N,N-dimethyl-β-alanine as an inexpensive and efficient ligand for palladium-catalyzed Heck reaction

被引:126
作者
Cui, Xin [1 ]
Li, Zhe [1 ]
Tao, Chuan-Zhou [1 ]
Xu, Yu [1 ]
Li, Juan [1 ]
Liu, Lei [1 ]
Guo, Qing-Xiang [1 ]
机构
[1] Univ Sci & Technol China, Dept Chem, Hefei 230026, Peoples R China
关键词
D O I
10.1021/ol060585n
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
N, N-Dimethyl-ss-alanine was found to be a more powerful phosphine-free ligand than the previously reported ligand, N, N-dimethylglycine, in the Pd-catalyzed Heck reaction for a variety of aryl bromides, aryl iodides, and activated aryl chlorides with a practical turnover number of 10(3). Both kinetic and theoretical studies suggested that N, N-dimethyl-ss-alanine led to faster oxidative addition of an aryl halide to Pd than N, N-dimethylglycine.
引用
收藏
页码:2467 / 2470
页数:4
相关论文
共 41 条
[11]   FINE FEATHERS MAKE FINE BIRDS - THE HECK REACTION IN MODERN GARB [J].
DE MEIJERE, A ;
MEYER, FE .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1994, 33 (23-24) :2379-2411
[12]   A unifying mechanism for all high-temperature Heck reactions. The role of palladium colloids and anionic species [J].
de Vries, JG .
DALTON TRANSACTIONS, 2006, (03) :421-429
[13]   Copper-catalyzed cross-coupling of sulfonamides with aryl iodides and bromides facilitated by amino acid ligands [J].
Deng, W ;
Liu, L ;
Zhang, C ;
Liu, M ;
Guo, QX .
TETRAHEDRON LETTERS, 2005, 46 (43) :7295-7298
[14]   CuI-catalyzed coupling reactions of aryl iodides and bromides with thiols promoted by amino acid ligands [J].
Deng, W ;
Zou, Y ;
Wang, YF ;
Liu, L ;
Guo, QX .
SYNLETT, 2004, (07) :1254-1258
[15]   Amino acid-mediated Goldberg reactions between amides and aryl iodides [J].
Deng, W ;
Wang, YF ;
Zou, W ;
Liu, L ;
Guo, QX .
TETRAHEDRON LETTERS, 2004, 45 (11) :2311-2315
[16]   Synthesis and reactivity of palladium and nickel β-diimine complexes:: Application as catalysts for Heck, Suzuki, and Hiyama coupling reactions [J].
Domin, D ;
Benito-Garagorri, D ;
Mereiter, K ;
Fröhlich, J ;
Kirchner, K .
ORGANOMETALLICS, 2005, 24 (16) :3957-3965
[17]   Novel cationic and neutral Pd(II) complexes bearing imidazole based chelate ligands:: synthesis, structural characterisation and catalytic behaviour [J].
Done, MC ;
Rüther, T ;
Cavell, KJ ;
Kilner, M ;
Peacock, EJ ;
Braussaud, N ;
Skelton, BW ;
White, A .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2000, 607 (1-2) :78-92
[18]   The asymmetric intramolecular Heck reaction in natural product total synthesis [J].
Dounay, AB ;
Overman, LE .
CHEMICAL REVIEWS, 2003, 103 (08) :2945-2963
[19]   High-turnover palladium catalysts in cross-coupling and Heck chemistry: A critical overview [J].
Farina, V .
ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (13-15) :1553-1582
[20]  
Frisch M.J., 2004, Gaussian 03