Green Chemistry最新文献

{"title":"Green solvent mixture for ultrasound-assisted solid-phase peptide synthesis: a fast and versatile method and its applications in flow and natural product synthesis","authors":"Jingyuan Liao, Renrong Zhang, Xuelei Jia, Meiling Wang, Chaoyi Li, Juntao Wang, Renjin Tang, Junrong Huang, Hengzhi You, Fen-Er Chen","doi":"10.1039/d4gc03864a","DOIUrl":"https://doi.org/10.1039/d4gc03864a","url":null,"abstract":"Peptides and depsipeptides play a significant role in diverse fields. Solid-phase peptide synthesis (SPPS) is the most renowned protocol for peptide production and can be coordinated with several process intensification techniques such as microwave, ultrasound, and continuous-flow. Until recently, most SPPS was carried out in <em>N</em>,<em>N</em>-dimethylformamide (DMF). However, the use of DMF has been restricted in the European Union since December 2023. Here we introduce a versatile <em>N</em>-formylmorpholine (NFM)/anisole (An) 1 : 1 solvent mixture that meets all green solvent criteria for SPPS. This innovation enables the first green ultrasound-assisted SPPS (US-GSPPS) and uses OxymaB to avoid hazardous benzotriazole-based compounds or OxymaPure coupling additives. Broad feasibility is demonstrated by successful synthesis of challenging peptides and natural products through on-resin esterification and solution/on-resin macrocyclization under ultrasound in NFM/An. Additionally, this mixture also functions as the first green solvent for continuous-flow solid-phase protocols.","PeriodicalId":78,"journal":{"name":"Green Chemistry","volume":null,"pages":null},"PeriodicalIF":9.8,"publicationDate":"2024-09-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142264446","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}

{"title":"Selective hydrogenation of guaiacol to 2-methoxycyclohexanone over supported Pd catalysts","authors":"Yota Taniwaki, Yoshinao Nakagawa, Mizuho Yabushita, Keiichi Tomishige","doi":"10.1039/d4gc03793f","DOIUrl":"https://doi.org/10.1039/d4gc03793f","url":null,"abstract":"Selective hydrogenation of guaiacol to 2-methoxycyclohexanone was investigated with various Pd catalysts. This reaction is much more difficult than the hydrogenation of phenol to cyclohexanone, namely in terms of the low reactivity of guaiacol and the reduced selectivity of 2-methoxycyclohexanone due to the demethoxylation reaction. Pd/TiO<small>₂</small> catalysts were found to be superior to other supported Pd catalysts in terms of activity and selectivity to 2-methoxycyclohexanone. The Pd dispersion did not affect the selectivity of Pd/TiO<small>₂</small> catalysts. Meanwhile, the increase of Pd dispersion decreased the turnover frequency, and the optimum Pd dispersion was about 25%. The presence of residual chloride ions had a negative effect on the selectivity to 2-methoxycyclohexanone. The optimal Pd/TiO<small>₂</small> catalyst gave 65% yield of 2-methoxycyclohexanone. The catalyst was reusable after washing with toluene solvent to extract residual organic species from the catalyst surface. The catalyst was capable of hydrogenating various phenolic compounds, namely methoxyphenols, into the corresponding cyclohexanone derivatives.","PeriodicalId":78,"journal":{"name":"Green Chemistry","volume":null,"pages":null},"PeriodicalIF":9.8,"publicationDate":"2024-09-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142264450","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}

{"title":"Metal- and oxidant-free carbonylation of benzylic and allylic C–H bonds with H2O via dual oxidative radical-polar crossover","authors":"Xiaona Yang, Bingjie Ren, Hongyu Guo, Rongfang Liu, Rong Zhou","doi":"10.1039/d4gc02381a","DOIUrl":"https://doi.org/10.1039/d4gc02381a","url":null,"abstract":"The selective and controllable functionalization of unreactive C(sp<small>³</small>)–H bonds under mild conditions is a highly desirable yet challenging goal in both organic synthesis and pharmaceutical industry. Herein, we report an unprecedented visible-light mediated metal- and oxidant-free carbonylation of both benzylic and allylic C–H bonds with H<small>₂</small>O. The synergistic combination of an organophotocatalyst 4CzIPN and a thiol enables the transformation of diverse arrays of benzylic and allylic C–H bonds into carbonyls in moderate to excellent yields with good functional group compatibility. Moreover, the oxidation of amines to aldehydes has also been realized by this protocol. Mechanistically, an oxidative radical-polar crossover (ORPC) process affords an alcohol intermediate, which then undergoes another ORPC process to furnish the carbonyl product.","PeriodicalId":78,"journal":{"name":"Green Chemistry","volume":null,"pages":null},"PeriodicalIF":9.8,"publicationDate":"2024-09-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142264448","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}

