Green Chemistry最新文献

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CO2-Promoted photoredox-catalyzed hydrosulfonylation of alkenes with sulfinates†
IF 9.3 1区 化学
Green Chemistry Pub Date : 2025-01-30 DOI: 10.1039/d5gc00057b
Wanhui Huang , Ge Liu , Fangyuanhang Yang , Yuxi Ren , Yuzhen Gao , Weiping Su
{"title":"CO2-Promoted photoredox-catalyzed hydrosulfonylation of alkenes with sulfinates†","authors":"Wanhui Huang ,&nbsp;Ge Liu ,&nbsp;Fangyuanhang Yang ,&nbsp;Yuxi Ren ,&nbsp;Yuzhen Gao ,&nbsp;Weiping Su","doi":"10.1039/d5gc00057b","DOIUrl":"10.1039/d5gc00057b","url":null,"abstract":"<div><div>Herein, we report a CO<sub>2</sub>-promoted strategy for the photoredox-catalyzed hydrosulfonylation of alkenes with sulfinates under metal-, acid-, and exogenous reagent-free conditions. This method was compatible with a wide range of functional groups, including complex drug derivatives, making it a versatile and straightforward approach for synthesizing valuable sulfonyl compounds. Notably, CO<sub>2</sub>, which is an environmentally friendly additive, played an essential role in achieving the products, demonstrating a novel role of CO<sub>2</sub> in sulfonylation reactions.</div></div>","PeriodicalId":78,"journal":{"name":"Green Chemistry","volume":"27 14","pages":"Pages 3627-3633"},"PeriodicalIF":9.3,"publicationDate":"2025-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143740550","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Ice-confined synthesis of lecithin-protected perovskite microcrystals for stable optical synapses†
IF 9.3 1区 化学
Green Chemistry Pub Date : 2025-01-30 DOI: 10.1039/d4gc06568a
Zongyang Li , Yubo Peng , Jianlong Ji , Yuxuan Cheng , Jie Li , Ying Sun , Min Zhao , Xudong Jin , Huayun Du , Yuying Hao
{"title":"Ice-confined synthesis of lecithin-protected perovskite microcrystals for stable optical synapses†","authors":"Zongyang Li ,&nbsp;Yubo Peng ,&nbsp;Jianlong Ji ,&nbsp;Yuxuan Cheng ,&nbsp;Jie Li ,&nbsp;Ying Sun ,&nbsp;Min Zhao ,&nbsp;Xudong Jin ,&nbsp;Huayun Du ,&nbsp;Yuying Hao","doi":"10.1039/d4gc06568a","DOIUrl":"10.1039/d4gc06568a","url":null,"abstract":"<div><div>Perovskite microcrystals (PeMCs) show great potential for creating artificial optical synapses due to their low trap state density, high carrier mobility and high thermal stability. However, it is still a challenge to develop a green manufacturing process for preparing stable PeMCs. Here, we present a facile ice-confined strategy for achieving high-quality CsPbBr<sub>3</sub> PeMCs in pure water. In this method, lecithin protected PeMCs exhibited remarkable stability in polar solvents (water, ethanol, and acetone), which is due to the strong binding between lecithin and lead ions of PeMCs. Moreover, artificial optical synaptic transistors based on CsPbBr<sub>3</sub> PeMCs were successfully prepared. The devices successfully simulated visual functions by modeling important synaptic features such as excitatory postsynaptic currents, paired-pulse facilitation, spiking-rate-dependent plasticity, spiking-number-dependent plasticity and short-term memory to long-term memory transition. This work provides a new avenue for the synthesis of stable PeMCs and presents a new strategy for developing highly efficient artificial optical synaptic transistors.</div></div>","PeriodicalId":78,"journal":{"name":"Green Chemistry","volume":"27 14","pages":"Pages 3676-3683"},"PeriodicalIF":9.3,"publicationDate":"2025-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143740513","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Photoinduced transition metal-free borylation of aryl halides in an aqueous phase†
IF 9.3 1区 化学
Green Chemistry Pub Date : 2025-01-30 DOI: 10.1039/d5gc00495k
Mengqi Liu , Wan-Min Cheng , Zi-Long Li , Hong Jiang , Jimei Ma
