Ruthenium- and rhodium-catalyzed oxidative alkylation of C-H bonds: efficient access to β-aryl ketones

被引：45

作者：

Qi, Ji ^{[1
]}

Huang, Liangbin ^{[2
]}

Wang, Zhaoyang ^{[1
]}

Jiang, Huanfeng ^{[2
]}

机构：

[1] S China Normal Univ, Sch Chem & Environm, Guangzhou 510006, Guangdong, Peoples R China

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

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2013年 / 11卷 / 46期

基金：

国家教育部博士点专项基金资助; 中国国家自然科学基金;

关键词：

ACTIVATION; FUNCTIONALIZATION; CARBONYLATION; (HETERO)ARENES; OLEFINATION; CYCLIZATION; PYRIDINES; ARYLATION; INSERTION; AMIDES;

D O I：

10.1039/c3ob41590b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Ruthenium- and rhodium-catalyzed oxidative couplings between versatile directed aromatic C-H bonds and allylic alcohols have been achieved. This method provides efficient synthesis of functional beta-aryl ketones and aldehydes in good to excellent yields, and the carbonyl group in the desired products was a significant synthon for organic synthesis.

引用

页码：8009 / 8013

页数：5

共 53 条

[1] Transition-Metal-Catalyzed Direct Arylation of (Hetero)Arenes by C-H Bond Cleavage [J].

Ackermann, Lutz ;

Vicente, Ruben ;

Kapdi, Anant R. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (52) :9792-9826

[2]

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

[3] Rh-Catalyzed Intermolecular Carbenoid Functionalization of Aromatic C-H Bonds by α-Diazomalonates [J].

Chan, Wai-Wing ;

Lo, Siu-Fung ;

Zhou, Zhongyuan ;

Yu, Wing-Yiu .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (33) :13565-13568

[4] C-H Activation: A Complementary Tool in the Total Synthesis of Complex Natural Products [J].

Chen, David Y. -K. ;

Youn, So Won .

CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (31) :9452-9474

[5] Palladium(II)-Catalyzed C-H Activation/C-C Cross-Coupling Reactions: Versatility and Practicality [J].

Chen, Xiao ;

Engle, Keary M. ;

Wang, Dong-Hui ;

Yu, Jin-Quan .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (28) :5094-5115

[6] Recent advances in the transition metal-catalyzed twofold oxidative C-H bond activation strategy for C-C and C-N bond formation [J].

Cho, Seung Hwan ;

Kim, Ji Young ;

Kwak, Jaesung ;

Chang, Sukbok .

CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) :5068-5083

[7] 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

[8] Pd(II)-Catalyzed ortho- or meta-C-H Olefination of Phenol Derivatives [J].

Dai, Hui-Xiong ;

Li, Gang ;

Zhang, Xing-Guo ;

Stepan, Antonia F. ;

Yu, Jin-Quan .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (20) :7567-7571

[9] Synthesis of 1,2-and 1,3-Dicarboxylic Acids via Pd(II)-Catalyzed Carboxylation of Aryl and Vinyl C-H Bonds [J].

Giri, Ramesh ;

Yu, Jin-Quan .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (43) :14082-+

[10] Rhodium-Catalyzed Direct Oxidative Carbonylation of Aromatic C-H Bond with CO and Alcohols [J].

Guan, Zheng-Hui ;

Ren, Zhi-Hui ;

Spinella, Stephen M. ;

Yu, Shichao ;

Liang, Yong-Min ;

Zhang, Xumu .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (02) :729-733

← 1 2 3 4 5 6 →