Zinc‐Catalyzed Hydroamination Reactions

Li, Tianshu; Wiecko, Jelena; Roesky, Peter W.

doi:10.1002/9783527675944.ch5

Cited by 9 publications

(7 citation statements)

References 100 publications

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“…This reaction, while typically thermodynamically feasible, shows high kinetic barriers when it is uncatalyzed, due to the requirement of two electron-rich components to react with each other . Progress has been made with the employment of d- and f-block metal catalysts that can be divided into two categories (Figure a): group 4 and lanthanide catalysts (type I), which are highly active but typically lack functional group tolerance, and the group 9–12 precious-metal-containing catalysts (type II), ,, which show the opposite properties. Therefore, there is still a need to develop catalysts that combine the advantages of both types of catalysts.…”

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confidence: 99%

Alkyne Hydroamination Catalyzed by Silica-Supported Isolated Zn(II) Sites

Cook

Copéret

2018

Organometallics

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Hydroamination is an atom-economical reaction to form C–N bonds, which are ubiquitous in organic compounds. Hydroamination has seen prolific advancements and has mostly focused on the development of homogeneous catalysts based on lanthanides or transition metals. Here, we have developed silica-supported, site-isolated Zn(II) sites through a combined surface organometallic chemistry (SOMC) and thermolytic molecular precursor (TMP) approach and show that they catalyze the intramolecular hydroamination of alkynes. This material is applicable to a broad range of substrates. On the basis of kinetics and in situ IR spectroscopic studies, we propose that the mechanism involves coordination of the aminoalkyne onto Zn(II) followed by the heterolytic activation of the N–H bond and subsequent cyclization and proton transfer.

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confidence: 99%

Alkyne Hydroamination Catalyzed by Silica-Supported Isolated Zn(II) Sites

Cook

Copéret

2018

Organometallics

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“…Various research groups have studied the potential of zinc in catalysis for hydroamination reactions [184,185]. The first examples of alkene cyclohydroamination catalyzed…”

Section: Hydroaminationmentioning

confidence: 99%

“…Various research groups have studied the potential of zinc in catalysis for hydroamination reactions [184,185] [186]. Several modulations of the steric and electronic properties of the aminotroponimate skeleton were further attempted to improve the catalyst activity and stability [180,187,188].…”

Section: Hydroaminationmentioning

confidence: 99%

Earth-Abundant 3d Transition Metal Catalysts for Hydroalkoxylation and Hydroamination of Unactivated Alkenes

et al. 2021

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“…Over recent years, in the developing trend towards greener, more sustainable chemistry, zinc catalysis has become increasingly popular [ 15 , 16 ]. Metals with great potency and environmental viability are most often used as catalysts.…”

Section: Introductionmentioning

confidence: 99%

Bio-Based (Chitosan-ZnO) Nanocomposite: Synthesis, Characterization, and Its Use as Recyclable, Ecofriendly Biocatalyst for Synthesis of Thiazoles Tethered Azo Groups

et al. 2022

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In recent years, nanotechnology has become a considerable research interest in the area of preparation of nanocatalysts based on naturally occurring polysaccharides. Chitosan (CS), as a naturally occurring biodegradable and biocompatible polysaccharide, is successfully utilized as an ideal template for the immobilization of metal oxide nanoparticles. In this study, zinc oxide nanoparticles have been doped within a chitosan matrix at dissimilar weight percentages (5, 10, 15, 20, and 25 wt.% CS/ZnO) and have been fabricated by using a simple solution casting method. The prepared solutions of the nanocomposites were cast in a Petri-dish and were subsequently shaped as a thin film. After that, the structural features of the nanocomposite film have been studied by measuring the FTIR, SEM, and XRD analytical tools. FTIR spectra showed the presence of some changes in the major characteristic peaks of chitosan due to interaction with ZnO nanoparticles. In addition, SEM graphs exhibited dramatic morphology changes on the chitosan surface, which is attributed to the surface adsorption of ZnO molecules. Based on the results of the investigated organic catalytic reactions, the prepared CS/ZnO nanocomposite film (20 wt.%) could be a viable an effective, recyclable, and heterogeneous base catalyst in the synthesis of thiazoles. The results showed that the nanocomposite film is chemically stable and can be collected and reused in the investigated catalytic reactions more than three times without loss of its catalytic activity.

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Zinc‐Catalyzed Hydroamination Reactions

Cited by 9 publications

References 100 publications

Alkyne Hydroamination Catalyzed by Silica-Supported Isolated Zn(II) Sites

Alkyne Hydroamination Catalyzed by Silica-Supported Isolated Zn(II) Sites

Earth-Abundant 3d Transition Metal Catalysts for Hydroalkoxylation and Hydroamination of Unactivated Alkenes

Bio-Based (Chitosan-ZnO) Nanocomposite: Synthesis, Characterization, and Its Use as Recyclable, Ecofriendly Biocatalyst for Synthesis of Thiazoles Tethered Azo Groups

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