{"title":"Photoinduced transition metal-free borylation of aryl halides in an aqueous phase†","authors":"Mengqi Liu ,&nbsp;Wan-Min Cheng ,&nbsp;Zi-Long Li ,&nbsp;Hong Jiang ,&nbsp;Jimei Ma","doi":"10.1039/d5gc00495k","DOIUrl":"10.1039/d5gc00495k","url":null,"abstract":"<div><div>A green photoinduced borylation of aryl halides catalyzed by 1-methylbenzimidazole in an aqueous phase is reported. The reaction proceeds efficiently under transition metal-free conditions at room temperature and is highlighted by operational simplicity, scalability, broad substrate compatibility, and good functional group tolerance, providing a practical and environmentally benign access to aryl boronic esters. Mechanistic experiments show that photoinduced homolytic cleavage of the activated diboron reagent constitutes a key step in this reaction.</div></div>","PeriodicalId":78,"journal":{"name":"Green Chemistry","volume":"27 14","pages":"Pages 3634-3639"},"PeriodicalIF":9.3,"publicationDate":"2025-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143740551","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Decarbonization approaches for ethylene production: comparative techno-economic and life-cycle analysis†
IF 9.3 1区 化学
Green Chemistry Pub Date : 2025-01-30 DOI: 10.1039/d4gc04538f
Woojae Shin , Bosong Lin , Haoxiang Lai , Gasim Ibrahim , Guiyan Zang
{"title":"Decarbonization approaches for ethylene production: comparative techno-economic and life-cycle analysis†","authors":"Woojae Shin ,&nbsp;Bosong Lin ,&nbsp;Haoxiang Lai ,&nbsp;Gasim Ibrahim ,&nbsp;Guiyan Zang","doi":"10.1039/d4gc04538f","DOIUrl":"10.1039/d4gc04538f","url":null,"abstract":"<div><div>Ethylene, a building block of the chemical industry, significantly contributes to global greenhouse gas (GHG) emissions, prompting interest in decarbonization approaches to align with recent carbon neutrality initiatives. This paper presents a comprehensive techno-economic analysis (TEA) and life cycle analysis (LCA) of GHG emissions, comparing conventional ethane-based ethylene plants with three decarbonization approaches. The study was conducted within the context of the U.S. average, with sensitivity analysis to identify key drivers affecting well-to-gate (WTG) GHG emissions and the levelized cost of ethylene (LCOE). The conventional plant exhibited a GHG emission of 869 kgCO<sub>2</sub>e per tonne-ethylene and a LCOE of $746 per tonne-ethylene. Substituting external natural gas fuels with grid or renewable electricity decreased the emissions to 806 and 717 kgCO<sub>2</sub>e per tonne-ethylene, respectively. The emissions of the grid-powered or renewable-powered electrically heated cracker that exports co-produced hydrogen to substitute conventional gray hydrogen were 1031 and −163 kgCO<sub>2</sub>e per tonne-ethylene, respectively. The application of CCS to purge gas showed 703 and 514 kgCO<sub>2</sub>e per tonne-ethylene emissions, respectively. The electric cracker showed lower emissions than the conventional plant below 380 kgCO<sub>2</sub>e per MW h electricity upstream, and at 60 kgCO<sub>2</sub>e per MW h, it achieved carbon neutrality. Regarding LCOE, when using a grid electricity source, no external natural gas, electric cracker, and adding CCS to purge gas showed $743, 833, and 771 per tonne-ethylene, respectively. When these plants adopt renewable electricity, their LCOEs will be $737, 746 and 757 per tonne-ethylene. Below $41.1 per MW h electricity price, the electric cracker had the lowest value among all cases. With hydrogen prices of $0.5–3.0 per kg-H<sub>2</sub>, the electric cracker's LCOE ranged from −$45(cost)–128(saving) per tonne-ethylene compared to the conventional concept.</div></div>","PeriodicalId":78,"journal":{"name":"Green Chemistry","volume":"27 14","pages":"Pages 3655-3675"},"PeriodicalIF":9.3,"publicationDate":"2025-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.rsc.org/en/content/articlepdf/2025/gc/d4gc04538f?page=search","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143740554","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
General and chemoselective reduction of phosphine oxides by an enhanced oxophilic competition mechanism†
IF 9.3 1区 化学
Green Chemistry Pub Date : 2025-01-30 DOI: 10.1039/d5gc00477b
Mengyao You , Ziwei Zhang , Chao Chen , Zhichao Mei , Xinxin Zhang , Jiang Bai , Haiyang Huang , Qiang Xiao
