Zhenguo Zhang , Mi Ren , Ming-Zhu Lu , Zhenhua Jia , Teck-Peng Loh
{"title":"Carbonyl group-assisted 1,3-amine addition to α,β-unsaturated aldehydes","authors":"Zhenguo Zhang , Mi Ren , Ming-Zhu Lu , Zhenhua Jia , Teck-Peng Loh","doi":"10.1016/j.gresc.2024.04.003","DOIUrl":"10.1016/j.gresc.2024.04.003","url":null,"abstract":"<div><div>An unusual 1,3-addition products were obtained when amines were reacted with α,β-unsaturated aldehydes compounds in the presence of iodine and an oxidant. The versatile unsaturated α-amino acetals are highly useful amino acid derivatives and can be converted to a wide variety of synthetically useful building blocks. Various control experiments have shown that the reaction proceeded via a mechanism involving the formation of imine/enamine intermediates followed by a 1,2-amine group migration reaction.</div></div>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"6 2","pages":"Pages 202-205"},"PeriodicalIF":0.0,"publicationDate":"2025-05-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141936667","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Shadeera Rouf , Yaser E. Greish , Bart Van der Bruggen , Sulaiman Al-Zuhair
{"title":"Enhancement of CO2 hydrogenation to formate using formate dehydrogenase immobilized on UiO66 and its derivatives","authors":"Shadeera Rouf , Yaser E. Greish , Bart Van der Bruggen , Sulaiman Al-Zuhair","doi":"10.1016/j.gresc.2024.09.005","DOIUrl":"10.1016/j.gresc.2024.09.005","url":null,"abstract":"<div><div>In the present work, a highly stable zirconium-based metal-organic framework (MOF), UiO66, and its derivative, UiO66-NH<sub>2</sub>, were tested as support materials to immobilize Formate dehydrogenase (FDH) for use in CO<sub>2</sub> hydrogenation. Both physical adsorption and cross-linking approaches were tested for immobilization. Cross-linking with glutaraldehyde has been suggested to enhance the stability of the enzyme and reduce leaching, which is prone to physical attachment. The adsorption isotherm and kinetics were best described by Sips and pseudo-second-order models, respectively. The influences of the secondary structure of the protein on catalytic performance and formate production were studied. Immobilization of FDH resulted in a change in the secondary structure, with the α-helical content increased from 29.4 % of the free enzyme to 43 % after immobilization on UiO66 and 100 % after immobilization on UiO66-NH<sub>2</sub>. This structural change significantly enhanced the enzyme activity. At optimum conditions of pH 5.5 and 30 mM NaHCO<sub>3</sub>, the activity of immobilized FDH was 19.6 times higher than that of free FDH. Formate production was also enhanced using immobilized FDH on UiO66-NH<sub>2</sub>, where production was 2.4 times higher than that achieved using free FDH. Better stability and reusability were achieved by cross-linking with glutaraldehyde. The results of this work provide a novel insight into the changes in the secondary structure of FDH after immobilization and its positive effect on catalytic efficiency. These findings are expected to pave the way for the commercial applications of FDH for CO<sub>2</sub> utilization.</div></div>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"6 2","pages":"Pages 140-156"},"PeriodicalIF":0.0,"publicationDate":"2025-05-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144535920","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Tao Ye , Na Lin , Jia-Huan Shen , Lichun Kong , Yang-Zi Liu , Quannan Wang , Wei-Ping Deng
