Tetranuclear Palladium Complexes of Abnormal N-Heterocyclic Carbene Ligands and their Catalytic Activities in Mizoroki-Heck Coupling Reaction of Electron-Rich Aryl Chlorides

被引:17
作者
Lee, Jhen-Yi [1 ]
Su, Yong-Siang [1 ]
Wang, Yu-Shan [1 ]
Lee, Hon Man [1 ]
机构
[1] Natl Changhua Univ Educ, Dept Chem, Changhua 50058, Taiwan
关键词
Carbene ligand; Palladium; C-C coupling; Heck reaction; Tridentate ligands; SUZUKI-MIYAURA; C-C; PHOSPHA-PALLADACYCLES; IMIDAZOLIUM SALTS; EFFICIENT; ACTIVATION; NANOPARTICLES; SONOGASHIRA; SELECTIVITY; BIDENTATE;
D O I
10.1002/adsc.201900805
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Based on the ligand scaffold of an imidazolyl/benziimidazolyl moiety and a N-CH2C(=O)NHPh substituent, two series of ligand precursors with ortho hydroxy groups incorporated on the N-phenyl rings were prepared. The structural fine tuning of the ligand scaffold allowed the synthesis of tetranuclear palladium complexes with abnormal N-heterocyclic carbene (aNHC) ligands. For precursors with C2-methyl blocking groups, pyridine-assisted C-H bond activation led to the formation of mononuclear tridentate palladium aNHC complexes or tetranuclear complexes with tridentate CNO donors. Representative mononuclear and tetranuclearpalladium aNHC complexes were structurally characterized by X-ray diffraction studies, revealing very short Pd-C bond distances. The tetranuclear palladium aNHC complexes were very effective in catalyzing Mizoroki-Heck coupling reaction, and were capable of employing a range of aryl chlorides including deactivated substrates with low palladium loading of 0.2 mol%.
引用
收藏
页码:4714 / 4726
页数:13
相关论文
共 84 条
[1]   General Reaction Conditions for the Palladium-Catalyzed Vinylation of Aryl Chlorides with Potassium Alkenyltrifluoroborates [J].
Alacid, Emilio ;
Najera, Carmen .
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (21) :8191-8195
[2]  
[Anonymous], 2009, ANGEW CHEM-GER EDIT
[3]   An anion-dependent switch in selectivity results from a change of C-H activation mechanism in the reaction of an imidazolium salt with IrH5(PPh3)2 [J].
Appelhans, LN ;
Zuccaccia, D ;
Kovacevic, A ;
Chianese, AR ;
Miecznikowski, JR ;
Macchioni, A ;
Clot, E ;
Eisenstein, O ;
Crabtree, RH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (46) :16299-16311
[4]   Platinum-mediated oxidative addition and reductive elimination of imidazolium salts at C4 and C5 [J].
Bacciu, D ;
Cavell, KJ ;
Fallis, IA ;
Ooi, LL .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (33) :5282-5284
[5]  
Bacciu D., 2005, ANGEW CHEM, V117, P5416
[6]   The development of palladium catalysts for C-C and C-heteroatom bond forming reactions of aryl chloride substrates [J].
Bedford, RB ;
Cazin, CSJ ;
Holder, D .
COORDINATION CHEMISTRY REVIEWS, 2004, 248 (21-24) :2283-2321
[7]   The heck reaction as a sharpening stone of palladium catalysis [J].
Beletskaya, IP ;
Cheprakov, AV .
CHEMICAL REVIEWS, 2000, 100 (08) :3009-3066
[8]   Rationally designed pincer-type Heck catalysts bearing aminophosphine substituents:: PdIV intermediates and palladium nanoparticles [J].
Bolliger, Jeanne L. ;
Blacque, Olivier ;
Frech, Christian M. .
CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (26) :7969-7977
[9]   Rational Design of Ligand Precursors to Prepare Abnormal (Mesoionic) and Normal Carbene Complexes and Zwitterionic CX-Type Palladacycles (X= C, N) [J].
Chen, Shih-Ji ;
Lin, Yuan-Deng ;
Chiang, Yen-Hsin ;
Lee, Hon Man .
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2014, 2014 (09) :1492-1501
[10]   Abnormal C5-bound N-heterocyclic carbenes: Extremely strong electron donor ligands and their iridium(I) and iridium(III) complexes [J].
Chianese, AR ;
Kovacevic, A ;
Zeglis, BM ;
Faller, JW ;
Crabtree, RH .
ORGANOMETALLICS, 2004, 23 (10) :2461-2468