Synthesis, characterization and low temperature self assembling of (η3-allyl)palladium complexes with 2-pyridyl-1,2,3-triazole bidentate ligands. Study of the catalytic activity in Suzuki–Miyaura reaction

Amadio, Emanuele; Scrivanti, Alberto; Chessa, Gavino; Matteoli, Ugo; Beghetto, Valentina; Bertoldini, Matteo; Rancan, Marzio; Dolmella, Alessandro; Venzo, Alfonso; Bertani, Roberta

doi:10.1016/j.jorganchem.2012.06.018

Cited by 24 publications

(9 citation statements)

References 63 publications

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“…The Pd II ions were coordinated by two chloride ions and two triazole N donors of the ligands, forming a six membered ring with a boat conformation. The Pd–N trz bond distances [2.013–2.032 Å] and the N trz –Pd–N trz bite angles [85.67(7) o and 87.10(7) o ] are within the expected ranges and comparable to previously reported structures of Pd‐triazolyl complexes ,–,. Interestingly, the crystal structures reveal no Pd⋅⋅⋅O interactions but there is a hydrogen bonding between the OH group on sp 3 C atom and the O atom of DMF with a contact distance of 1.901 Å and 1.930 Å, for 6 and 8 , respectively (Figure and ).…”

Section: Resultssupporting

confidence: 87%

Functionalized Bis(triazolyl)phenylmethanol–palladium(II) Catalysts for Cross Coupling Reactions in Water

et al. 2018

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PdII‐bis(triazolyl)phenylmethanol complexes bearing different groups (i. e., H, OMe, OH, COOH) directly attached to the benzyl rings were explored as precatalysts for copper‐free Sonogashira and Suzuki–Miyaura coupling reactions in water. Crystal structures reveal a bidentate N,N binding mode of the bis(triazolyl) ligands affording a distorted square planar PdII complexes. With the exception of the phenol‐substituted bis(triazolyl) ligands, the other three Pd complexes exhibited high activities toward Suzuki–Miyaura coupling reactions. Transmission electron microscopy (TEM) study and PPh3 poisoning experiments confirm that bis(triazoly)‐stabilized Pd nanoparticles (Pd NPs) were generated in situ during the catalytic reactions and involved as one of the active catalytic species in the Suzuki–Miyaura cross coupling.

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Section: Resultssupporting

confidence: 87%

Functionalized Bis(triazolyl)phenylmethanol–palladium(II) Catalysts for Cross Coupling Reactions in Water

et al. 2018

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“…Upon the formation of ligand, the δ value of C5 and C6 significantly shifted to higher values compared to their corresponding value in 3-butyn-1-ol. These data are good agreement with other triazole ligands [14,24,25,30].…”

Section: Characterization Of Ligand 1 By Nmr Spectroscopysupporting

confidence: 89%

Synthesis of a water-soluble thio-triazole ligand for biphase rhodium catalyzed hydroformylation of styrene

et al. 2020

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An environmentally safe water-soluble new ligand (2-(1-(2-(methylthio)ethyl)-1H-1,2,3-triazol-4-yl)ethanol) (ligand 1) has been synthesized by the click reaction between (2-azidoethyl)(methyl)sulfane and 3-butyn-1-ol. The structure of the novel ligand was confirmed by NMR spectroscopy. In situ combination of ligand 1 with [Rh(COD)Cl] 2 and [Rh (CO) 2 (acac)] (Rh: ligand = 1: 4) successfully employed for the biphasic catalytic hydroformylation of styrene. The formation of branched 2-phenylpropanol was confirmed by gas chromatogphic analysis. The recycled catalytic aqueous phase can be used three runs with remarkable catalytic efficiency.

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“…Using the synthetic pathway of Bertani et al . gave better results . Employing the ligands ( 1 a ‐ c ) and tetrakis(acetonitrile)copper(I) hexafluorophosphate ( CuP ) in a ratio of 1 to 1 the mono‐ligated copper(I) complexes 2 a – c could be obtained (for details see SI).…”

Section: Methodsmentioning

confidence: 99%

Click. Coordinate. Catalyze. Using CuAAC Click Ligands in Small‐Molecule Model Chemistry of Tyrosinase

et al. 2018

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Three triazolylmethylpyridine ligands are synthesized using the copper‐catalyzed azide‐alkyne cycloaddition (CuAAC). The corresponding copper(I) complexes are investigated as catalysts for the oxygenation of several monophenols, in analogy to the enzyme tyrosinase. Importantly, they show a higher catalytic activity than previously investigated systems. This is ascribed to the lower charge donation of the electron‐poor triazole heterocycle, supporting the hydroxylation of phenolic substrates by an electrophilic substitution mechanism.

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Synthesis, characterization and low temperature self assembling of (η3-allyl)palladium complexes with 2-pyridyl-1,2,3-triazole bidentate ligands. Study of the catalytic activity in Suzuki–Miyaura reaction

Cited by 24 publications

References 63 publications

Functionalized Bis(triazolyl)phenylmethanol–palladium(II) Catalysts for Cross Coupling Reactions in Water

Functionalized Bis(triazolyl)phenylmethanol–palladium(II) Catalysts for Cross Coupling Reactions in Water

Synthesis of a water-soluble thio-triazole ligand for biphase rhodium catalyzed hydroformylation of styrene

Click. Coordinate. Catalyze. Using CuAAC Click Ligands in Small‐Molecule Model Chemistry of Tyrosinase

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