{"title":"General and chemoselective reduction of phosphine oxides by an enhanced oxophilic competition mechanism†","authors":"Mengyao You ,&nbsp;Ziwei Zhang ,&nbsp;Chao Chen ,&nbsp;Zhichao Mei ,&nbsp;Xinxin Zhang ,&nbsp;Jiang Bai ,&nbsp;Haiyang Huang ,&nbsp;Qiang Xiao","doi":"10.1039/d5gc00477b","DOIUrl":"10.1039/d5gc00477b","url":null,"abstract":"<div><div>Chemoselective reduction of phosphine oxides holds great significance for the preparation of phosphorus ligands and catalysts, as well as for the sustainable development of phosphorus chemistry. Previous approaches in this regard primarily involved the use of metal or custom-built catalysts, highly reactive and expensive reagents, or harsh conditions with deficient chemoselectivity. Here, we report an organocatalysis strategy for facile and efficient PO reduction, utilizing only commercially available catalysts and inexpensive, mild silanes under mild reaction conditions. This approach demonstrates excellent chemoselectivity for preserving various easily reduced groups. Computational studies elucidate that the enhanced oxophilicity of catalytically generated electron-deficient silane species is crucial. Furthermore, scale-up investigations highlight potential applications in industrial recycling of phosphine oxides and straightforward preparation of novel phosphorus ligands.</div></div>","PeriodicalId":78,"journal":{"name":"Green Chemistry","volume":"27 14","pages":"Pages 3743-3750"},"PeriodicalIF":9.3,"publicationDate":"2025-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143740555","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Cytoplasmic-peroxisomal spatial combination engineering in Candida tropicalis for enhanced terpenoid production†
IF 9.3 1区 化学
Green Chemistry Pub Date : 2025-01-30 DOI: 10.1039/d4gc06144f
Lihua Zhang , Cheng Fan , Haibing Zhang , Manzhi Zhu , Haiquan Yang , Yuanyuan Xia , Wei Shen , Xianzhong Chen
{"title":"Cytoplasmic-peroxisomal spatial combination engineering in Candida tropicalis for enhanced terpenoid production†","authors":"Lihua Zhang ,&nbsp;Cheng Fan ,&nbsp;Haibing Zhang ,&nbsp;Manzhi Zhu ,&nbsp;Haiquan Yang ,&nbsp;Yuanyuan Xia ,&nbsp;Wei Shen ,&nbsp;Xianzhong Chen","doi":"10.1039/d4gc06144f","DOIUrl":"10.1039/d4gc06144f","url":null,"abstract":"<div><div>Metabolic engineering of microorganisms for terpenoid biosynthesis is a green and sustainable alternative to plant extraction and chemical synthesis methods for producing plant-derived natural products. The compartmentalization of pathways or enzymes within organelles is increasingly recognized for its potential to eliminate metabolic crosstalk and enhance pathway efficacy in terpenoid production. However, the physicochemical environment of a given organelle may not meet the requirements for multiple enzymes. Here, a cytoplasmic-peroxisomal spatial-combination strategy was developed in <em>Candida tropicalis</em> to enhance terpenoid production. This strategy involved compartmentalizing the pathway from acetyl-CoA to mevalonate (MVA) within the cytoplasm and the subsequent steps from MVA to terpenoids within the peroxisome. Furthermore, we demonstrated that the pathway developed in this study is more effective because it provides optimal conditions for enzymes, and the use of the peroxisome membrane as a barrier to concentrate farnesyl diphosphate and geranylgeranyl pyrophosphate within the organelle. Additionally, we observed that this strategy efficiently enhanced productivity and was applicable to sesquiterpenoid, diterpene, and tetraterpenoid biosynthesis. Finally, under 5-L fed-batch fermentation, the titers of β-carotene and miltiradiene reached 9.9 g L<sup>−1</sup> and 4.2 g L<sup>−1</sup>, respectively. This study provides new insights into terpenoid biosynthesis in yeast.</div></div>","PeriodicalId":78,"journal":{"name":"Green Chemistry","volume":"27 14","pages":"Pages 3693-3705"},"PeriodicalIF":9.3,"publicationDate":"2025-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143740515","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Electrolyte pH modulation for efficient and durable electrochemical cement clinker precursor production†
IF 9.3 1区 化学
Green Chemistry Pub Date : 2025-01-30 DOI: 10.1039/d4gc06322h
Lei Xu , Lei Liu , Zheng Fang , Min Chen , Guangfeng Ou , Michio Suzuki , Yuya Sakai
{"title":"Electrolyte pH modulation for efficient and durable electrochemical cement clinker precursor production†","authors":"Lei Xu ,&nbsp;Lei Liu ,&nbsp;Zheng Fang ,&nbsp;Min Chen ,&nbsp;Guangfeng Ou ,&nbsp;Michio Suzuki ,&nbsp;Yuya Sakai","doi":"10.1039/d4gc06322h","DOIUrl":"10.1039/d4gc06322h","url":null,"abstract":"<div><div>Cement production is carbon intensive and accounts for 7–8% of global CO<sub>2</sub> emissions. Deep cement decarbonization can be achieved if limestone calcination is replaced with an ambient-temperature electrochemical process. A big challenge of this process is the significant deposition of the Ca(OH)<sub>2</sub> product on