Fe-Catalysed oxidative C-H/N-H coupling between aldehydes and simple amides

被引:69
作者
Wang, Jing [1 ]
Liu, Chao [1 ]
Yuan, Jiwen [1 ]
Lei, Aiwen [1 ,2 ]
机构
[1] Wuhan Univ, Coll Chem & Mol Sci, Wuhan 430072, Hubei, Peoples R China
[2] Jiangxi Normal Univ, Natl Res Ctr Carbohydrate Synth, Nanchang 330022, Jiangxi, Peoples R China
基金
高等学校博士学科点专项科研基金; 中国国家自然科学基金;
关键词
EFFICIENT SYNTHESIS; BOND FORMATION; AMIDATION; AMINATION; FUNCTIONALIZATION; ARYLATION; ALKENES; REGIOSELECTIVITY; RUTHENIUM; ADJACENT;
D O I
10.1039/c4cc01447b
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A novel oxidative coupling of aldehydes with simple amides, most likely involving a radical process, was achieved through the use of an iron catalyst. Various amides were utilized as substrates to easily construct imides by coupling with aldehydes. A catalytic cycle involving the benzoyl halide intermediate is proposed based on our experimental results.
引用
收藏
页码:4736 / 4739
页数:4
相关论文
共 56 条
[1]   Intermolecular oxidative cross-coupling of arenes [J].
Ashenhurst, James A. .
CHEMICAL SOCIETY REVIEWS, 2010, 39 (02) :540-548
[2]   Amidation of unfunctionalized hydrocarbons catalyzed by ruthenium cyclic amine or bipyridine complexes [J].
Au, SM ;
Huang, JS ;
Che, CM ;
Yu, WY .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (23) :7858-7864
[3]   Synthesis of Imides by Palladium-Catalyzed C-H Functionalization of Aldehydes with Secondary Amides [J].
Bian, Yong-Jun ;
Chen, Chao-Yue ;
Huang, Zhi-Zhen .
CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (03) :1129-1133
[4]   Iron-catalyzed C-O cross-couplings of phenols with aryl iodides [J].
Bistri, Olivia ;
Correa, Arkaitz ;
Bolm, Carsten .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (03) :586-588
[5]   PALLADIUM-ASSISTED FUNCTIONALIZATION OF OLEFINS - A NEW AMINATION OF ELECTRON-DEFICIENT OLEFINS [J].
BOZELL, JJ ;
HEGEDUS, LS .
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (12) :2561-2563
[6]   Aerobic oxidative amination of unactivated alkenes catalyzed by palladium [J].
Brice, JL ;
Harang, JE ;
Timokhin, VI ;
Anastasi, NR ;
Stahl, SS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (09) :2868-2869
[7]   Overcoming the "Oxidant Problem": Strategies to Use O2 as the Oxidant in Organometallic C-H Oxidation Reactions Catalyzed by Pd (and Cu) [J].
Campbell, Alison N. ;
Stahl, Shannon S. .
ACCOUNTS OF CHEMICAL RESEARCH, 2012, 45 (06) :851-863
[8]   Iron-catalyzed Sonogashira reactions [J].
Carril, Monica ;
Correa, Arkaitz ;
Bolm, Carsten .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (26) :4862-4865
[9]   Rh(II)-Catalyzed intermolecular oxidative sulfamidation of aldehydes:: A mild efficient synthesis of N-sulfonylcarboxamides [J].
Chan, Johann ;
Baucorn, Kyle D. ;
Murry, Jerry A. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (46) :14106-+
[10]   Palladium-catalyzed alkylation of sp2 and sp3 C-H bonds with methylboroxine and alkylboronic acids:: Two distinct C-H activation pathways [J].
Chen, Xiao ;
Goodhue, Charles E. ;
Yu, Jin-Quan .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (39) :12634-12635