{"title":"Ferric nitrate-catalyzed aerobic oxidative ring-opening of substituted furans for the stereoselective synthesis of (Z)-1,4-enediones","authors":"Tao Ye , Na Lin , Jia-Huan Shen , Lichun Kong , Yang-Zi Liu , Quannan Wang , Wei-Ping Deng","doi":"10.1016/j.gresc.2023.11.007","DOIUrl":"10.1016/j.gresc.2023.11.007","url":null,"abstract":"<div><div>A simple and highly efficient catalytic system for the selective aerobic oxidative ring-opening of substituted furans has been achieved using Fe(NO<sub>3</sub>)<sub>3</sub><strong>·</strong>9H<sub>2</sub>O as a catalyst and air as an oxidant under mild conditions. A series of (<em>Z</em>)-1,4-enediones were obtained in good yields (up to 97 %) with excellent stereoselectivity (up to > 20:1 <em>Z</em>/<em>E</em> ratio). The present synthetic method exhibits perfect atom economy, wide substrate scope, and highly functionalized products allowing diverse transformations.</div></div>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"6 2","pages":"Pages 179-182"},"PeriodicalIF":0.0,"publicationDate":"2025-05-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138512319","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Muhammad Zubair Mohsin , Ali Mohsin , Waqas Qamar Zaman , Xiaojuan Zhu , Xihua Zhao , Zain Abbas , Muhammad Hammad Hussain , Ali Shan , Salim-ur-Rehman , Muhammad Asif Nawaz , Rabia Omer , Yingping Zhuang , Meijin Guo , Jiaofang Huang
{"title":"Efficient toluene degradation using Bacillus subtilis biofilm-supported Mn–Ce/zeolite catalysts","authors":"Muhammad Zubair Mohsin , Ali Mohsin , Waqas Qamar Zaman , Xiaojuan Zhu , Xihua Zhao , Zain Abbas , Muhammad Hammad Hussain , Ali Shan , Salim-ur-Rehman , Muhammad Asif Nawaz , Rabia Omer , Yingping Zhuang , Meijin Guo , Jiaofang Huang","doi":"10.1016/j.gresc.2024.01.006","DOIUrl":"10.1016/j.gresc.2024.01.006","url":null,"abstract":"<div><div>This study investigated a new approach for synthesizing <em>Bacillus subtilis</em> biofilm-supported Mn–Ce/zeolite catalysts for the degradation of gaseous toluene. Four different metal oxide nano-catalysts (ZMn, ZMnCe-10 %, ZMnCe-20 %, and ZMnCe-30 %) were synthesized with varying ratios of manganese (Mn) and cerium (Ce) on zeolite nanoparticles. TEM, SEM, XRD, BET, XPS, and EDX mapping were used to examine these four samples, as well as simple zeolite. Based on these analyses, the catalytic activity of the prepared samples ZMn, ZMnCe-10 %, ZMnCe-20 %, and ZMnCe-30 % for the complete oxidation of toluene and toluene intermediate products were tested with Non-thermal plasma (NTP) technology in a dielectric barrier discharge (DBD) reactor. Among all, ZMnCe-20 % showed the highest toluene degradation efficiency (89 %) at low concentrations (200 ppm) and humidity (>50 %). Later, highly efficient and hydrophobic nano-biocatalysts were prepared by combining <em>B. subtilis</em> biofilm wild-type (WT) and engineered <em>B. subtilis</em> biofilm EPS with ZMnCe-20 % catalyst. EPS is the main component found in biofilm matrix and plays a key role in influencing properties such as biofilm stability, electron transfer, surface roughness and hydrophobicity. Compared to WT <em>B. subtilis</em> biofilm, EPS overexpressed <em>B. subtilis</em> biofilm showed stronger growth and development on ZMnCe-20 % nanocatalyst. Moreover, the NTP system packed with ZMnCe-20 %/biofilm (EPS+) nano-biocatalyst exhibited the highest toluene degradation activity (99 %) with (83 %) CO<sub>2</sub> selectivity, (up to 50 %) reduction in NOx concentration and complete ozone decomposition at (250 ppm) toluene concentrations and increased humidity (>90 %). High-energy electrons generated in the NTP system break the C–H and C–C bond between the rings of the toluene molecule, forming several byproducts which are later reacted with active radical species such as O<img>, OH<img>, and O<sub>3</sub> and further converted into final degradation products (CO<sub>2</sub> and H<sub>2</sub>O). The results demonstrated successful biofilm development and growth on the ZMnCe-20 % catalyst with advanced features such as superhydrophobicity, H<sub>2</sub>O resistance, improved surface roughness, and electron generation. In short, the study's approach combines bioengineering and material science to develop sustainable nano-biocatalysts for removing VOCs in industrial and environmental settings.