Mimics of Pincer Ligands: An Accessible Phosphine-Free N-(Pyrimidin-2-yl)-1,2-azole-3-carboxamide Framework for Binuclear Pd(II) Complexes and High-Turnover Catalysis in Water

被引:22
作者
Kletskov, Alexey, V [1 ,2 ,3 ,4 ]
Bumagin, Nikolay A. [1 ]
Petkevich, Sergey K. [2 ]
Dikusar, Evgenij A. [2 ]
Lyakhov, Alexander S. [5 ]
Ivashkevich, Ludmila S. [5 ]
Kolesnik, Iryna A. [2 ]
Potkin, Vladimir, I [2 ]
机构
[1] Moscow MV Lomonosov State Univ, Chem Dept, Moscow 119991, Russia
[2] Natl Acad Sci Belarus, Inst Phys Organ Chem, Minsk 220072, BELARUS
[3] Natl Acad Sci Belarus, Minsk 220072, BELARUS
[4] Peoples Friendship Univ Russia RUDN Univ, Moscow 117198, Russia
[5] Belarusian State Univ, Res Inst Phys Chem Problems, Minsk 220006, BELARUS
基金
俄罗斯基础研究基金会;
关键词
CROSS-COUPLING REACTIONS; FUNCTIONALIZED NITROGEN LIGANDS; SUZUKI-MIYAURA REACTION; ORGANOBORON COMPOUNDS; ACID-DERIVATIVES; PALLADIUM; ISOTHIAZOLE; CHEMISTRY; ISOXAZOLE;
D O I
10.1021/acs.inorgchem.0c01035
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
We report for the first time cyclic phosphine-free "head to tail" N,N,N pincer-like (pincer complexes mimicking) N-(pyrimidin-2-yl)-1,2-azole-3-carboxamide Pd(II) complexes with deprotonated amide groups as high-turnover catalysts (TON up to 10(6), TOF up to 1.2 x 10(7) h(-1)) for cross-coupling reactions on the background of up to quantitative yields under Green Chemistry conditions. The potency of the described catalyst family representatives was demonstrated in Suzuki-Miyaura, Mizoroki-Heck, and Sonogashira reactions on industrially practical examples. Corresponding ligands could be synthesized based on readily available reagents through simple chemical transformations. Within the complex structures, a highly unusual 1,3,5,7-tetraza-2,6-dipalladocane frame could be observed.
引用
收藏
页码:10384 / 10388
页数:5
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