Rearrangement of aldoximes to amides in water under air atmosphere catalyzed by water-soluble iridium complex [Cp*Ir(H2O)3][OTf]2

被引:25
作者
Sun, Chunlou [1 ]
Qu, Panpan [1 ]
Li, Feng [1 ]
机构
[1] Nanjing Univ Sci & Technol, Minist Educ, Key Lab Soft Chem & Funct Mat, Nanjing 210094, Jiangsu, Peoples R China
基金
中国国家自然科学基金;
关键词
DEPENDENT TRANSFER HYDROGENATION; ONE-POT CONVERSION; CP-ASTERISK; N-ALKYLATION; CARBONYL-COMPOUNDS; ALDEHYDES; ALCOHOLS; HYDRATION; HALIDES; PEPTIDES;
D O I
10.1039/c3cy00934c
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
In the presence of the water-soluble iridium complex [Cp*Ir(H2O)(3)][OTf](2), a variety of aldoximes, including aromatic, aliphatic, conjugated unsaturated and non-conjugated unsaturated, were converted into their corresponding amides in water with good to excellent yields. Further, the one-pot synthesis of amides from aldehydes, hydroxylamine hydrochloride and sodium carbonate via a tandem condensation-rearrangement reaction in water was also accomplished. Compared with the reported organometallic catalysts for the rearrangement of aldoximes to amides in water, the present catalyst exhibited some advantages such as being phosphorus ligand-free, having low catalyst loading, and operational convenience under air atmosphere.
引用
收藏
页码:988 / 996
页数:9
相关论文
共 54 条
[1]   Palladium-Catalyzed One-Pot Conversion of Aldehydes to Amides [J].
Ali, Md Ashif ;
Punniyamurthy, Tharmalingam .
ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (2-3) :288-292
[2]   Mechanistic Studies into Metal-Catalyzed Aldoxime to Amide Rearrangements [J].
Allen, C. Liana ;
Lawrence, Ruth ;
Emmett, Liam ;
Williams, Jonathan M. J. .
ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (18) :3262-3268
[3]   Metal-catalysed approaches to amide bond formation [J].
Allen, C. Liana ;
Williams, Jonathan M. J. .
CHEMICAL SOCIETY REVIEWS, 2011, 40 (07) :3405-3415
[4]   Cost efficient synthesis of amides from oximes with indium or zinc catalysts [J].
Allen, C. Liana ;
Burel, Celine ;
Williams, Jonathan M. J. .
TETRAHEDRON LETTERS, 2010, 51 (20) :2724-2726
[5]   Anodic deposition of a robust iridium-based water-oxidation catalyst from organometallic precursors [J].
Blakemore, James D. ;
Schley, Nathan D. ;
Olack, Gerard W. ;
Incarvito, Christopher D. ;
Brudvig, Gary W. ;
Crabtree, Robert H. .
CHEMICAL SCIENCE, 2011, 2 (01) :94-98
[6]   Half-Sandwich Iridium Complexes for Homogeneous Water-Oxidation Catalysis [J].
Blakemore, James D. ;
Schley, Nathan D. ;
Balcells, David ;
Hull, Jonathan F. ;
Olack, Gerard W. ;
Incarvito, Christopher D. ;
Eisenstein, Odile ;
Brudvig, Gary W. ;
Crabtree, Robert H. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (45) :16017-16029
[7]   Selective Hydration of Nitriles to Amides Promoted by an Os-NHC Catalyst: Formation and X-ray Characterization of κ2-Amidate Intermediates [J].
Buil, Maria L. ;
Cadierno, Victorio ;
Esteruelas, Miguel A. ;
Gimeno, Jose ;
Herrero, Juana ;
Izquierdo, Susana ;
Onate, Enrique .
ORGANOMETALLICS, 2012, 31 (19) :6861-6867
[8]   Diphosphino-functionalized MCM-41 anchored palladium(0) complex as an efficient catalyst for Heck arylation of conjugated alkenes with aryl halides [J].
Cai, Mingzhong ;
Sha, Junchao .
CATALYSIS COMMUNICATIONS, 2007, 8 (11) :1691-1696
[9]   Key green chemistry research areas - a perspective from pharmaceutical manufacturers [J].
Constable, David J. C. ;
Dunn, Peter J. ;
Hayler, John D. ;
Humphrey, Guy R. ;
Leazer, Johnnie L., Jr. ;
Linderman, Russell J. ;
Lorenz, Kurt ;
Manley, Julie ;
Pearlman, Bruce A. ;
Wells, Andrew ;
Zaks, Aleksey ;
Zhang, Tony Y. .
GREEN CHEMISTRY, 2007, 9 (05) :411-420
[10]  
Constan A. A., 2004, WO Patent, Patent No. [W02004078169, 2004078169]