</div></div>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"6 2","pages":"Pages 128-139"},"PeriodicalIF":0.0,"publicationDate":"2025-05-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139772287","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Electrochemical cascade pyrazole annulation and C-H halogenation for the synthesis of 4-halopyrazoles","authors":"Haijin Guo , Yunyun Liu , Jie-Ping Wan","doi":"10.1016/j.gresc.2023.10.004","DOIUrl":"10.1016/j.gresc.2023.10.004","url":null,"abstract":"<div><div>The synthesis of 4-halo-functionalized pyrazoles by electrochemical cascade reactions between <em>N,N</em>-dimethyl enaminones and proper hydrazine reagents in the presence of a halogen source is realized at room temperature. The work provides tunable and efficient accesses to 4-chloro- and 4-bromopyrazoles in aqueous THF (tetrahydrofuran) without using any transition metal reagent.</div></div>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"6 2","pages":"Pages 206-210"},"PeriodicalIF":0.0,"publicationDate":"2025-05-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"136056841","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Electrochemical N-olefination for the regio- and stereo-selective synthesis of vinyl azoles","authors":"Kejun Lin , Jianyong Lan , Lin Hao , Tingshun Zhu","doi":"10.1016/j.gresc.2024.01.005","DOIUrl":"10.1016/j.gresc.2024.01.005","url":null,"abstract":"<div><div>A selenium-catalyzed electrosynthesis involving regio- and stereo-selective <em>N</em>-olefination of azoles was developed. The room-temperature reaction was efficient (up to 97 % yield) and compatible with various styrenes and azoles. Mechanistic study showed that the cascade reaction was triggered by the selenium-cation-mediated electrophilic <em>trans-</em>aminoselenation, and followed by an oxidative <em>cis</em>-elimination of selane. The electrosynthesis was also well compatible with the more challenging internal alkene substrates, giving the desired <em>N</em>-vinyl azoles in up to 88 % yield and > 20:1 <em>Z/E</em> ratio.</div></div>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"6 2","pages":"Pages 183-186"},"PeriodicalIF":0.0,"publicationDate":"2025-05-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139463206","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Xin-Yue Niu , Chao-Yang Li , Cong-Cong Zhang , Zhan-Wei Bu , Yan Xie , Wen-Jing Zhang , Qi-Lin Wang
{"title":"Water-controlled skeletal editing or peripheral modification of ortho-chalcone-substituted organophosphines","authors":"Xin-Yue Niu , Chao-Yang Li , Cong-Cong Zhang , Zhan-Wei Bu , Yan Xie , Wen-Jing Zhang , Qi-Lin Wang","doi":"10.1016/j.gresc.2023.12.003","DOIUrl":"10.1016/j.gresc.2023.12.003","url":null,"abstract":"<div><div>Skeletal editing of organophosphines is highly challenging owing to the high P-C bond dissociation energy. Herein, we report an efficient catalyst- and additive-free skeletal editing strategy to transform easily accessible <em>ortho</em>-chalcone based organophosphines into new and complex phosphine oxides, that are unattainable by conventional methods. Water is indispensable to this transformation and serves as the oxygen source to cleave P-C bonds. Interestingly, it is possible to achieve the peripheral modification of organophosphines into phosphonium salts in the absence of water. This water-controlled skeletal editing or peripheral modification strategy is embedded with the merits of high bond- and ring-forming efficiency and complete regio-, chemo- and stereoselectivity.</div></div>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"6 2","pages":"Pages 157-163"},"PeriodicalIF":0.0,"publicationDate":"2025-05-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139104614","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Zheng-Wei Wu , Han-Han Kong , Yong Wei , Wen-Chao Zhou , Long Wang , Liang-Qiu Lu , Qing-Qing Yang