{"title":"De novo synthesis of 6-6-5 fused systems through electrochemical decarboxylation and radical domino additions","authors":"Chengcheng Yuan, Guanru Liu, Wenjing Guan, Jinlin Hang, Zheng Fang, Chengkou Liu, Kai Guo","doi":"10.1039/d4gc03260h","DOIUrl":"https://doi.org/10.1039/d4gc03260h","url":null,"abstract":"Highly complex fused systems are widely present in drug development. The direct electrosynthesis of fused systems through radical domino reactions features higher atom and step economy, using abundantly available starting materials and avoiding exogenous oxidants and reductants, and thus it has been in high demand and recognized as a green, powerful, and versatile synthetic tool but remains challenging because of the instability of the radical species under the electrolysis conditions and the inclusion of a quaternary ammonium salt. Herein, we developed a <em>de novo</em> electrosynthesis of 6-6-5 fused systems with two new rings constructed using a user-friendly undivided cell through decarboxylation and three-step radical addition under exogenous oxidant and quaternary ammonium salt free conditions. Excellent functional group, water and air compatibility was observed with good yields obtained.","PeriodicalId":78,"journal":{"name":"Green Chemistry","volume":null,"pages":null},"PeriodicalIF":9.8,"publicationDate":"2024-09-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142195727","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}

{"title":"The role of interactions between the cationic backbone and basic anions in green and ultra-selective catalytic synthesis of ethyl methyl carbonate in tunable ionized frameworks","authors":"Jie Chen, Jingjun Xie, Xiaoyan Chen, Rong Dong, Xue-Hui Ge, Ting Qiu","doi":"10.1039/d4gc02734e","DOIUrl":"https://doi.org/10.1039/d4gc02734e","url":null,"abstract":"The significance of renewable energy sources underscores the importance of developing efficient battery technologies. Ethyl methyl carbonate (EMC), with its superior performance as an electrolyte, is widely utilized in lithium-ion batteries. However, the production of EMC through green transesterification of dimethyl carbonate (DMC) with ethanol encounters challenges due to low EMC selectivity and catalyst reusability issues. In this study, we present the initial instance of utilizing an imidazole-based ionic framework, [CPIL-M]<small>_<em>n</em></small>[PhO], which exhibits an interaction between its cationic backbone and basic anions. This interaction is specifically designed to catalyse the selective transformation of basic anions with suitable Lewis basicity in the production of EMC <em>via</em> transesterification. The introduction of <em>N</em>,<em>N</em>′-carbonyldiimidazole into the ionic framework allows for tunable modulation of Lewis basicity on an electronic level, enhancing catalytic activity without compromising selectivity. These innovative designs enable [CPIL-M]<small>₄</small>[PhO] to exhibit remarkable performance, achieving 69.02% EMC yield and 90.19% selectivity, outperforming most reported catalysts. These findings could pave the way for the accelerated development of efficient catalysts for the sustainable production of EMC through transesterification methods in the future, thereby supporting the energy-efficient transition towards renewable energy sources.","PeriodicalId":78,"journal":{"name":"Green Chemistry","volume":null,"pages":null},"PeriodicalIF":9.8,"publicationDate":"2024-09-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142264630","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}

{"title":"Correction: An eco-friendly one-pot extraction process for curcumin and its bioenhancer, piperine, from edible plants in exosome-like nanovesicles","authors":"Meghana N. Kumar, Sreeram Peringattu Kalarikkal, Cathrine M. S. Bethi, Sukriti Narendra Singh, Janakiraman Narayanan and Gopinath M. Sundaram","doi":"10.1039/D4GC90098G","DOIUrl":"10.1039/D4GC90098G","url":null,"abstract":"<p >Correction for ‘An eco-friendly one-pot extraction process for curcumin and its bioenhancer, piperine, from edible plants in exosome-like nanovesicles’ by Meghana N. Kumar <em>et al.</em>, <em>Green Chem.</em>, 2023, <strong>25</strong>, 6472–6488, https://doi.org/10.1039/D3GC01287E.</p>","PeriodicalId":78,"journal":{"name":"Green Chemistry","volume":null,"pages":null},"PeriodicalIF":9.3,"publicationDate":"2024-09-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.rsc.org/en/content/articlepdf/2024/gc/d4gc90098g?page=search","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142195726","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}

{"title":"Preparation of methyl ethyl ketone from biomass-derived levulinic acid using a metal-free photocatalytic system and life cycle assessment study","authors":"Meng-Xiang Shen, Chen-Qiang Deng, Jie Yang, Jin Deng","doi":"10.1039/d4gc02798a","DOIUrl":"https://doi.org/10.1039/d4gc02798a","url":null,"abstract":"Levulinic acid (LA) is derived from lignocellulosic biomass and can undergo various chemical transformations to produce high-value chemicals. However, there are limited studies on C–C bond cleavage in LA. Methyl ethyl ketone (MEK) is a high-quality solvent with a wide range of industrial applications, traditionally produced from petroleum-derived <em>n</em>-butene. Here, we report a method for the production of MEK from LA using a metal-free photocatalytic system. Using acridine compounds as photosensitizers and thiophenols as hydrogen transfer reagents, high selectivity and yield of MEK are achieved under mild reaction conditions, and the reaction time is significantly shortened using a microchannel continuous flow photoreactor. Additionally, life cycle assessment indicates that this method has lower carbon emissions than other MEK production methods from LA. This catalytic system provides a green and efficient method to produce MEK from bio-based platform molecule LA, which meets the requirements of sustainable development.","PeriodicalId":78,"journal":{"name":"Green Chemistry","volume":null,"pages":null},"PeriodicalIF":9.8,"publicationDate":"2024-09-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142195687","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}

