Palladium(II) complexes of N-(pyridin-2-yl)-1,2-azol-3-carboxamide derived NNN-pincer ligands: Synthesis, unusual complexation and high-turnover catalysis in water

被引：0

作者：

Bumagin, Nikolay A. ^{[1
]}

Kolesnik, Irina A. ^{[2
]}

Potkin, Vladimir I. ^{[2
]}

Dikusar, Evgeniy A. ^{[2
]}

Lyakhov, Alexander S. ^{[3
]}

Ivashkevich, Ludmila S. ^{[3
]}

Zhou, Hongwei ^{[4
]}

Li, Wenliang ^{[5
]}

机构：

[1] Moscow MV Lomonosov State Univ, Chem Dept, Leninskie Gory 1-3, Moscow 119991, Russia

[2] Natl Acad Sci Belarus, Inst Phys Organ Chem, Surganov Str 13, Minsk 220072, BELARUS

[3] Belarusian State Univ, Res Inst Phys Chem Problems, Leningradskaya Str 14, Minsk 220006, BELARUS

[4] Jiaxing Univ, Jiahang Rd 1, Jiaxing 314001, Zhejiang, Peoples R China

[5] Changchun Univ Sci & Technol, Sch Chem & Environm Engn, Satellite Rd 7989, Changchun 130022, Peoples R China

来源：

POLYHEDRON | 2024年 / 264卷

关键词：

Isoxazole; Isothiazole; 2-Amino(alkyl)pyridines; NNN-pincer ligands; Pd(II) complexes; Catalysis; Green chemistry; SUZUKI-MIYAURA REACTION; COORDINATION CHEMISTRY; ISOXAZOLE; DERIVATIVES; RING;

D O I：

10.1016/j.poly.2024.117249

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Synthesis, characterization, and catalytic activity of palladium(II) complexes containing tridentate N-(pyridin-2yl)-1,2-azol-3-carboxamide ligands with various length amide linkers [CONH(CH2)n, n = 0,1,2] is reported. Complexation of previously undescribed mixed pyridin-azol-carboxamide ligands with PdCl2 occurs unusually by deprotonation of the amide group and elimination of HCl affording the palladium(II) pincer complexes [(k3NNN)PdCl]n (n = 1, 2), which was proven by single crystal X-ray diffraction. The first time synthesized complexes are high-turnover catalysts, as was shown during the evaluation in Suzuki reaction between aryl halides and arylboronic acids: substituted biaryls, including practically significant, were obtained with up to quantitative yields under Green Chemistry conditions.

引用

页数：9

共 31 条

[1] Medicinal Importance and Chemosensing Applications of Pyridine Derivatives: A Review
Abu-Taweel, Gasem Mohammad
Ibrahim, Munjed M.
Khan, Sikandar
Al-Saidi, Hamed M.
Alshamrani, Meshal
Alhumaydhi, Fahad A.
Alharthi, Salman S.
[J]. CRITICAL REVIEWS IN ANALYTICAL CHEMISTRY, 2024, 54 (03) : 599 - 616
[2] Functionalized isoxazole and isothiazole ligands: design, synthesis, palladium complexes, homogeneous and heterogeneous catalysis in aqueous media
Bumagin, N. A.
Potkin, V. I.
[J]. RUSSIAN CHEMICAL BULLETIN, 2016, 65 (02) : 321 - 332
[3] Substituted 1-(isoxazol-3-yl)methyl-1H-1,2,3-triazoles: Synthesis, palladium(II) complexes, and high-turnover catalysis in aqueous media
Bumagin, Nikolay A.
Kletskov, Alexey V.
Petkevich, Sergey K.
Kolesnik, Iryna A.
Lyakhov, Alexander S.
Ivashkevich, Ludmila S.
Baranovsky, Alexander V.
Kurman, Peter V.
Potkin, Vladimir I.
[J]. TETRAHEDRON, 2018, 74 (27) : 3578 - 3588
[4] High-turnover aminopyridine-based Pd-catalysts for Suzuki-Miyaura reaction in aqueous media
Bumagin, Nikolay A.
[J]. CATALYSIS COMMUNICATIONS, 2016, 79 : 17 - 20
[5] Crystal structure determination and refinement via SIR2014
Burla, Maria Cristina
Caliandro, Rocco
Carrozzini, Benedetta
Cascarano, Giovanni Luca
Cuocci, Corrado
Giacovazzo, Carmelo
Mallamo, Mariarosaria
Mazzone, Annamaria
Polidori, Giampiero
[J]. JOURNAL OF APPLIED CRYSTALLOGRAPHY, 2015, 48 : 306 - 309
[6] Neonicotinoids and Other Insect Nicotinic Receptor Competitive Modulators: Progress and Prospects
Casida, John E.
[J]. ANNUAL REVIEW OF ENTOMOLOGY, VOL 63, 2018, 63 : 125 - 144
[7] Design of pincer complexes based on (methylsulfanyl)acetic/propionic acid amides with ancillary S- and N-donors as potential catalysts and cytotoxic agents
Churusova, Svetlana G.
Aleksanyan, Diana V.
Vasil'ev, Andrei A.
Rybalkina, Ekaterina Yu.
Susova, Olga Yu.
Klemenkova, Zinaida S.
Aysin, Rinat R.
Nelyubina, Yulia V.
Kozlov, Vladimir A.
[J]. APPLIED ORGANOMETALLIC CHEMISTRY, 2018, 32 (06)
[8] 5,6-and 6,6-Membered Palladium(II) Pincer Complexes Based on Functionalized Carboxamides with Ancillary Sulfur and Nitrogen Donors
Churusova, Svetlana G.
Aleksanyan, Diana V.
Vasil'ev, Andrei A.
Nelyubina, Yulia V.
Novikov, Valentin V.
Pavlov, Alexander A.
Denisov, Gleb L.
Klemenkova, Zinaida S.
Kozlov, Vladimir A.
[J]. EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2016, (33) : 5271 - 5280
[9] Water-soluble copper(II) complexes with 4,5-dichloro-isothiazole-3-carboxylic acid and heterocyclic N -donor ligands: Synthesis, crystal structures, cytotoxicity, and DNA binding study
Eremina, Julia A.
Lider, Elizaveta, V
Sukhikh, Taisiya S.
Klyushova, Lyubov S.
Perepechaeva, Maria L.
Sheven', Dmitriy G.
Berezin, Alexey S.
Grishanova, Alevtina Y.
Potkin, Vladimir, I
[J]. INORGANICA CHIMICA ACTA, 2020, 510
[10] A PdCl2 complex with isonicotinaldehyde oxime, an efficient catalyst for the Suzuki reaction in aqueous media
Evdokimov, D. V.
Bumagin, N. A.
[J]. RUSSIAN CHEMICAL BULLETIN, 2007, 56 (02) : 369 - 370

← 1 2 3 4 →