Multidentate N-Heterocyclic Carbene Complexes of Nickel and Palladium: Structural Analysis and Catalytic Application in Mizoroki-Heck Coupling Reaction

2020 ◽  
Author(s):  
Li-Cheng Liu ◽  
Yan-Hsiang Tzeng ◽  
Cheng-Hau Hung ◽  
Hon Man Lee
Keyword(s):  
Structural Analysis ◽  
Coupling Reaction ◽  
Heck Coupling ◽  
Carbene Complexes ◽  
Catalytic Application

Trimetallic PEPPSI-Type Palladium N-Heterocyclic Carbene Complexes - Improved Catalyst Lifetime in the Mizoroki-Heck Coupling Reaction

2015 ◽  
Vol 2015 (24) ◽  
pp. 4076-4087 ◽  
Author(s):  
Francisco Martínez-Olid ◽  
Román Andrés ◽  
Juan C. Flores ◽  
Pilar Gómez-Sal
Keyword(s):  
Coupling Reaction ◽  
Heck Coupling ◽  
Carbene Complexes ◽  
Catalyst Lifetime

Poly(benzyl ether) Dendrimers Functionalized at the Core with Palladium Bis(N-Heterocyclic Carbene) Complexes as Catalysts for the Heck Coupling Reaction

2016 ◽  
Vol 55 (3) ◽  
pp. 1304-1314 ◽  
Author(s):  
Alba M. Ortiz ◽  
Alberto Sánchez-Méndez ◽  
Ernesto de Jesús ◽  
Juan C. Flores ◽  
Pilar Gómez-Sal ◽  
...  
Keyword(s):  
Coupling Reaction ◽  
Benzyl Ether ◽  
Heck Coupling ◽  
Carbene Complexes ◽  
The Core

The Synthesis and Catalytic Application of a New Class of Imprinted Silica

2003 ◽  
Vol 787 ◽  
Author(s):  
John D. Bass ◽  
Sandra L. Anderson ◽  
Alexander Katz
Keyword(s):  
Rational Design ◽  
Chemical Reactivity ◽  
Phenylboronic Acid ◽  
Coupling Reaction ◽  
Suzuki Coupling ◽  
Outer Sphere ◽  
Suzuki Coupling Reaction ◽  
New Class ◽  
Catalytic Application ◽  
Rate Acceleration

AbstractThe effect of chemical environment surrounding a synthetic heterogeneous catalyst active site is investigated using the hydrophilic imprinting of silica. Two model reaction systems have been used for this study: (i) Knoevenagel condensation of 3-nitrobenzaldehyde and malononitrile and (ii) Suzuki coupling of bromobenzene and phenylboronic acid. Using a catalyst in which isolated imprinted amines are surrounded by an acidic silanol-rich environment led to rate accelerations of over 120-fold relative to catalysts in which the amines are surrounded by a hydrophobic environment consisting of trimethylsilyl functional groups for system (i). This result parallels our previous study on the effect of the outer sphere composition on rate acceleration of Knoevenagel reactions using isophthalaldehyde as the aldehyde reactant. We also extended our method for the hydrophilic imprinting of bulk silica to organometallic systems, by successfully synthesizing a tethered palladium complex within the imprinted pocket. This material was used as an active catalyst for (ii). Our results show that a hydrophobic framework environment results in higher initial turnover frequencies than an acidic silanol-rich framework for the Suzuki coupling reaction of bromobenzene and phenylboronic acid, albeit with a lower overall effect than observed in the Knoevenagel system (i). Altogether, these results demonstrate the control of chemical reactivity via the rational design of the outer sphere using an imprinting approach.

Synthesis and Characterization of Novel PEPPSI type Pd–BICAAC Complexes

2022 ◽  
Author(s):  
Márton Nagyházi ◽  
Balázs Almási ◽  
Ádám Lukács ◽  
Attila Bényei ◽  
Tibor Nagy ◽  
...  
Keyword(s):  
High Activity ◽  
Coupling Reaction ◽  
Kinetic Studies ◽  
Elemental Mercury ◽  
Palladium Complexes ◽  
Synthesis And Characterization ◽  
Heck Coupling ◽  
Moisture Resistant

A series of bicyclic alkylamino carbenes (BICAAC) (where N-aryl = dipp, mes, 2,6-dimethyl-4-(dimethylamino)phenyl, 5a-d) and their novel air- and moisture-resistant pyridine (pyridine, 4 dimethylaminopyridine) containing palladium PEPPSI-type Pd(II) complexes (6a-e) were synthetized and characterized. The new palladium complexes have shown high activity in Mizoroki–Heck coupling reaction even at as low as 100 ppm loading (TON up to 10000). Kinetic studies revealed that reactions carried out in the presence of elemental mercury resulted in decrease in activity. It indicates that the coupling reaction may have both molecular and Pd(0)-mediated catalytic paths.

An expedient approach to enhance Mizoroki-Heck coupling reaction by infrared irradiation using palladacycle compounds

2015 ◽  
Vol 29 (8) ◽  
pp. 556-560 ◽  
Author(s):  
Fernando Ortega-Jiménez ◽  
Francisco X. Domínguez-Villa ◽  
Alfredo Rosas-Sánchez ◽  
Guillermo Penieres-Carrillo ◽  
José G. López-Cortés ◽  
...  
Keyword(s):  
Coupling Reaction ◽  
Heck Coupling ◽  
Infrared Irradiation
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