Highly efficient ruthenium(II) porphyrin catalyzed amidation of aldehydes

被引:162
作者
Chang, Joyce Wei Wei [1 ]
Chan, Philip Wai Hong [1 ]
机构
[1] Nanyang Technol Univ, Sch Math & Phys Sci, Div Chem & Biol Chem, Singapore 637371, Singapore
关键词
alclehydes; amide bond formation; C-H activation; homogeneous catalysis; ruthenium;
D O I
10.1002/anie.200704695
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
H to N: The first example of a mild, highly efficient C-H bond amidation catalyzed by ruthenium(II) porphyrin complexes uses PhI=NTs as the nitrogen source for installing the amide bond functionality in a wide variety of aldehydes (see scheme). The protocol is chemoselective, with the new C-N bond forming only at the acyl C-H bond, even in aldehyde substrates containing other functional groups. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:1138 / 1140
页数:3
相关论文
共 54 条
[21]   Synthesis of 1,3-difunctionalized amine derivatives through selective C-H bond oxidation [J].
Espino, CG ;
Wehn, PM ;
Chow, J ;
Du Bois, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (28) :6935-6936
[22]  
Fraxedas J, 2006, MOL ORGANIC MAT MOL
[23]   Facile amine formation by intermolecular catalytic amidation of carbon-hydrogen bonds [J].
Fructos, Manuel R. ;
Trofimenko, Swiatoslaw ;
Diaz-Requejo, M. Mar ;
Perez, Pedro J. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (36) :11784-11791
[24]   A unique and highly efficient method for catalytic olefin aziridination [J].
Guthikonda, K ;
Du Bois, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (46) :13672-13673
[25]   Ruthenium(II) porphyrin-catalyzed amidation of aromatic heterocycles [J].
He, L ;
Chan, PWH ;
Tsui, WM ;
Yu, WY ;
Che, CM .
ORGANIC LETTERS, 2004, 6 (14) :2405-2408
[26]   Chemical synthesis of natural product peptides: Coupling methods for the incorporation of noncoded amino acids into peptides [J].
Humphrey, JM ;
Chamberlin, AR .
CHEMICAL REVIEWS, 1997, 97 (06) :2243-2266
[27]  
Jacobsen E. N., 1999, COMPREHENSIVE ASYMME, V2, P607
[28]  
Kleeman A., 2001, PHARM SUBSTANCES SYN
[29]   The regio- and stereoselective one-pot catalytic preparation of β-selenyl acrylamides [J].
Knapton, DJ ;
Meyer, TY .
ORGANIC LETTERS, 2004, 6 (05) :687-689
[30]  
Larock R.C., 1989, COMPREHENSIVE ORGANI