Direct Amidation of Alcohols with N-Substituted Formamides under Transition-Metal-Free Conditions

被引:144
作者
Xu, Kun [1 ,2 ]
Hu, Yanbin [1 ,2 ]
Zhang, Sheng [1 ,2 ]
Zha, Zhenggen [1 ,2 ]
Wang, Zhiyong [1 ,2 ]
机构
[1] Univ Sci & Technol China, Hefei Natl Lab Phys Sci Microscale, CAS Key Lab Soft Matter Chem, Hefei 230026, Anhui, Peoples R China
[2] Univ Sci & Technol China, Dept Chem, Hefei 230026, Anhui, Peoples R China
关键词
alcohols; amides; dimethylformamide; radical reactions; transition-metal-free reactions; MONOXIDE-FREE AMINOCARBONYLATION; DIRECT AMIDE SYNTHESIS; CATALYZED CONVERSION; OXIDATIVE AMIDATION; AMBIENT CONDITIONS; BOND FORMATION; ARYL HALIDES; TRANSFER HYDROAMINATION; DIRECT CARBAMOYLATION; PRIMARY CARBOXAMIDES;
D O I
10.1002/chem.201201203
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Go tandem! The first example of the direct amidation of alcohols with N-substituted formamides has been developed. A series of tertiary amides, including the challenging N,N-dimethyl-substituted amides, were obtained in moderate to good yields under transition-metal-free conditions (see scheme). TBHP=tert-butyl hydroperoxide. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:9793 / 9797
页数:5
相关论文
共 97 条
[81]   Efficient hydration of nitriles to amides in water, catalyzed by ruthenium hydroxide supported on alumina [J].
Yamaguchi, K ;
Matsushita, M ;
Mizuno, N .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (12) :1576-1580
[82]  
Yamaguchi K., 2012, ANGEW CHEM, V124, P559
[83]   Heterogeneously Catalyzed Synthesis of Primary Amides Directly from Primary Alcohols and Aqueous Ammonia [J].
Yamaguchi, Kazuya ;
Kobayashi, Hiroaki ;
Oishi, Takamichi ;
Mizuno, Noritaka .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (02) :544-547
[84]   Metal-free intramolecular oxidative decarboxylative amination of primary α-amino acids with product selectivity [J].
Yan, Yizhe ;
Wang, Zhiyong .
CHEMICAL COMMUNICATIONS, 2011, 47 (33) :9513-9515
[85]   Highly efficient oxidative amidation of aldehydes with amine hydrochloride salts [J].
Yoo, Woo-Jin ;
Li, Chao-Jun .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (40) :13064-13065
[86]  
Zhang C., 2011, ANGEW CHEM, V123, P11284
[87]   Copper-Catalyzed Aerobic Oxidative Coupling of Aryl Acetaldehydes with Anilines Leading to a-Ketoamides [J].
Zhang, Chun ;
Xu, Zejun ;
Zhang, Liangren ;
Jiao, Ning .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (47) :11088-11092
[88]   Dioxygen Activation under Ambient Conditions: Cu-Catalyzed Oxidative Amidation-Diketonization of Terminal Alkynes Leading to α-Ketoamides [J].
Zhang, Chun ;
Jiao, Ning .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (01) :28-+
[89]  
Zhang J., 2010, ANGEW CHEM, V122, P6535, DOI DOI 10.1002/ANGE.201002136
[90]   Synthesis of Cyclic Imides from Simple Diols [J].
Zhang, Jian ;
Senthilkumar, Muthaiah ;
Ghosh, Subhash Chandra ;
Hong, Soon Hyeok .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (36) :6391-6395