Palladium mediated activation of C-F bonds in 2,4,6-trifluoropyrimidine: Synthesis and structure of palladium pyrimidyloxy and pyrimidinone derivatives

被引:23
作者
Braun, T [1 ]
Schorlemer, V [1 ]
Neumann, B [1 ]
Stammler, HG [1 ]
机构
[1] Univ Bielefeld, Fak Chem, D-33501 Bielefeld, Germany
关键词
palladium; binuclear compounds; fluorinated heterocycles; C-F activation;
D O I
10.1016/j.jfluchem.2005.12.025
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
[PdMe2(dcpm)] (1) reacts with 2,4,6-trifluoropyrimidine in the presence of water to give the palladium derivative [PdMe{4-C4N2F2H(=O)}(dcpm)] (2). When additional triethylamine is present complex [PdMe(2-OC4N2F2H)(dcpm)] (4) in addition to 2 is formed. Compound 2 converts slowly into the binuclear complex [Pd(4-C4N2F2H(=O)}(mu-dcpm]2 (5). The molecular structure of 5 was determined by X-ray crystallography. The palladium-palladium distance is 2.5898(3)angstrom. (c) 2006 Elsevier B.V. All rights reserved.
引用
收藏
页码:367 / 372
页数:6
相关论文
共 54 条
[1]   Efficient aryl-(hetero)aryl coupling by activation of C-Cl and C-F bonds using nickel complexes of air-stable phosphine oxides [J].
Ackermann, L ;
Born, R ;
Spatz, JH ;
Meyer, D .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (44) :7216-7219
[2]  
Ackermann L., 2005, ANGEW CHEM, V117, P7382
[3]   Synthesis, structure, and properties of {((t)Bu(2)PC(2)H(4)P(t)Bu(2))Ni}(2)(mu-eta(2):eta(2)-C6H6) and ((t)Bu(2)PC(2)H(4)P(t)Bu(2))Ni(eta(2)-C6F6) [J].
Bach, I ;
Porschke, KR ;
Goddard, R ;
Kopiske, C ;
Kruger, C ;
Rufinska, A ;
Seevogel, K .
ORGANOMETALLICS, 1996, 15 (23) :4959-4966
[4]   PYRIMIDINONES AS REVERSIBLE METAPHASE ARRESTING AGENTS [J].
BENNECHE, T ;
STRANDE, P ;
OFTEBRO, R ;
UNDHEIM, K .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1993, 28 (06) :463-472
[5]  
Bohm V. P. W., 2001, ANGEW CHEM, V113, P3500
[6]  
Böhm VPW, 2001, ANGEW CHEM INT EDIT, V40, P3387
[7]   Routes to unique palladium A-frame complexes with a bridging fluoro-ligand [J].
Braun, T ;
Steffen, A ;
Schorlemer, V ;
Neumann, B ;
Stammler, HG .
DALTON TRANSACTIONS, 2005, (20) :3331-3336
[8]   Palladium mediated activation of a C-F bond in pentafluoropyridine: synthesis, structure and reactivity of a pyridyloxy complex [J].
Braun, T ;
Rothfeld, S ;
Schorlemer, V ;
Stammler, A ;
Stammler, HG .
INORGANIC CHEMISTRY COMMUNICATIONS, 2003, 6 (06) :752-755
[9]   Routes to fluorinated organic derivatives by nickel mediated C-F activation of heteroaromatics [J].
Braun, T ;
Perutz, RN .
CHEMICAL COMMUNICATIONS, 2002, (23) :2749-2757
[10]  
Braun T, 2002, ANGEW CHEM INT EDIT, V41, P2745, DOI 10.1002/1521-3773(20020802)41:15<2745::AID-ANIE2745>3.0.CO