Yuanyun Gu 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 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":"https://doi.org/10.1016/j.gresc.2024.02.004","url":null,"abstract":"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 SAr 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 -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.","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"46 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-02-24","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}
Hong Qin, Man Yang, Yuguang Li, Xiaobing Yang, Yujing Hu, Chengkou Liu, Wei He, Zheng Fang, Kai Guo
{"title":"Synthesis of bridged bicyclic thiazine-2-thione and thiazole-2-thiones through DBU-promoted regioselective annulation of quinone monoacetals under mild conditions","authors":"Hong Qin, Man Yang, Yuguang Li, Xiaobing Yang, Yujing Hu, Chengkou Liu, Wei He, Zheng Fang, Kai Guo","doi":"10.1016/j.gresc.2023.12.004","DOIUrl":"https://doi.org/10.1016/j.gresc.2023.12.004","url":null,"abstract":"","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"29 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-02-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139946967","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":"https://doi.org/10.1016/j.gresc.2024.01.006","url":null,"abstract":"<p>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•, OH•, 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.</p>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"10 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-02-05","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}
Jun Chen, Rong Zhang, Caiyan Ma, Peng Zhang, Yonghong Zhang, Bin Wang, Fei Xue, Weiwei Jin, Yu Xia, Chenjiang Liu
{"title":"Sustainable electrochemical dearomatization for the synthesis of diverse 2, 3-functionalized indolines","authors":"Jun Chen, Rong Zhang, Caiyan Ma, Peng Zhang, Yonghong Zhang, Bin Wang, Fei Xue, Weiwei Jin, Yu Xia, Chenjiang Liu","doi":"10.1016/j.gresc.2022.10.009","DOIUrl":"https://doi.org/10.1016/j.gresc.2022.10.009","url":null,"abstract":"<div><p>Herein, we achieved a green and efficient dearomatization for the synthesis of 2,3-functionalized polycyclic indolines in an electrochemical way. This avoiding of external oxidants and metals approach allowed various nucleophilic sources (Nu = anilines, TMSN<sub>3</sub> and ROH) to perform the products, representing an environmentally benign means. Additionally, the continuous flow electrosynthesis and synthetic transformations also reveal the strong practicality of electrochemistry in organic synthesis.</p></div>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"5 1","pages":"Pages 25-30"},"PeriodicalIF":0.0,"publicationDate":"2024-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S2666554922001089/pdfft?md5=7b0adff8c270bf103561d51f07febc08&pid=1-s2.0-S2666554922001089-main.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139942549","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Photocatalytic generation of 1,4-disubstituted 1,2,3-triazoles under metal, oxidant and azide-free conditions","authors":"Changhong Liu, Dilshat Abdukerem, Wenli Zhu, Kun Xia, Zechuan Mao, Ablimit Abdukader","doi":"10.1016/j.gresc.2023.05.001","DOIUrl":"10.1016/j.gresc.2023.05.001","url":null,"abstract":"<div><p>Available online A mild and efficient photocatalytic-induced radical method has been developed for [4 + 1] cycloaddition reaction of 1,4-disubstituted 1,2,3-triazoles with <em>N</em>-tosylhydrazides and primary amines. The reaction is catalyzed by 20 mol% of I<sub>2</sub> under metal, azide and oxidant-free conditions. The method is based upon the photocatalytic generation of allyl-type radicals, followed by the iodine-catalyzed production of azoalkenes, which react rapidly with various anilines.</p></div>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"5 1","pages":"Pages 62-67"},"PeriodicalIF":0.0,"publicationDate":"2024-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S2666554923000509/pdfft?md5=7886140dff15b69729a90730a4226a33&pid=1-s2.0-S2666554923000509-main.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"77485290","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Letian Zhang , Kai Zheng , Pengfei Zhang , Min Jiang , Jiabin Shen , Chao Chen , Chao Shen