{"title":"Photoinduced radical cascade brominative addition/spirocyclization of N-arylpropiolamides and CBr4 with O2 as oxidant","authors":"Zheng-Wei Wu , Han-Han Kong , Yong Wei , Wen-Chao Zhou , Long Wang , Liang-Qiu Lu , Qing-Qing Yang","doi":"10.1016/j.gresc.2024.01.004","DOIUrl":"10.1016/j.gresc.2024.01.004","url":null,"abstract":"<div><div>A visible-light-induced brominated spirocyclization of <em>N</em>-arylpropiolamides and CBr<sub>4</sub> for the synthesis of 3-bromo-azaspiro[4,5]trienones is reported here. This process allows the formation of C–Br, C–C, and C=O bonds in a single reaction <em>via</em> a cascade radical addition/<em>ipso</em>-cyclization/oxidative dearomatization sequence. This protocol also features high functional group tolerance, operational simplicity and the use of molecular oxygen as an oxidant as well as sustainable photocatalyst- and additive-free reaction conditions at room temperature. Meanwhile, the presented straightforward and sustainable strategy has also been applied to the synthesis of several biologically active compounds.</div></div>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"6 2","pages":"Pages 187-191"},"PeriodicalIF":0.0,"publicationDate":"2025-05-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139471196","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Yuanyun Gu , Yaxin Feng , Baotong Huang , Yan-En Wang , Yaqi Yuan , Dan Xiong , Yonghong Hu , Xiufang Xu , Patrick J. Walsh , Jianyou Mao
{"title":"Rapid access to diverse indoles by addition/SNAr with Grignard reagents and 2-fluorophenyl acetonitriles","authors":"Yuanyun Gu , Yaxin Feng , Baotong Huang , Yan-En Wang , Yaqi Yuan , Dan Xiong , Yonghong Hu , Xiufang Xu , Patrick J. Walsh , Jianyou Mao","doi":"10.1016/j.gresc.2024.02.004","DOIUrl":"10.1016/j.gresc.2024.02.004","url":null,"abstract":"<div><div>Indoles are essential heterocycles in natural products, biological chemistry, and medicinal chemistry. Efficient approaches to their synthesis, therefore, remain in demand. Herein is reported a novel and scalable method to produce a wide variety of indoles by combining Grignard reagents and 2-fluorobenzyl cyanides (59 examples, 45 %–95 % yields). The Grignard reagent adds to the nitrile to give a metalated imine that undergoes S<sub>N</sub>Ar with unactivated C–F bonds. This strategy installs the R group of RMgX at the indole 2-position, and it is noteworthy that a diverse array of Grignard reagents (aryl, alkyl, vinyl, and cyclopropyl) provide the desired heterocyclic products. The resulting <em>N</em>-magnesiated indole can be in situ functionalized at the 3-position with alkyl halides or functionalized on the nitrogen with silyl chlorides. This method enables the synthesis of indoles with functional groups at each position of the indole backbone (C4–C7), providing handles for further functionalization.</div></div>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"6 2","pages":"Pages 171-178"},"PeriodicalIF":0.0,"publicationDate":"2025-05-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139988319","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Thioamide construction via sulfur interrupted Brook rearrangement","authors":"Shunmin Zhang , Yanyan Liao , Xuefeng Jiang","doi":"10.1016/j.gresc.2024.02.006","DOIUrl":"10.1016/j.gresc.2024.02.006","url":null,"abstract":"<div><div>Thioamide was straightforwardly constructed <em>via</em> a chemoselective one-pot synthesis, employing acylsilanes in conjunction with diverse amines and elemental sulfur. The driving force of thioamidation stemmed from silane migration, a synergy process of lone pair electron attack from amine and more stable Si–O bond formation, followed by the nucleophilic activation of elemental sulfur <em>via</em> carbanion intermediate. The leaving trend of trimethylsilanolate and nucleophilicity of linear polysulfur facilitated the cleavage of the S–S bond affording thioamide. A variety of sensitive functional groups, including unprotected hydroxyl, carboxyl and difluoride substitution moieties, are well tolerated under the reaction conditions. Site-selective introduction of thioamide was further demonstrated for the biologically active molecule linkage, displaying the advantages compared with the conventional Lawesson's reagent.</div></div>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"6 2","pages":"Pages 192-197"},"PeriodicalIF":0.0,"publicationDate":"2025-05-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140467031","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}