{"title":"Catalyst-free and atom-economical [4+3] cycloaddition of azadienes with cyclic azomethine imines for facile synthesis of 1,2,4-triazepines","authors":"Lesong Li , Tao Liu , Weiwu Ren , Yang Wang","doi":"10.1016/j.gresc.2022.10.010","DOIUrl":"10.1016/j.gresc.2022.10.010","url":null,"abstract":"<div><p>A catalyst-free and atom-economical [4 + 3] cycloaddition of azadienes with <em>C</em>,<em>N</em>-cyclic azomethine imines has been developed, providing an efficient and environmentally benign access to 1,2,4-triazepines with high diastereoselectivities and yields. This reaction can be performed in 2-methyltetrahydrofuran under mild conditions smoothly.</p></div>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"5 1","pages":"Pages 57-61"},"PeriodicalIF":0.0,"publicationDate":"2024-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S2666554922001090/pdfft?md5=35bfc7b8c13710d438eb5df294da0ef1&pid=1-s2.0-S2666554922001090-main.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"84930088","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}
Pu-Zhang Zi, Xing-Bang Liu, Quan-Hong Zhao, Min He, Yuan Huang
{"title":"1,6-Conjugate addition of para-quinone methides using gem-diborylcarbanions: Practical access to gem-diborylalkanes bearing vicinal tertiary/quaternary stereocenters","authors":"Pu-Zhang Zi, Xing-Bang Liu, Quan-Hong Zhao, Min He, Yuan Huang","doi":"10.1016/j.gresc.2022.12.003","DOIUrl":"10.1016/j.gresc.2022.12.003","url":null,"abstract":"<div><p>A novel, efficient and pragmatic method to prepare <em>gem</em>-diboron products with vicinal tertiary/quaternary stereocenters using LiTMP-mediated 1,6-conjugate addition of <em>gem</em>-diborylalkanes to <em>para-</em>quinone methides was described for the first time. The results showed that various <em>gem</em>-diboron products with vicinal tertiary and quaternary stereocenters could be formed within 15 min at ambient temperature. This simple protocol has also been applied for the efficient synthesis of the analogue of Bedaquiline.</p></div>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"5 1","pages":"Pages 68-72"},"PeriodicalIF":0.0,"publicationDate":"2024-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S2666554922001326/pdfft?md5=3314d38e0d2dab17275278bc0d437ec2&pid=1-s2.0-S2666554922001326-main.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"77603679","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}
Dahan Wang , Yuhan Yang , Fuhong Xiao , Jinbing Liu , Guojiang Mao , Guo-Jun Deng
{"title":"Synthesis of biheteroaryls via 2-methyl quinoline C(sp3)-H functionalization under metal-free conditions","authors":"Dahan Wang , Yuhan Yang , Fuhong Xiao , Jinbing Liu , Guojiang Mao , Guo-Jun Deng","doi":"10.1016/j.gresc.2022.10.006","DOIUrl":"10.1016/j.gresc.2022.10.006","url":null,"abstract":"<div><p>An acetic acid-promoted C(sp<sup>3</sup>)-H functionalization of 2-methyl quinoline, enaminoesters and elemental sulfur for the synthesis of 3,4,5-trisubstituted isothiazoles under metal-free conditions has been developed. This approach provides viable access to various 5-(quinolin-2-yl)isothiazoles in moderate to good yields with good functional group tolerance. Moreover, the success of the gram-scale reaction gives this reaction a great potential application.</p></div>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"5 1","pages":"Pages 73-76"},"PeriodicalIF":0.0,"publicationDate":"2024-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S2666554922001053/pdfft?md5=220913039ea20657a83f856f3a835258&pid=1-s2.0-S2666554922001053-main.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"76330609","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}
Yimiao He , Jingwen Yuan , Wen-Xin Lv , Peng Liu , Fan Teng , Qijin Mo , Zihua Wu , Chusheng Huang , Qianwen Liu , Honggen Wang
{"title":"Simple nucleophile/H2O promoted defluorinative ring-opening of gem-difluorocyclopropenes","authors":"Yimiao He , Jingwen Yuan , Wen-Xin Lv , Peng Liu , Fan Teng , Qijin Mo , Zihua Wu , Chusheng Huang , Qianwen Liu , Honggen Wang","doi":"10.1016/j.gresc.2023.01.003","DOIUrl":"10.1016/j.gresc.2023.01.003","url":null,"abstract":"<div><p>A novel defluorinative ring-opening of <em>gem</em>-difluorocyclopropenes is presented, providing a concise and efficient method for accessing 2-fluoropropenals and 2-fluorobuta-1,3-dienes in moderate to good yields with excellent regio- and stereoselectivities. The reaction is performed under mild conditions with no need of using an excess amount of nucleophilic reagents. Water plays a crucial role in this transformation.</p></div>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"5 1","pages":"Pages 14-19"},"PeriodicalIF":0.0,"publicationDate":"2024-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S2666554923000030/pdfft?md5=e3c9ee925032e222f7ef4f524070100c&pid=1-s2.0-S2666554923000030-main.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"90239739","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}
