Electrochemical synthesis of 1,2-diketones from alkynes under transition-metal-catalyst-free conditions

Zhou, Jie; Tao, Xiangzhang; Dai, Jianjun; Li, Chenguang; Xu, Jun; Xu, Hongmei; Xu, Hua‐Jian

doi:10.1039/c9cc03996a

Cited by 35 publications

(16 citation statements)

References 40 publications

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“…[304] Although, extensive works on the use of an electrochemical system for organic transformations are reported, none of them discussed the use of SACs, therefore several metal-free carbonbased organic electrosynthesis have been published. [305][306][307] The conventional ways of utilizing SACs for organic transformations have been used and summarized. [308] The use of SACs with electrochemical setup may further revolutionize the yield and better selectivity.…”

Section: Electrochemical Organic Transformationsmentioning

confidence: 99%

Single‐Atom Catalysts: A Sustainable Pathway for the Advanced Catalytic Applications

Singh

Sharma

Gaikwad

et al. 2021

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174

107

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In order to achieve these goals, it is of fundamental importance to design new catalysts that enable new benign routes to produce/ store and convert renewable energies and to obtain chemicals from waste. [3][4][5] We need to design new chemical pathways that replace traditional petrochemicalbased routes, considering new platform molecules, possibly derived by renewable resources such as agriculture/municipal wastes. This transition must fully involve the energy sector, with the entire redefinition of the pool of energy vectors for transportations, building heating systems, and power production. As the burning of fossil fuels and biomass are not anymore compatible with the dramatic increasing air pollution and global warming.To achieve all these targets, we will need to design nontoxic, earth-abundant, and less-expensive, highly efficient, and selective catalysts that can work under mild reaction conditions without producing significant waste. [6,7] Catalytic activity and selectivity are enabled via the many factors such as accessibility of active sites, interaction with the surface, i.e., varying support and coordinating sphere, composition of metals (bimetallic and many-metallic), size and shape; and chemical states of active sites which can to tailored via developing 2D catalyst [8][9][10] or via developing single atomic sites stabilized on hollow A heterogeneous catalyst is a backbone of modern sustainable green industries; and understanding the relationship between its structure and properties is the key for its advancement. Recently, many upscaling synthesis strategies for the development of a variety of respectable control atomically precise heterogeneous catalysts are reported and explored for various important applications in catalysis for energy and environmental remediation. Precise atomic-scale control of catalysts has allowed to significantly increase activity, selectivity, and in some cases stability. This approach has proved to be relevant in various energy and environmental related technologies such as fuel cell, chemical reactors for organic synthesis, and environmental remediation. Therefore, this review aims to critically analyze the recent progress on single-atom catalysts (SACs) application in oxygen reduction reaction, oxygen evolution reaction, hydrogen evolution reaction, and chemical and/or electrochemical organic transformations. Finally, opportunities that may open up in the future are summarized, along with suggesting new applications for possible exploitation of SACs.

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Section: Electrochemical Organic Transformationsmentioning

confidence: 99%

Single‐Atom Catalysts: A Sustainable Pathway for the Advanced Catalytic Applications

Singh

Sharma

Gaikwad

et al. 2021

Small

174

107

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“…In 2019, Dai, Xu and co‐workers presented an electrochemical method to obtain 1,2‐diketones by direct oxidation of internal alkynes under mild conditions and air atmospheres [47] . The synthetic strategy shows up as a green and efficient electrochemical method under catalyst free conditions, with inexpensive reagents and a wide substrate scope.…”

Section: Anodic Reactionsmentioning

confidence: 99%

“… Synthesis of 1,2‐diphenylethane‐1,2‐dione 45 a by direct oxidation of 1,2‐diphenylethyne 44 a under O 2 atmosphere [47] …”

Section: Anodic Reactionsmentioning

confidence: 99%

Alkynes as Building Blocks, Intermediates and Products in the Electrochemical Procedures Since 2000

et al. 2021

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Electrochemical procedures present a selective and environmentally friendly approach for fine chemicals preparation. The use of electricity instead of classical chemical reagents is economical and ecologically attractive. In fact, electricity from renewable resources can be used for electrochemical transformations with highly sustainable and desirable electrochemical applications. Alkynes triple C−C bond has a key role in many chemical transformations, and a growing attention has been recently paid to its electrochemical reactivity. The use of alkynes as building blocks or intermediates or products in electrochemical synthesis is presented in this minireview.

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“…Inspired by those work, we have developed a method for the synthesis of iso‐coumarin from o‐ (1‐alkynyl) benzoate and diorgano diselenide under electrochemical conditions. However, through previous studies, it was found that the reaction in batch yield can only reach 88 % at most, and there are also problems such as complicated operations, easy side reactions and long reaction time [13] . The literature investigation found that the electrochemical microreactor can solve these problems well, and it also has the advantages of small current gradient and effective use of electrical energy [14] .…”

Section: Introductionmentioning

confidence: 99%

Continuous Electrochemical Synthesis of Iso‐Coumarin Derivatives from o‐(1‐Alkynyl) Benzoates under Metal‐ and Oxidant‐Free

Lin

Fang

Zeng

et al. 2020

Chemistry A European J

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A non‐oxidant and metal‐free strategy for synthesizing iso‐coumarin by using a continuous electrochemical microreactor to initiate an oxidative cyclization reaction of o‐(1‐alkynyl) benzoate and radicals. This efficient and clean continuous electrosynthesis method not only avoids the complicated gas protection operation and production of by‐products in the batch processes, but also help to overcome the difficulty that batch metal catalysis and electrocatalysis are difficult to scale up, and has the potential for pilot‐scale experiment.

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Electrochemical synthesis of 1,2-diketones from alkynes under transition-metal-catalyst-free conditions

Abstract: A novel electrochemical protocol for the direct oxidation of internal alkynes in air to provide 1,2-diketones was developed.

Cited by 35 publications

References 40 publications

Single‐Atom Catalysts: A Sustainable Pathway for the Advanced Catalytic Applications

Single‐Atom Catalysts: A Sustainable Pathway for the Advanced Catalytic Applications

Alkynes as Building Blocks, Intermediates and Products in the Electrochemical Procedures Since 2000

Continuous Electrochemical Synthesis of Iso‐Coumarin Derivatives from o‐(1‐Alkynyl) Benzoates under Metal‐ and Oxidant‐Free

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