Co-SAC catalyzed utilization of methanol and ethanol in the transfer hydrogenation of azo bonds: experimental and theoretical studies

文献信息

发布日期 2023-10-12
DOI 10.1039/D3GC02725B
影响因子 10.182
作者

Dibyajyoti Panja, Sadhan Dey, Rohini Saha, Rajib Sahu, Gourab Kanti Das, Preeti Bhobe, Sabuj Kundu


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摘要

Transfer hydrogenation (TH) of non-polar bonds using methanol and ethanol as hydrogen sources is a great challenge, and the development of an efficient 3d metal-based catalyst to accomplish such reactions is an exciting area to explore. Selective TH of amine surrogates to their corresponding primary amines using methanol or ethanol is difficult as mono/di-alkylated amines are produced as the major products. Notably, the TH of azo bonds to amines has not been reported yet. Herein, using Co-SAC, various azo compounds including commercially used dyes were effectively transfer hydrogenated to the corresponding primary amines, using ethanol and methanol as the hydrogen sources. Several control experiments were conducted to understand this catalytic process. Hammett studies revealed that transfer hydrogenation was more favorable with the substrates having electron-donating substituents. DFT calculations were performed to get a deeper insight into the mechanism, which disclosed that alcohol dehydrogenation and –NN– bond hydrogenation transpired through β-hydride elimination and Co-hydride insertion pathways, respectively.

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Green Chemistry

Green Chemistry
CiteScore: 16.1
自引率: 7.5%
年发文量: 944

Green Chemistry provides a unique forum for the publication of innovative research on the development of alternative green and sustainable technologies. The scope of Green Chemistry is based on, but not limited to, the definition proposed by Anastas and Warner (Green Chemistry: Theory and Practice, P T Anastas and J C Warner, Oxford University Press, Oxford, 1998). Green chemistry is the utilisation of a set of principles that reduces or eliminates the use or generation of hazardous substances in the design, manufacture and application of chemical products. Green Chemistry is at the frontiers of this continuously-evolving interdisciplinary science and publishes research that attempts to reduce the environmental impact of the chemical enterprise by developing a technology base that is inherently non-toxic to living things and the environment. Submissions on all aspects of research relating to the endeavour are welcome. The journal publishes original and significant cutting-edge research that is likely to be of wide general appeal. To be published, work must present a significant advance in green chemistry. Papers must contain a comparison with existing methods and demonstrate advantages over those methods before publication can be considered. For more information please see this Editorial. Coverage includes the following, but is not limited to: Design (e.g. biomimicry, design for degradation/recycling/reduced toxicity…) Reagents & Feedstocks (e.g. renewables, CO2, solvents, auxiliary agents, waste utilization…) Synthesis (e.g. organic, inorganic, synthetic biology…) Catalysis (e.g. homogeneous, heterogeneous, enzyme, whole cell…) Process (e.g. process design, intensification, separations, recycling, efficiency…) Energy (e.g. renewable energy, fuels, photovoltaics, fuel cells, energy storage, energy carriers…) Applications (e.g. electronics, dyes, consumer products, coatings, pharmaceuticals, preservatives, building materials, chemicals for industry/agriculture/mining…) Impact (e.g. safety, metrics, LCA, sustainability, (eco)toxicology…) Green chemistry is, by definition, a continuously-evolving frontier. Therefore, the inclusion of a particular material or technology does not, of itself, guarantee that a paper is suitable for the journal. To be suitable, the novel advance should have the potential for reduced environmental impact relative to the state of the art. Green Chemistry does not normally deal with research associated with 'end-of-pipe' or remediation issues.

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