Photoaccelerated energy transfer catalysis of the Suzuki–Miyaura coupling through ligand regulation on Ir(<scp>iii</scp>)–Pd(<scp>ii</scp>) bimetallic complexes

Yao, Su‐Yang; Cao, Ming; Zhang, Xiulian

doi:10.1039/d0ra08547b

Cited by 8 publications

(2 citation statements)

References 67 publications

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“…The advantages of the dinuclear photoactive complexes was thoroughly studied in such processes as hydrogen photogeneration [17][18][19] , CO 2 photoreduction 14,20,21 and photoaccelerated polymerization [22][23][24][25] . In recent years Ir-Pd 26,27 , Ru-Pd 28,29 , Ru-Au 30 , Ru-Cu 31,32 and Ir-Ni 33 dinuclear complexes have been successfully employed for the oxydation reactions and carbon-carbon and carbon-element bond formation reactions under visible light irradiation. The structure of the bridging ligand is one of the most important parameters controlling the interaction between the photocatalyst and the metal complex catalyst in the dinuclear complex and thus governing the efficiency of the dual catalyst.…”

Section: Introductionmentioning

confidence: 99%

Ru(II)–Pd(II) dinuclear complexes of di(pyridin-2-yl)amino-substituted 1,10-phenanthrolines: synthesis, characterization and application for catalysis

Ionova,

Dmitrieva,

Abel

et al. 2024

Preprint

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Dinuclear complexes bearing Ru(II) photoactive center are of interest for the development of efficient dual catalysts for many photocatalyzed reactions. Ditopic polypyrine ligands – bis(pyridine-2-yl)amino-1,10-phenanthrolines – containing additional coordination site (bis(pyridine-2-yl)amine, dpa) at positions 3, 4 or 5 of 1,10-phenanthroline core (Phen-3NPy2, Phen-4NPy2 and Phen-5NPy2) were synthesized. They were used as bridging ligands to obtain dinuclear complexes of composition [(bpy)2Ru(Phen-NPy2)PdCl2](PF6)2 (Ru(Phen-NPy2)Pd) via stepvise comlexing in good yields. Ru(II) is coordinated to 1,10-phenanthroline in these complexes, while Pd(II) is bound to dpa chelating moiety, which was established by NMR spectroscopy and X-ray single crystal analysis. The influence of the position of dpa in phenanthroline ring on the structural, optical and electrochemical properties of Ru(Phen-NPy2)Pd complexes was studied. The complexes possess photoluminescence in argon-saturated MeCN solution with maxima in the range of 615–625 nm, emission quantum yields range from 0.11 to 0.15 for Ru(Phen-NPy2) complexes and from 0.018 to 0.026 for dinucear Ru(Phen-NPy2)Pd complexes. All the complexes have high extinction coefficients in the range of 370–470 nm, efficiently absorb visible light and can be used as photocatalysts. The Ru2+/3+ potential in Ru(Phen-NPy2)Pd complexes showed no significant dependence on dpa position, while Pd2+/0 reduction potential was quite lower for Ru(Phen-3NPy2)Pd and Ru(Phen-NPy2)Pd, than for Ru(Phen-NPy2)Pd (–0.57V and –0.72V vs Ag/AgCl, KCl(sat), respectively). The behaviour of the complexes was studied in Сu-free Sonogashira coupling under blue LED (12 W) irradiation. The reaction proceeds three times faster when Ru(Phen-4NPy2)Pd and Ru(Phen-3NPy2)Pd are used as catalysts precursors than in the case of mixed catalytic system Ru(bpy)3(PF6)2/(RNPy2)PdCl2.