{"title":"Practical electrochemical hydrogenation of nitriles at the nickel foam cathode.","authors":"Rok Narobe, Marcel Nicolas Perner, María de Jesús Gálvez-Vázquez, Conrad Kuhwald, Martin Klein, Peter Broekmann, Sina Rösler, Bertram Cezanne, Siegfried R Waldvogel","doi":"10.1039/d4gc03446e","DOIUrl":"10.1039/d4gc03446e","url":null,"abstract":"<p><p>We report a scalable hydrogenation method for nitriles based on cost-effective materials in a very simple two-electrode setup under galvanostatic conditions. All components are commercially and readily available. The method is very easy to conduct and applicable to a variety of nitrile substrates, leading exclusively to primary amine products in yields of up to 89% using an easy work-up protocol. Importantly, this method is readily transferable from the milligram scale in batch-type screening cells to the multi-gram scale in a flow-type electrolyser. The transfer to flow electrolysis enabled us to achieve a notable 20 g day^-1 productivity of phenylethylamine at a geometric current density of 50 mA cm^-2 in a flow-type electrolyser with 48 cm² electrodes. It is noteworthy that this method is sustainable in terms of process safety and reusability of components.</p>","PeriodicalId":78,"journal":{"name":"Green Chemistry","volume":null,"pages":null},"PeriodicalIF":9.3,"publicationDate":"2024-09-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11413620/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142277410","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}

{"title":"anti-Dihydroxylation of olefins enabled by in situ generated peroxyacetic acid","authors":"Michael Tapera, Mohit Chotia, Jan Lukas Mayer-Figge, Adrián Gómez-Suárez, Stefan F. Kirsch","doi":"10.1039/d4gc03540b","DOIUrl":"https://doi.org/10.1039/d4gc03540b","url":null,"abstract":"Herein, we report a general and green protocol for the <em>anti</em>-dihydroxylation of unactivated alkenes. Combining H<small>₂</small>O<small>₂</small> and acetic acid at 50 °C results in the formation of peroxyacetic acid, which enables the efficient synthesis of a wide range of <em>anti</em> 1,2-diols in moderate to good yields without the need for hazardous solvents or expensive transition metals as catalysts.","PeriodicalId":78,"journal":{"name":"Green Chemistry","volume":null,"pages":null},"PeriodicalIF":9.8,"publicationDate":"2024-09-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142195725","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}

{"title":"3D structure-functional design of a biomass-derived photocatalyst for antimicrobial efficacy and chemical degradation under ambient conditions.","authors":"Wan Zhang, Yuanhao Liang, Cheng Hu, Weiwei Li, Jingru Lai, Kainan Chen, Sisi Xiang, Dariusz Niedzwiedzki, Jing Wu, Andrew Li, Susie Y Dai","doi":"10.1039/d4gc01246a","DOIUrl":"10.1039/d4gc01246a","url":null,"abstract":"<p><p>Surface sterilization and hazardous chemical degradation under ambient conditions can provide significant benefits for public and environmental health. Materials with sterilization and chemical degradation capacity under sunlight can efficiently reduce infectious disease incidence rates and toxic chemical exposure. Utilizing renewable energy for sustainable sterilization and degradation is more desirable as it reduces the potential secondary contamination. Herein, we report functional structure design using lignin, a renewable carbon heterogeneous polymer, to synthesize a highly efficient and stable photocatalyst that degrades environmentally hazardous organic compounds rapidly. Through a hydrolysis reaction between Ti-OH and the hydroxyl groups of lignin, Ti-O-C and Ti-O-Ti bonds were established and a lignin based photocatalyst with a hollow sphere structure (C_lignin@H-TiO₂) was formed. The presence of a homozygous carbon modified TiO₂ structure contributes to the enhanced photodegradation activity with solar light. The close hetero-interfacial contact between carbonized lignin and TiO₂ further improves the photocatalytic efficiency by facilitating effective charge carrier separation. After synthesis optimization, the resulting C_lignin@H-TiO₂ photocatalyst exhibits excellent performance in the degradation of atenolol under solar light irradiation with 100% degradation within five minutes. Additionally, it efficiently removes approximately 50% of PFOA and kills about 90% of bacteria within three hours. The uniform distribution of lignin within the crosslinking structures ensures a durable carbon modified TiO₂ framework, which remains stable after 10 cycles of usage. The robustness of the lignin-based photocatalyst enables incorporating the catalyst into diversified material formats and various usages. Coating of the photocatalyst onto device surfaces shows bacterial killing efficacy under sunlight. The photocatalysts based on lignin valorization present a green chemistry approach for environmental remediation and surface sterilization, which has long-term environmental protection benefits, with broad applications in toxin treatment and health protection against pathogen infection.</p>","PeriodicalId":78,"journal":{"name":"Green Chemistry","volume":null,"pages":null},"PeriodicalIF":9.3,"publicationDate":"2024-09-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11373602/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142152569","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}