Pd-NHC catalyzed Suzuki cross-coupling of benzyl ammonium salts

Zhong, Chuntao; Tang, Huiling; Cui, Benqiang; Shi, Yanhui; Cao, Changsheng

doi:10.1007/s11164-022-04795-6

Cited by 5 publications

(3 citation statements)

References 59 publications

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“…The peak at 6.54 ppm (f) is assigned to the hydrogen atom on the sulfonic acid group and is much smaller than the 7.12 ppm of BAC-2PTSA. [42,43] The difference can be explained that the increase in the proportion of PTSA in DES enhanced the strength of the hydrogen bond network, weakening the shielding effect on the hydrogen-bonded proton. So, the chemical shift moved to the low field, and the value of δ increased.…”

Section: Model Controlled By Internal Diffusionmentioning

confidence: 99%

Kinetics of polyvinyl butyral (PVB) synthesis reaction catalyzed by deep eutectic solvent

Luan

Zeng

et al. 2023

Can J Chem Eng

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In this work, the kinetics of the polyvinyl butyral (PVB) synthesis reaction catalyzed by the deep eutectic solvents (DESs) at the low‐temperature stage was studied to control the particle size of PVB resin and optimize its synthesis process. The effects of stirring speed, the concentration of polyvinyl alcohol (PVA), catalyst dosage, and temperature on the synthesis reaction of PVB were investigated. The data obtained from kinetic experiments at 283.15–298.15 K were fitted with the shrinking core models, and the results showed that the model controlled by internal diffusion fitted well with the experimental data. The internal diffusion coefficient, DA, of n‐butanal in the product layer was further calculated by the obtained model parameters, and it was applied to predict the synthesis reaction of PVB at different concentrations of n‐butanal. The results indicated that the shrinking core model controlled by internal diffusion is suitable to describe the kinetics of the PVB synthesis reaction. DES played a dual role in catalysis and dispersion in the synthesis of PVB, and it was a green catalyst with good potential for PVB industrial applications.

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Section: Model Controlled By Internal Diffusionmentioning

confidence: 99%

Kinetics of polyvinyl butyral (PVB) synthesis reaction catalyzed by deep eutectic solvent

Luan

Zeng

et al. 2023

Can J Chem Eng

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“…The unique structural features of H 8 -BINOL derivatives also cause them to self-assemble to form vesicles. The presence of aromatic rings in the compound ensures strong π-π interactions, which contribute to the formation of ordered structures [ 25 , 26 , 27 ]. Additionally, the H 8 -BINOL skeleton also provides ample hydrogen-bonding sites, further facilitating the self-assembly process.…”

Section: Introductionmentioning

confidence: 99%

The Intramolecular Charge Transfer Mechanism by Which Chiral Self-Assembled H8-BINOL Vesicles Enantioselectively Recognize Amino Alcohols

Wang,

Song,

Wei

et al. 2024

IJMS

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The chiral H8-BINOL derivatives R-1 and R-2 were efficiently synthesized via a Suzuki coupling reaction, and they can be used as novel dialdehyde fluorescent probes for the enantioselective recognition of R/S-2-amino-1-phenylethanol. In addition, R-1 is much more effective than R-2. Scanning electron microscope images and X-ray analyses show that R-1 can form supramolecular vesicles through the self-assembly effect of the π-π force and strong hydrogen bonding. As determined via analysis, the fluorescence of the probe was significantly enhanced by mixing a small amount of S-2-amino-1-phenylethanol into R-1, with a redshift of 38 nm, whereas no significant fluorescence response was observed in R-2-amino-1-phenylethanol. The enantioselective identification of S-2-amino-1-phenylethanol by the probe R-1 was further investigated through nuclear magnetic titration and fluorescence kinetic experiments and DFT calculations. The results showed that this mechanism was not only a simple reactive probe but also realized object recognition through an ICT mechanism. As the intramolecular hydrogen bond activated the carbonyl group on the probe R-1, the carbonyl carbon atom became positively charged. As a strong nucleophile, the amino group of S-2-amino-1-phenylethanol first transferred the amino electrons to a carbonyl carbocation, resulting in a significantly enhanced fluorescence of the probe R-1 and a 38 nm redshift. Similarly, S-2-amino-1-phenylethanol alone caused severe damage to the self-assembled vesicle structure of the probe molecule itself due to its spatial structure, which made R-1 highly enantioselective towards it.

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“…In continuation of our endeavors in exploring new methodologies in C–C cross-coupling reactions, herein, we describe the direct cross-coupling reaction of aryl methyl sulfides with the inexpensive and readily available electrophile, aryl bromides catalyzed by Ni(COD) 2 with BINAP as ligand and the aid of magnesium, producing the corresponding biaryls in moderate to good yields.…”

Section: Introductionmentioning

confidence: 99%

Nickel-Catalyzed Cross-Coupling Reaction of Aryl Methyl Sulfides with Aryl Bromides

Zhong,

Liu,

Qiu

et al. 2023

J. Org. Chem.

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Pd-NHC catalyzed Suzuki cross-coupling of benzyl ammonium salts

Cited by 5 publications

References 59 publications

Kinetics of polyvinyl butyral (PVB) synthesis reaction catalyzed by deep eutectic solvent

Kinetics of polyvinyl butyral (PVB) synthesis reaction catalyzed by deep eutectic solvent

The Intramolecular Charge Transfer Mechanism by Which Chiral Self-Assembled H8-BINOL Vesicles Enantioselectively Recognize Amino Alcohols

Nickel-Catalyzed Cross-Coupling Reaction of Aryl Methyl Sulfides with Aryl Bromides

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