Chelating palladium complexes containing pyridine/pyrimidine hydroxyalkyl di-functionalized N-heterocyclic carbenes: synthesis, structure, and catalytic activity towards C-H activation

被引:19
作者
Yang, Liangru [1 ]
Yuan, Jinwei [1 ]
Mao, Pu [1 ]
Guo, Qi [1 ]
机构
[1] Henan Univ Technol, Sch Chem & Chem Engn, Zhengzhou 450001, Peoples R China
基金
中国国家自然科学基金;
关键词
HIGHLY EFFICIENT; CHLORIDE COMPLEXES; PLATINUM COMPLEXES; DIRECT ARYLATION; LIGANDS; RHODIUM; HYDROGENATION; BENZOXAZOLES; PRECURSORS; CHEMISTRY;
D O I
10.1039/c5ra21183b
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The synthesis of novel chelating palladium complexes containing pyridine/pyrimidine hydroxyalkyl di-functionalized N-heterocyclic carbenes (NHCs) via direct metallation of the precursor imidazolium salts is presented. The structure has been characterized unambiguously by X-ray single crystal analysis. Catalytic activity investigation showed that the complexes catalyse the direct C-H bond arylation of (benzo)oxazoles efficiently when using (BuOLi)-Bu-t as base and DMF as solvent.
引用
收藏
页码:107601 / 107607
页数:7
相关论文
共 82 条
[1]   Extension of the alkane bridge in BisNHC-Palladium-Chloride complexes. Synthesis, structure, and catalytic activity [J].
Ahrens, Sebastian ;
Zeller, Alexander ;
Taige, Maria ;
Strassner, Thomas .
ORGANOMETALLICS, 2006, 25 (22) :5409-5415
[2]   One-step synthesis of 2-arylbenzothiazole ('BTA') and -benzoxazole precursors for in vivo imaging of β-amyloid plaques [J].
Alagille, D ;
Baldwin, RM ;
Tamagnan, GD .
TETRAHEDRON LETTERS, 2005, 46 (08) :1349-1351
[3]   A STABLE CRYSTALLINE CARBENE [J].
ARDUENGO, AJ ;
HARLOW, RL ;
KLINE, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (01) :361-363
[4]   SYNTHESIS OF A REVERSE YLIDE FROM A NUCLEOPHILIC CARBENE [J].
ARDUENGO, AJ ;
KLINE, M ;
CALABRESE, JC ;
DAVIDSON, F .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (25) :9704-9705
[5]  
Arockiam PB, 2012, CHEM REV, V112, P5879, DOI [10.1021/cr300153j, 10.1021/cr300153J]
[6]   Synthesis and characterization of N-heterocyclic carbene palladium complex and its application on direct arylation of benzoxazoles and benzothiazoles with aryl bromides [J].
Arslan, Hakan ;
Ozdemir, Ismail ;
Vanderveer, Don ;
Demir, Serpl ;
Cetinkaya, Bekir .
JOURNAL OF COORDINATION CHEMISTRY, 2009, 62 (16) :2591-2599
[7]   Sulfur-functionalized N-heterocyclic carbenes and their transition metal complexes [J].
Bierenstiel, Matthias ;
Cross, Edward D. .
COORDINATION CHEMISTRY REVIEWS, 2011, 255 (5-6) :574-590
[8]   Stereochemical and structural characteristics of single- and double-site Pd(II)-N-heterocyclic carbene complexes: Promising catalysts in organic syntheses ranging from C-C coupling to olefin polymerizations [J].
Budagumpi, Srinivasa ;
Haque, Rosenani A. ;
Salman, Abbas Washeel .
COORDINATION CHEMISTRY REVIEWS, 2012, 256 (17-18) :1787-1830
[9]   A Radical Process towards the Development of Transition-Metal-Free Aromatic Carbon-Carbon Bond-Forming Reactions [J].
Chan, Tek Long ;
Wu, Yinuo ;
Choy, Pui Ying ;
Kwong, Fuk Yee .
CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (47) :15802-15814
[10]   Simple, efficient and reusable Pd-NHC catalysts for hydroamination [J].
Chen, Qian ;
Lv, Lanlan ;
Yu, Meng ;
Shi, Yanhui ;
Li, Yuling ;
Pang, Guangsheng ;
Cao, Changsheng .
RSC ADVANCES, 2013, 3 (40) :18359-18366