源：

CHEMICAL SCIENCE | 2013年 / 4卷 / 06期

基金：

中国国家自然科学基金; 国家教育部博士点专项基金资助;

关键词：

H BOND ACTIVATION; CROSS-COUPLING REACTION; HECK REACTION; C-C; PD(II)-CATALYZED OLEFINATION; PALLADIUM CATALYST; AROMATIC IMINES; BENZOIC-ACIDS; ALKENES; EFFICIENT;

D O I：

10.1039/c3sc50630d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Versatile directed aromatic C-H bond activation and oxidative coupling with allylic alcohols is reported using a cationic Rh(III) catalyst. This method provides efficient and robust synthesis of functional beta-aryl ketones and indolines in good yields with excellent regioselectivity, even the reaction runs at 3 g scale. The catalytic systems have good functional group tolerance, such as CONR2, NHAc, NO2, CF3, CN, Cl, Br and I.

引用

页码：2665 / 2669

页数：5

共 68 条

[1] Ruthenium-Catalyzed Oxidative C-H Alkenylations of Anilides and Benzamides in Water [J].

Ackermann, Lutz ;

Wang, Lianhui ;

Wolfram, Ratnakancana ;

Lygin, Alexander V. .

ORGANIC LETTERS, 2012, 14 (03) :728-731

[2] Ruthenium-Catalyzed Oxidative C-H Bond Alkenylations in Water: Expedient Synthesis of Annulated Lactones [J].

Ackermann, Lutz ;

Pospech, Jola .

ORGANIC LETTERS, 2011, 13 (16) :4153-4155

[3] Carboxylate-Assisted Transition-Metal-Catalyzed C-H Bond Functionalizations: Mechanism and Scope [J].

Ackermann, Lutz .

CHEMICAL REVIEWS, 2011, 111 (03) :1315-1345

[4] Ruthenium-Catalyzed Regioselective Direct Alkylation of Arenes with Unactivated Alkyl Halides through C-H Bond Cleavage [J].

Ackermann, Lutz ;

Novak, Petr ;

Vicente, Ruben ;

Hofmann, Nora .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (33) :6045-6048

[5] Ruthenium diacetate-catalysed oxidative alkenylation of C-H bonds in air: synthesis of alkenyl N-arylpyrazoles [J].

Arockiam, Percia B. ;

Fischmeister, Cedric ;

Bruneau, Christian ;

Dixneuf, Pierre H. .

GREEN CHEMISTRY, 2011, 13 (11) :3075-3078

[6]

Arockiam PB, 2012, CHEM REV, V112, P5879, DOI [10.1021/cr300153J, 10.1021/cr300153j]

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

Beletskaya, IP ;

Cheprakov, AV .

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

[8] Selective Pd-catalyzed oxidative coupling of anilides with olefins through C-H bond activation at room temperature [J].

Boele, MDK ;

van Strijdonck, GPF ;

de Vries, AHM ;

Kamer, PCJ ;

de Vries, JG ;

van Leeuwen, PWNM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (08) :1586-1587

[9] Rhodium Catalyzed Chelation-Assisted C-H Bond Functionalization Reactions [J].

Colby, Denise A. ;

Tsai, Andy S. ;

Bergman, Robert G. ;

Ellman, Jonathan A. .

ACCOUNTS OF CHEMICAL RESEARCH, 2012, 45 (06) :814-825

[10] Rhodium-Catalyzed C-C Bond Formation via Heteroatom-Directed C-H Bond Activation [J].

Colby, Denise A. ;

Bergman, Robert G. ;

Ellman, Jonathan A. .

CHEMICAL REVIEWS, 2010, 110 (02) :624-655

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