the membrane, causing unacceptable operational durability and energy efficiency. To address this issue, we designed a two-chamber membrane-based cement clinker precursor electrolyzer. The electrolyte pH modulation and its effect on decarbonization, precipitation, and cell voltage are investigated. We reveal a thin Ca(OH)<sub>2</sub> layer on the anode side of the membrane under fast decarbonization kinetics (99% current efficiency) at a pH of 5.1, increasing the cell voltage by 50%. A periodic pH change using intermittent stirring ensures a relatively constant voltage level with a sacrifice of ∼3% decarbonization efficiency. Membrane clogging is extremely significant in the cathode chamber due to the extreme pH environment (12.4), causing an inferior production rate of Ca(OH)<sub>2</sub> (59% of the theoretical limit). Introducing Ca<sup>2+</sup> into the catholyte leads to a much lower pH (11.8) and a clean membrane throughout the electrolysis, increasing the current efficiency for Ca(OH)<sub>2</sub> production to 84%. Our work demonstrates a viable approach for efficient and durable production of electrochemical cement clinker precursors.</div></div>","PeriodicalId":78,"journal":{"name":"Green Chemistry","volume":"27 14","pages":"Pages 3706-3714"},"PeriodicalIF":9.3,"publicationDate":"2025-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.rsc.org/en/content/articlepdf/2025/gc/d4gc06322h?page=search","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143740588","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Recent advances in ex ante techno-environmental-economic assessment of thermochemical waste or biomass to energy technologies based on process simulation†
IF 9.3 1区 化学
Green Chemistry Pub Date : 2025-01-30 DOI: 10.1039/D4GC06016D
Jiehong Tang, Yuting Tang, Hongyu Liu, Xinfei Chen, Xikui Zhang, Yin Chen, Shuang Liang, Junxuan Huang, Wen Teng, Ziwei Sun and Xiaoqian Ma
{"title":"Recent advances in ex ante techno-environmental-economic assessment of thermochemical waste or biomass to energy technologies based on process simulation†","authors":"Jiehong Tang, Yuting Tang, Hongyu Liu, Xinfei Chen, Xikui Zhang, Yin Chen, Shuang Liang, Junxuan Huang, Wen Teng, Ziwei Sun and Xiaoqian Ma","doi":"10.1039/D4GC06016D","DOIUrl":"https://doi.org/10.1039/D4GC06016D","url":null,"abstract":"<p >Thermochemical waste or biomass to energy (W/BtE) technology is known for its high conversion efficiency, rapid reaction rate, and foreseeable scale-up potential. To elucidate the coexisting risks and opportunities of newly proposed or ready-to-be-retrofitted W/BtE systems, ex ante techno-environmental-economic (TEE) assessment can provide multidimensional quantified guidance, while process simulation is an effective tool to predict their performance based on the existing laboratory- or pilot-scale experiment results. This review aims to provide a comprehensive understanding of process simulation-based TEE assessment of W/BtE systems. It summarizes the establishment of applicable conditions for reactor-level modelling approaches. Next, the calculation methods and principles for TEE assessment are introduced. Furthermore, based on the review of studies published from 2020 to 2024, it fully investigates the advances in the optimization of thermochemical processes through process simulation and the performance improvement of W/BtE systems, including waste or biomass to power (W/BtP) and to fuel (W/BtF) systems. Eventually, it highlights that the enhancement of data source quality and in-depth consideration of realistic conditions are the key aspects to be improved in the future.</p>","PeriodicalId":78,"journal":{"name":"Green Chemistry","volume":" 11","pages":" 2846-2899"},"PeriodicalIF":9.3,"publicationDate":"2025-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143580967","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
A mediator-free enzyme carbonaceous cathode for bioelectrocatalytic reduction of furfural to furfuryl alcohol†
IF 9.3 1区 化学
Green Chemistry Pub Date : 2025-01-30 DOI: 10.1039/d5gc00168d
Shize Zheng , Chenxi Zhang , Peng Zhan , Xiangshi Liu , Houchao Shan , Yong Wang , Bin Wang , Peiyong Qin , Di Cai , Tianwei Tan
