Efficient Palladium-catalyzed Suzuki–Miyaura reactions using phenolic Schiff base ligands under ambient conditions in aqueous media

Zhou, Zhonggao; Zhou, Zhenyun; Chen, Aichen; Zhou, Xiaofeng; Qi, Qi; Xie, Yong‐Rong

doi:10.1007/s11243-013-9704-x

Cited by 13 publications

(2 citation statements)

References 33 publications

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“…In addition, their fluorescent properties can be utilized for analytical and imaging purposes . In particular, Schiff base complexes of palladium proved to be active catalysts for hydrogenation and oxidation and in various C–C coupling reactions …”

Section: Introductionmentioning

confidence: 99%

Hydrogenation and Redox Isomerization of Allylic Alcohols Catalyzed by a New Water-Soluble Pd–tetrahydrosalen Complex

Voronova

Purgel²,

Udvardy

et al. 2013

Organometallics

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For applications in aqueous media, sulfonated tetrahydrosalen (sulfosalan, HSS) was synthesized by sulfonation of tetrahydrosalen in fuming sulfuric acid. The Pd(II) complex of this ligand, [Pd(HSS)], showed outstanding activity in hydrogenation and redox isomerization of allylic alcohols in homogeneous aqueous solutions or in aqueous−organic biphasic systems (for oct-1-en-3-ol TOF(hydrogenation) = 1580 h −1 , TOF(redox isomerization) = 400 h −1 ). DFT calculations revealed that H 2 is activated heterolytically, resulting in a Pd(II)−hydride complex, [Pd(H)(HSS-Hphen)], in which one of the phenolate oxygens is protonated. Both hydrogenation and redox isomerization take place via concerted transfer of a proton and a hydride from the hydrogenated catalyst to the allylic alcohol.

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Section: Introductionmentioning

confidence: 99%

Hydrogenation and Redox Isomerization of Allylic Alcohols Catalyzed by a New Water-Soluble Pd–tetrahydrosalen Complex

Voronova

Purgel²,

Udvardy

et al. 2013

Organometallics

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“…Bourland et al reported a chiral tridentate ligand for vanadium metal salts; the catalysts were used in asymmetric selenide oxidation with in situ [2, 3] sigmatropic rearrangement . Although extensive research has been conducted on palladium complexes with [NNO]-, − [ONO]-, − and [CNO]-type − tridentate ligands, there are only limited examples of palladium complexes possessing chiral tridentate ligands. , Therefore, we envisioned that the synthesis and application of such complexes would be a valuable research topic. Although extensive research has been conducted on palladium complexes with [NNO]-, − [ONO]-, − and [CNO]-type − tridentate ligands, there are only limited examples of palladium complexes possessing chiral tridentate ligands − More importantly, to the best of our knowledge, there is no report on palladium complexes possessing chiral [ONO]-type tridentate ligands …”

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confidence: 99%

Selective Formation of Mononuclear Palladium and Acetonitrile-Bridged Dinuclear Palladium Complexes Containing a Chiral Tridentate Ligand

et al. 2021

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From the chiral Schiff base tridentate ligand L Ph , unusual acetonitrile-bridged dinuclear palladium complex 1 and organopalladium complex 1′ were synthesized selectively by using acetonitrile and ethanol, respectively. The chiral tridentate Schiff base ligand was bound to the palladium metal center with different chelation modes ([ONO] for 1 and [CNO] for 1′). Complex 1 constitutes the first example of dinuclear metal complexes connected only by a bridging acetonitrile, in which an exceptionally short CN bond distance [0.945( 12) Å] of bridged acetonitrile was observed. To study the influence of a phenyl group attached to an imine, the phenyl-free ligand L H was prepared and used. In that case, an acetonitrile bridge was not observed. Theoretical calculation studies supporting the formation of 1 and 1′ are favored. * sı Supporting InformationThe Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.inorgchem.1c03391.Experimental procedures, analytical data of the complexes with 1 H NMR, IR, and MS spectra of 1, 1′, and 2, X-ray crystallographic data for 1, 1′, and 2, and density functional theory calculations (PDF)Accession Codes CCDC 2043775, 2043777, and 2095625 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk

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An acetatopalladium(II) complex with 1‐benzyl‐N‐(3,5‐di‐tert‐butylsalicylidene)piperidin‐4‐amine: Synthesis, structure and catalytic applications in Suzuki–Miyaura coupling of arylboronic acids with hydroxyaryl halides

Keesara

Babu

Pal

2017

Applied Organom Chemis

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The Schiff base 1‐benzyl‐N‐(3,5‐di‐tert‐butylsalicylidene)piperidin‐4‐amine (HL) and its acetatopalladium(II) complex having the formula [Pd(L)(OAc)] were synthesized. Both HL and [Pd(L)(OAc)] were characterized using elemental analysis and various spectroscopic (infrared, UV–visible, 1H NMR and 13C NMR) and mass spectrometric measurements. The molecular structure of the complex was determined using X‐ray crystallographic analysis. In the complex, the pincer‐like NNO‐donor L− and the monodenate OAc− provide a distorted square‐planar N2O2 coordination environment around the metal centre. The physicochemical properties and the spectroscopic features of [Pd(L)(OAc)] are consistent with its molecular structure. The complex was found to be an effective catalyst for the Suzuki–Miyaura cross‐coupling reactions of hydroxyaryl halides with arylboronic acids in predominantly aqueous media. The reactions afforded hydroxybiaryl products in good to excellent yields with a wide substrate scope.

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Efficient Palladium-catalyzed Suzuki–Miyaura reactions using phenolic Schiff base ligands under ambient conditions in aqueous media

Cited by 13 publications

References 33 publications

Hydrogenation and Redox Isomerization of Allylic Alcohols Catalyzed by a New Water-Soluble Pd–tetrahydrosalen Complex

Hydrogenation and Redox Isomerization of Allylic Alcohols Catalyzed by a New Water-Soluble Pd–tetrahydrosalen Complex

Selective Formation of Mononuclear Palladium and Acetonitrile-Bridged Dinuclear Palladium Complexes Containing a Chiral Tridentate Ligand

An acetatopalladium(II) complex with 1‐benzyl‐N‐(3,5‐di‐tert‐butylsalicylidene)piperidin‐4‐amine: Synthesis, structure and catalytic applications in Suzuki–Miyaura coupling of arylboronic acids with hydroxyaryl halides

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