A Neutral, Chiral, Bis(imidazolidine)-Derived NCN-Type Palladium Pincer Complex with Catalytic Activity

被引:41
作者
Arai, Takayoshi [1 ]
Oka, Ikiyo [1 ]
Morihata, Takuma [1 ]
Awata, Atsuko [1 ]
Masu, Hyuma [2 ]
机构
[1] Chiba Univ, Grad Sch Sci, Dept Chem, Inage Ku, Chiba 2638522, Japan
[2] Chiba Univ, Ctr Chem Anal, Inage Ku, Chiba 2638522, Japan
关键词
asymmetric catalysis; conjugate addition; imidazolidines; palladium; pincer complexes; ENANTIOSELECTIVE MICHAEL ADDITION; C-H ACTIVATION; ALPHA; BETA-UNSATURATED IMIDES; MALONONITRILE; PLATINUM; COORDINATION;
D O I
10.1002/chem.201204017
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Caught in a pincer: A chiral, imidazolidine-derived NCN-type palladium pincer complex has been prepared using a ligand introduction technique. Single-crystal X-ray diffraction analysis of this complex showed a well-organized asymmetric sphere. The neutral palladium/chloride version exhibited significant catalytic activity for the reaction of nitroalkenes with malononitrile to give products in a highly enantioselective manner (see scheme). Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:1554 / 1557
页数:4
相关论文
共 42 条
[1]  
Albrecht M, 2001, ANGEW CHEM INT EDIT, V40, P3750, DOI 10.1002/1521-3773(20011015)40:20<3750::AID-ANIE3750>3.0.CO
[2]  
2-6
[3]  
Albrecht M., 2001, ANGEW CHEM, V113, P3866, DOI DOI 10.1002/1521-3773(20011015)113:20<3866::AID-ANGE3866>3.0.C0
[4]  
2-Y
[5]   Chiral Bis(imidazolidine)pyridine-Cu(OTf)2: Catalytic Asymmetric Endo-Selective [3+2] Cycloaddition of Imino Esters with Nitroalkenes [J].
Arai, Takayoshi ;
Mishiro, Asami ;
Yokoyama, Naota ;
Suzuki, Kuniko ;
Sato, Hiroyasu .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (15) :5338-+
[6]  
Berner OM, 2002, EUR J ORG CHEM, V2002, P1877
[7]   Malononitrile as Acylanion Equivalent [J].
Foerster, Sebastian ;
Tverskoy, Olena ;
Helmchen, Guenter .
SYNLETT, 2008, (18) :2803-2806
[8]   Organocatalytic Enantioselective Michael Addition of Malononitrile to Nitroolefins Catalyzed by Bifunctional Thiourea [J].
Guo, Hai-Ming ;
Li, Jian-Guo ;
Qu, Gui-Rong ;
Zhang, Xiao-Mei ;
Yuan, Wei-Cheng .
CHIRALITY, 2011, 23 (07) :514-518
[9]   Synthesis, characterization and photoluminescent properties of platinum complexes with novel bis(imidazoline) pincer ligands [J].
Hao, Xin-Qi ;
Gong, Jun-Fang ;
Du, Chen-Xia ;
Wu, Li-Yuan ;
Wu, Yang-Jie ;
Song, Mao-Ping .
TETRAHEDRON LETTERS, 2006, 47 (29) :5033-5036
[10]  
Hartwig J.F., 2009, Organotransition Metal Chemistry: From Bonding to Catalysis, V1st