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Section: Introductionmentioning

confidence: 99%

Ru(II)–Pd(II) dinuclear complexes of di(pyridin-2-yl)amino-substituted 1,10-phenanthrolines: synthesis, characterization and application for catalysis

Ionova,

Dmitrieva,

Abel

et al. 2024

Preprint

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“…Interestingly, several nitrogenated ligands have been also employed for the Suzuki-Miyaura cross-coupling. We can quote for example the use of Schiff bases [44][45][46][47][48][49][50], amines [51,52], azo compounds [53], pyridines [54][55][56][57][58], pyrimidines [59,60], triazoles [61] or benzimidazoles [62]. However, despite their relevance, these catalytic systems suffer from one or more drawbacks such as the use of expensive or difficultly accessible ligands, as well as high catalyst loading, hazardous solvents and harsh reaction conditions.…”

Section: Introductionmentioning

confidence: 99%

Palladium-catalyzed Suzuki–Miyaura cross-coupling with α-aminophosphonates based on 1,3,4-oxadiazole as ligands

Hkiri¹,

Touil²,

Samarat³

et al. 2022

Comptes Rendus. Chimie

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The synthesis of a palladium complex bearing two diethyl[(5-phenyl-1,3,4-oxadiazol-2ylamino)(4-nitrophenyl)methyl]phosphonates as ligands has demonstrated the ability of this type of α-aminophosphonates to coordinate to the palladium(II) ion via their electronically enriched nitrogen atom of the 1,3,4-oxadiazole ring. The complex was fully characterized by elemental analysis, infrared, NMR and mass spectrometry. A solid-state structure revealed the trans coordination of the two nitrogenated ligands. The presence of a hemilabile P(O)(OEt) 2 moiety in the α-aminophosphonates was exploited into palladium-catalyzed Suzuki-Miyaura cross-coupling of aryl halides. The formation of (N ,O)-chelate intermediates may increase the steric hindrance and the electronic density of the metal, which should favor the oxidative addition and the reductive elimination/product decoordination elementary steps. With our catalytic systems, good activities for the formation of orthodi/trisubstituted biphenyl compounds were observed from aryl bromides using only 0.5 mol% of palladium. Cross-coupling of aryl chlorides required a catalyst loading of 1 mol% to generate orthosubstituted biphenyls.

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Hybrid Catalysts in Photoredox Arylation of Sodium Arylsulfinates

Ionova,

Abel,

Averin

et al. 2024

Adv Synth Catal

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Complexes [(bpy)2Ru(BL)](PF6)2 (Ru(BL), BL = N,N‐di(pyridin‐2‐yl)‐1,10‐phenanthrolinamine) have been investigated in the coupling reaction of aryl halides and sodium arylsulfinates under visible light irradiation. The position (3, 4 or 5) of the nickel‐coordinating di(pyridin‐2‐yl)amine fragment in the 1,10‐phenanthroline system has a strong influence on the activity of the catalytic system. The advantage of binding fragments of photocatalyst and metal complex into one molecule in the systems with bridging ligands N,N‐di(pyridin‐2‐yl)‐1,10‐phenanthrolin‐3‐amine (BL1) and N,N‐di(pyridin‐2‐yl)‐1,10‐phenanthrolin‐4‐amine (BL2), in comparison with mixed catalytic systems, is shown. With Ru(BL2) photocatalysts it is possible to reduce the loading to 0.1 mol%, instead of the commonly used 1–2 mol%, and to eliminate the use of the additional ligand for nickel. Under these conditions, more than 20 diarylsulfones of different structures were synthesized in 25–95%yields.

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Photoaccelerated energy transfer catalysis of the Suzuki–Miyaura coupling through ligand regulation on Ir(iii)–Pd(ii) bimetallic complexes

Abstract: A series bimetallic catalysts were synthesized. Relationship between the structure of catalysts and catalytic reactivities were studied and improvement of the catalytic efficiency for Suzuki–Miyaura coupling was accomplished by regulating their chromophores.

Cited by 8 publications

References 67 publications

Ru(II)–Pd(II) dinuclear complexes of di(pyridin-2-yl)amino-substituted 1,10-phenanthrolines: synthesis, characterization and application for catalysis

Ru(II)–Pd(II) dinuclear complexes of di(pyridin-2-yl)amino-substituted 1,10-phenanthrolines: synthesis, characterization and application for catalysis

Palladium-catalyzed Suzuki–Miyaura cross-coupling with α-aminophosphonates based on 1,3,4-oxadiazole as ligands

Hybrid Catalysts in Photoredox Arylation of Sodium Arylsulfinates

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