Synthesis and Catalytic Properties of Cyclopalladated Complexes Bearing a Phosphane‐Sulfonate Ligand

Wang, Baiquan

doi:10.1002/ejic.201900805

Cited by 5 publications

(1 citation statement)

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“…These are adequate ligands for the synthesis of palladacycles. Palladacycles derived from N-donor ligands have been extensively studied in the last decade due to their properties and diverse applications [2], being one of the most used tools in organic synthesis [3], as catalysts in the Suzuki-Miyaura reaction [4]; in insertion reactions; or antiviral or antitumor applications.…”

Section: Introductionmentioning

confidence: 99%

Preparation and crystal structure of metallated 2,4,6-trimethylaniline imines

Diz-Gil

Bermúdez-Fernández

Munín‐Cruz

et al. 2020

Proceedings of the 24th International Electronic Conference on Synthetic Organic Chemistry

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In a typical condensation reaction, Schiff Base ligands were synthetized from 2,4,6trimethylaniline and the appropriate aldehydes. Treatment of the ligands with the corresponding palladium salt provided dinuclear cyclometallated compounds with bridging acetate moieties. The X-ray crystal structure analysis carried out was in agreement with the spectroscopic data. Herein we describe the preparation of the complexes; a brief discussion of the crystal structure is also given. The resulting dinuclear palladacycles are suitable for further ligand-exchange processes.

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Section: Introductionmentioning

confidence: 99%

Preparation and crystal structure of metallated 2,4,6-trimethylaniline imines

Diz-Gil

Bermúdez-Fernández

Munín‐Cruz

et al. 2020

Proceedings of the 24th International Electronic Conference on Synthetic Organic Chemistry

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Palladium‐Catalyzed C(sp³)−H Activation in A Monoterpene‐Based Compound Under Mild Conditions: A Combined Experimental and Theoretical Mechanistic Study

Kokina,

Shekhovtsov,

Tkachev

et al. 2024

ChemPlusChem

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The first example of the palladium‐catalyzed sp3 C‐H bond activation in a monoterpene‐based compound has been observed in the reaction of PdCl2 with a (+)‐3‐carene‐based ligand HL (HL = N‐((1aS,3S,7bR)‐1,1,3‐trimethyl‐7‐phenyl‐5‐(pyridin‐2‐yl)‐1a,2,3,7b‐tetrahydro‐1H‐cyclopropa[f]quinolin‐3‐yl)acetamide), which yielded the [PdLCl] complex. In contrast to the vast majority of C(sp3)‐H activation reactions which require prolonged heating and mixing due to the inert character of the corresponding bond, the reaction reported herein proceeds rapidly under mild conditions. A theoretical insight into the ligand deprotonation has been performed by DFT calculations. The mechanism of the C‐H activation involves (i) simultaneous coordination of the CH3 group of HL to the Pd2+ ion and decoordination of the Cl‐ anion with consequent formation of a Cl⋅⋅⋅H‐N hydrogen bond with the amide group, (ii) approximation of the out‐of‐sphere Cl‐ anion to one of the hydrogen atoms of the CH3 group mediated by the crane motion of the amide group and (iii) the ejection of the HCl molecule, which increases the entropy of the system and serves as a driving force for the reaction.

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Homo‐ and Copolymerization of Norbornene with Allyl Palladium and Nickel Complexes Bearing Imidazo[1,5‐a]pyridine Sulfonate Ligands

Yang

Wang

2021

Eur J Inorg Chem

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A series of allyl palladium and nickel complexes based on imidazo[1,5-a]pyridine sulfonate ligands were synthesized. All these complexes were fully characterized by 1 H and 13 C NMR, elemental analysis, and high-resolution mass spectrometry (HRMS). By treatment with Me 2 AlCl, palladium complexes showed high activities (up to 4.5 × 10 7 g of PNB (mol of Pd) À 1 h À 1 ) in norbornene polymerization, and the steric hindrance of the catalysts had little effect on the catalytic activities. They could also catalyze the copolymerization of norbornene with butyl vinyl ether (BVE) and ester monomers, but could not catalyze the copolymerization of norbornene with allyl butyl ether (ABE). In addition, the catalytic activities of nickel complexes for norbornene polymerization were similar to that of palladium complexes upon activation with MAO. They could catalyze copolymerization of norbornene with BVE and ABE, but not with ester monomers. In nickel system, the lower steric hindrance of the substituent led to higher activity.

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Synthesis and Catalytic Properties of Cyclopalladated Complexes Bearing a Phosphane‐Sulfonate Ligand

Cited by 5 publications

References 102 publications

Preparation and crystal structure of metallated 2,4,6-trimethylaniline imines

Preparation and crystal structure of metallated 2,4,6-trimethylaniline imines

Palladium‐Catalyzed C(sp³)−H Activation in A Monoterpene‐Based Compound Under Mild Conditions: A Combined Experimental and Theoretical Mechanistic Study

Homo‐ and Copolymerization of Norbornene with Allyl Palladium and Nickel Complexes Bearing Imidazo[1,5‐a]pyridine Sulfonate Ligands

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Synthesis and Catalytic Properties of Cyclopalladated Complexes Bearing a Phosphane‐Sulfonate Ligand

Cited by 5 publications

References 102 publications

Preparation and crystal structure of metallated 2,4,6-trimethylaniline imines

Preparation and crystal structure of metallated 2,4,6-trimethylaniline imines

Palladium‐Catalyzed C(sp3)−H Activation in A Monoterpene‐Based Compound Under Mild Conditions: A Combined Experimental and Theoretical Mechanistic Study

Homo‐ and Copolymerization of Norbornene with Allyl Palladium and Nickel Complexes Bearing Imidazo[1,5‐a]pyridine Sulfonate Ligands

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Palladium‐Catalyzed C(sp³)−H Activation in A Monoterpene‐Based Compound Under Mild Conditions: A Combined Experimental and Theoretical Mechanistic Study