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

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 12期

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

页码：2467 / 2470

页数：4

共 41 条

[1] Non-conventional methodologies for transition-metal catalysed carbon-carbon coupling: a critical overview. Part 1: The Heck reaction [J].

Alonso, F ;

Beletskaya, IP ;

Yus, M .

TETRAHEDRON, 2005, 61 (50) :11771-11835

[2] Anionic Pd(0) and Pd(II) intermediates in palladium-catalyzed Heck and cross-coupling reactions [J].

Amatore, C ;

Jutand, A .

ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (05) :314-321

[3]

[Anonymous], ADV SYNTH CATAL

[4] Palladacyclic catalysts in C-C and C-heteroatom bond-forming reactions [J].

Bedford, RB .

CHEMICAL COMMUNICATIONS, 2003, (15) :1787-1796

[5] The heck reaction as a sharpening stone of palladium catalysis [J].

Beletskaya, IP ;

Cheprakov, AV .

CHEMICAL REVIEWS, 2000, 100 (08) :3009-3066

[6] Bis(pyrimidine)-based palladium catalysts: synthesis, X-ray structure and applications in Heck-, Suzuki-, Sonogashira-Hagihara couplings and amination reactions [J].

Buchmeiser, MR ;

Schareina, T ;

Kempe, R ;

Wurst, K .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 634 (01) :39-46

[7] Access to well-defined heterogeneous catalytic systems via ring-opening metathesis polymerization (ROMP): Applications in palladium(II)-mediated coupling reactions [J].

Buchmeiser, MR ;

Wurst, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (48) :11101-11107

[8] 1,10-PHENANTHROLINE DERIVATIVES - A NEW LIGAND CLASS IN THE HECK REACTION - MECHANISTIC ASPECTS [J].

CABRI, W ;

CANDIANI, I ;

BEDESCHI, A ;

SANTI, R .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (26) :7421-7426

[9] The design and synthesis of bis(thiourea) ligands and their application in Pd-catalyzed Heck and Suzuki reactions under aerobic conditions [J].

Chen, W ;

Li, R ;

Han, B ;

Li, BJ ;

Chen, YC ;

Wu, Y ;

Ding, LS ;

Yang, D .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (05) :1177-1184

[10] A novel thiourea ligand applied in the Pd-catalyzed Heck, Suzuki and Suzuki carbonylative reactions [J].

Dai, MJ ;

Liang, B ;

Wang, CH ;

You, ZJ ;

Xiang, J ;

Dong, GB ;

Chen, JH ;

Yang, Z .

ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (13-15) :1669-1673

← 1 2 3 4 5 →