Palladium-catalyzed C(carbonyl)-C bond cleavage of amides: a facile access to phenylcarbamate derivatives with alcohols

被引：13

作者：

Yan, Xufei ^{[1
]}

Sun, Huihui ^{[1
]}

Xiang, Haifeng ^{[1
]}

Yu, Da-Gang ^{[1
]}

Luo, Daibing ^{[2
]}

Zhou, Xiangge ^{[1
]}

机构：

[1] Sichuan Univ, Coll Chem, 29 Wangjiang Rd, Chengdu 610064, Sichuan, Peoples R China

[2] Sichuan Univ, Analyt & Testing Ctr, 29 Wangjiang Rd, Chengdu 610064, Sichuan, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2018年 / 54卷 / 62期

基金：

中国国家自然科学基金;

关键词：

CROSS-COUPLING REACTIONS; CARBON-CARBON BONDS; C-C BONDS; TWISTED AMIDES; ARYL KETONES; CYANO BONDS; ACTIVATION; ARYLATION; ESTERS; FUNCTIONALIZATION;

D O I：

10.1039/c8cc03954b

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A sulfur-containing auxiliary enabled palladium-catalyzed C(carbonyl)-C bond activation of amides was reported to form phenylcarbamate derivatives with alcohols. Both alkyl and benzyl alcohols could be employed well with yields up to 85%. Derivations from phenylcarbamates to ureas and thiocarbamates illustrated the potential applications of this sequential C-C cleavage/C-O coupling reaction.

引用

页码：8606 / 8609

页数：4

共 62 条

[1] STRUCTURE OF CYCLOPROPANE PLATINOUS CHLORIDE [J].

ADAMS, DM ;

GUY, RG ;

CHATT, J ;

SHEPPARD, N .

JOURNAL OF THE CHEMICAL SOCIETY, 1961, (FEB) :738-&

[2] Ligand-Controlled Chemoselective C(acyl)-O Bond vs Caryl)-C Bond Activation of Aromatic Esters in Nickel Catalyzed C(sp2)-C(sp3) Cross-Couplings [J].

Chatupheeraphat, Adisak ;

Liao, Hsuan-Hung ;

Srimontree, Watchara ;

Guo, Lin ;

Minenkov, Yury ;

Poater, Albert ;

Cavallo, Luigi ;

Rueping, Magnus .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (10) :3724-3735

[3] Synthesis of Dibenzothiophenes by Pd-Catalyzed Dual C-H Activation from Diaryl Sulfides [J].

Che, Rui ;

Wu, Zhiqing ;

Li, Zhengkai ;

Xiang, Haifeng ;

Zhou, Xiangge .

CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (24) :7258-7261

[4] Recent Advances in Transition-Metal-Catalyzed Functionalization of Unstrained Carbon-Carbon Bonds [J].

Chen, Feng ;

Wang, Teng ;

Jiao, Ning .

CHEMICAL REVIEWS, 2014, 114 (17) :8613-8661

[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] Cu-Catalyzed Three-Component Synthesis of Substituted Benzothiazoles in Water [J].

Deng, Hang ;

Li, Zhengkai ;

Ke, Fang ;

Zhou, Xiangge .

CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (16) :4840-4843

[7] Recent Methodologies That Exploit C-C Single-Bond Cleavage of Strained Ring Systems by Transition Metal Complexes [J].

Fumagalli, Gabriele ;

Stanton, Steven ;

Bower, John F. .

CHEMICAL REVIEWS, 2017, 117 (13) :9404-9432

[8] Organic Carbamates in Drug Design and Medicinal Chemistry [J].

Ghosh, Arun K. ;

Brindisi, Margherita .

JOURNAL OF MEDICINAL CHEMISTRY, 2015, 58 (07) :2895-2940

[9] Ruthenium catalyzed decarbonylative arylation at Sp3 carbon centers in pyrrolidine and piperidine heterocycles [J].

Gribkov, Denis V. ;

Pastine, Stefan J. ;

Schnuerch, Michael ;

Sames, Dalibor .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (38) :11750-11755

[10] Nickel-catalysed retro-hydroamidocarbonylation of aliphatic amides to olefins [J].

Hu, Jiefeng ;

Wang, Minyan ;

Pu, Xinghui ;

Shi, Zhuangzhi .

NATURE COMMUNICATIONS, 2017, 8

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