{"title":"A mediator-free enzyme carbonaceous cathode for bioelectrocatalytic reduction of furfural to furfuryl alcohol†","authors":"Shize Zheng ,&nbsp;Chenxi Zhang ,&nbsp;Peng Zhan ,&nbsp;Xiangshi Liu ,&nbsp;Houchao Shan ,&nbsp;Yong Wang ,&nbsp;Bin Wang ,&nbsp;Peiyong Qin ,&nbsp;Di Cai ,&nbsp;Tianwei Tan","doi":"10.1039/d5gc00168d","DOIUrl":"10.1039/d5gc00168d","url":null,"abstract":"<div><div>The valorisation of biomass derivatives into fine chemicals through the combination of electro-enzymatic catalysis under green chemistry principles holds promising potential. However, bottlenecks, including poor electron transfer efficiency between the electrode surface and electron mediators, inefficient cofactor regeneration, and the high cost of enzymes and electron mediators, continue to hinder practical applications. Herein, to address the abovementioned technical barriers, we proposed an electron mediator-free bioelectrocatalytic system that integrated electrochemical NADH regeneration and enzymatic reactions. The proposed system was based on a novel, orderly assembled composite bioelectrode composed of a conjugated structure of covalent organic frameworks (COFs, namely, TpBD), which encapsulated cofactor-dependent oxidoreductases. The as-prepared composite bioelectrode was further applied to the highly selective hydrogenation of furfural to furfuryl alcohol. Results indicated that the electron pathway involved in the TpBD conjugated structure guaranteed effective cofactor regeneration on the composite bioelectrode without the assistance of costly electron mediators, thereby promoting the enzymatic reduction of furfural. A high furfural conversion of 98.94% was realized, accompanied by remarkable furfuryl alcohol selectivity of 90.13% at −1.4 V (<em>vs.</em> Ag/AgCl). The novel composite bioelectrode also showed good stability and reusability. Up to 88.1% of the original furfuryl alcohol selectivity was preserved after 10 cycles of recycling. This work presents a promising green alternative route for the valorisation of furfural, with great potential for extending to the valorization of other renewable biomass derivatives.</div></div>","PeriodicalId":78,"journal":{"name":"Green Chemistry","volume":"27 14","pages":"Pages 3733-3742"},"PeriodicalIF":9.3,"publicationDate":"2025-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143740591","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Site-selective electrochemical synthesis of nitrogen-enriched bis-pyrazole derivatives: a sustainable approach for N–N versus NN bond formation†
IF 9.3 1区 化学
Green Chemistry Pub Date : 2025-01-30 DOI: 10.1039/d4gc06597b
Lei Liu , Wengzhe Huang , Ye Yuan , Lu Lu , Yongxing Tang , Wei Huang
{"title":"Site-selective electrochemical synthesis of nitrogen-enriched bis-pyrazole derivatives: a sustainable approach for N–N versus NN bond formation†","authors":"Lei Liu ,&nbsp;Wengzhe Huang ,&nbsp;Ye Yuan ,&nbsp;Lu Lu ,&nbsp;Yongxing Tang ,&nbsp;Wei Huang","doi":"10.1039/d4gc06597b","DOIUrl":"10.1039/d4gc06597b","url":null,"abstract":"<div><div>Two bis-pyrazole derivatives with azo (NN) and dinitrogen (N–N) linkages were synthesized through an electrochemical homo-coupling process, starting from 3,5-diamino-4-cyanopyrazole. Through systematic optimization of electrochemical conditions and electrolytes, we achieved site-selective coupling at the amino or pyrazole nitrogen sites, yielding azopyrazole derivative and N–N homo-coupling product . This selective synthesis resulted in high yields of up to 86% for NN bond formation and 78% for N–N bond formation. Cyclic voltammetry studies and radical trapping experiments revealed the critical involvement of amino radicals in the coupling reactions, providing new mechanistic insights. The nitration product of the azo-pyrazole compound exhibits promising detonation properties. This research not only expands the scope of electrochemical synthesis techniques but also offers valuable insights into the reactivity of diverse nitrogen centers within aminopyrazole frameworks. This method presents a potential strategy to enhance the efficiency of synthesizing nitrogen-rich heterocyclic molecules, which are essential in various industrial and technological applications.</div></div>","PeriodicalId":78,"journal":{"name":"Green Chemistry","volume":"27 14","pages":"Pages 3727-3732"},"PeriodicalIF":9.3,"publicationDate":"2025-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143740590","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
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