{"title":"Visible-light-enabled multicomponent synthesis of trifluoromethylated 3-indolequinoxalin-2(1H)-ones without external photocatalysis","authors":"Letian Zhang , Kai Zheng , Pengfei Zhang , Min Jiang , Jiabin Shen , Chao Chen , Chao Shen","doi":"10.1016/j.gresc.2022.08.002","DOIUrl":"10.1016/j.gresc.2022.08.002","url":null,"abstract":"<div><p>A novel and sustainable visible-light-enabled multicomponent reaction involving quinoxalin-2(1<em>H</em>)-ones, indoles, and CF<sub>3</sub>SO<sub>2</sub>Na that does not require an external photocatalyst is described. This photoinduced reaction employs air as the sole oxidant, thereby providing a green and highly step-efficient approach to a series of biologically important trifluoromethylated 3-indolequinoxalin-2(1<em>H</em>)-ones.</p></div>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"5 1","pages":"Pages 51-56"},"PeriodicalIF":0.0,"publicationDate":"2024-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S266655492200093X/pdfft?md5=0c74fc57f653a6b833398fbd339dc74c&pid=1-s2.0-S266655492200093X-main.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"88047896","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Agus Rimus Liandi , Antonius Herry Cahyana , Diva Naufal Alfariza , Rahma Nuraini , Renita Wulan Sari , Tio Putra Wendari
{"title":"Spirooxindoles: Recent report of green synthesis approach","authors":"Agus Rimus Liandi , Antonius Herry Cahyana , Diva Naufal Alfariza , Rahma Nuraini , Renita Wulan Sari , Tio Putra Wendari","doi":"10.1016/j.gresc.2023.08.001","DOIUrl":"10.1016/j.gresc.2023.08.001","url":null,"abstract":"<div><p>Spirooxindole is a compound with a unique framework and broad bioactivities in medicine. In this study, we have reviewed various approaches or methods in synthesizing spirooxindole derivatives focused on green synthesis. Synthesis of spirooxindoles is mainly carried out through multicomponent reactions combined with various green approaches such as the use of heterogeneous catalysts (nano-sized, magnetic, metal-complex, and metal-organic framework catalysts), deep eutectic solvent, solvent-free reactions, catalyst-free reactions, as well as the use of ultrasonic and microwaves irradiation. The green method is carried out in addition to obtaining high yields, it also offers reductions in the use of hazardous chemicals, energy use, purification processes, and waste generation. As a result, green synthesis methods in the synthesis of spirooxindole derivatives are more environmentally friendly.</p></div>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"5 1","pages":"Pages 1-13"},"PeriodicalIF":0.0,"publicationDate":"2024-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S2666554923000728/pdfft?md5=d515a34c8bc38e4ea04295a5c656f0a4&pid=1-s2.0-S2666554923000728-main.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"74396476","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Longzhou Qin , Xinpeng Zhang , Hao Sun , Xiu Duan , Jie Liu , Mengyu Wu , Xin Yuan , Jiangkai Qiu , Kai Guo
{"title":"Visible-light-induced decarboxylative alkynylation of carboxylic acids in batch and continuous flow","authors":"Longzhou Qin , Xinpeng Zhang , Hao Sun , Xiu Duan , Jie Liu , Mengyu Wu , Xin Yuan , Jiangkai Qiu , Kai Guo","doi":"10.1016/j.gresc.2022.10.002","DOIUrl":"10.1016/j.gresc.2022.10.002","url":null,"abstract":"<div><p>A green efficient photoredox-catalyzed decarboxylative alkynylation of carboxylic acids with alkynyl bromides has been developed. This broadly applicable protocol is presented wherein <em>α</em>-amino, aliphatic and <em>α</em>-oxy acids are converted into useful alkynylation products. The commercially-available organic photocatalyst 4CzIPN is used as the photocatalyst, organic base DBU is utilized as the base, and DMSO serves as solvent. This strategy features mild conditions, is metal-free, and is environmentally friendly. The batch and continuous-flow protocols described were applied to obtain a broader substrate scope of functionalization (more than 50 examples). Furthermore, we demonstrate that the use of microflow technology enhanced and intensified the reaction process, achieving significantly reduced reaction times (<em>i.e.</em>, 10 min of residence time).</p></div>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"5 1","pages":"Pages 20-24"},"PeriodicalIF":0.0,"publicationDate":"2024-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S2666554922001016/pdfft?md5=22dd76fdb3ccf1ecbefd227183083864&pid=1-s2.0-S2666554922001016-main.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"76483124","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}