Xin Han, Luyao Ding, Xin-Qi Hao, Yujing Guo, Linlin Shi
{"title":"A water-soluble supermolecular cage for artificial light-harvesting nanoreactors","authors":"Xin Han, Luyao Ding, Xin-Qi Hao, Yujing Guo, Linlin Shi","doi":"10.1016/j.gresc.2024.01.007","DOIUrl":"https://doi.org/10.1016/j.gresc.2024.01.007","url":null,"abstract":"<p>Two discrete octahedral metallo-supramolecular cages were designed and constructed by using truxene-based pyridine <strong>L</strong> with enPd(NO<sub>3</sub>)<sub>2</sub> or enPt(NO<sub>3</sub>)<sub>2</sub>, followed by detailed NMR, MS, UV absorption, and fluorescence spectroscopy. Owing to the determined cavity size and excellent optical performance of cages, the resulting supramolecular cages were confirmed to be the light-harvesting system based on Föster resonance energy-transfer (FRET). The developed cages display good water solubilities and can act as nanoreactors and light-harvesting systems to catalyze the difluoromethylation of quinoxalin-2(1<em>H</em>)-ones with sodium difluoromethanesulfinate under the irradiation of sunlight. Compared with eosin Y alone, this system displayed enhanced catalytic activity in catalyzing the difluoromethylation, which realizes the simulation of the photosynthesis process.</p>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"1 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139665359","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":"Visible-light-promoted tandem decarboxylation coupling/cyclization of N-aryl glycines with quinoxalinones: Easy access to tetrahydroimidazo[1,5-a]quinoxalin-4(5H)-ones","authors":"Zhen Tang, Chao Pi, Yangjie Wu, Xiuling Cui","doi":"10.1016/j.gresc.2022.10.001","DOIUrl":"https://doi.org/10.1016/j.gresc.2022.10.001","url":null,"abstract":"<div><p>A visible-light-promoted formal [2 + 2 + 1] cyclization of <em>N</em>-aryl glycines with quinoxalin-2(1<em>H</em>)-ones to synthesize tetrahydroimidazo[1,5-<em>a</em>]quinoxalin-4(5<em>H</em>)-ones have been developed. The protocol features operational simplicity, mild reaction conditions with blue LED light employing Ru(bpy)<sub>3</sub>Cl<sub>2</sub><sup>.</sup>6H<sub>2</sub>O as a photoredox catalyst, a combination of O<sub>2</sub> from air and Cu(OAc)<sub>2</sub> as the oxidant and broad substrate applicability.</p></div>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"5 1","pages":"Pages 31-34"},"PeriodicalIF":0.0,"publicationDate":"2024-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S2666554922001004/pdfft?md5=8255ec7eec8de00b3538ee29cf98d646&pid=1-s2.0-S2666554922001004-main.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139942553","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}
Jia Zhang , Jian Yang , Xuemei Li , Bin Mu , Hailong Liu , Chungu Xia , Aiqin Wang , Zhiwei Huang
{"title":"Natural attapulgite supported nano-Ni catalysts for the efficient reductive amination of biomass-derived aldehydes and ketones","authors":"Jia Zhang , Jian Yang , Xuemei Li , Bin Mu , Hailong Liu , Chungu Xia , Aiqin Wang , Zhiwei Huang","doi":"10.1016/j.gresc.2023.02.003","DOIUrl":"10.1016/j.gresc.2023.02.003","url":null,"abstract":"<div><p>The efficient synthesis of useful primary amines <em>via</em> reductive amination of biomass-based aldehydes and ketones over earth-abundant base metal catalysts is an attractive biomass value-adding technology yet facing lots of challenges. Herein, natural attapulgite (ATP) was applied as support for the fabrication of active Ni catalysts with different Ni loadings (5–30 wt%) by the deposition-precipitation method. The Ni/ATP-550 catalyst with 10–15 wt% Ni loadings was found to present the highest catalytic performance for the synthesis of valuable 5-amino-1-pentanol (5-AP) <em>via</em> reductive amination of biofurfural-derived 2-hydroxytetrahydropyran among a variety of commonly used oxide supports loaded Ni catalysts, as well as ATP supported nickel catalysts with other loadings, achieving 5-AP yield up to 94%. The intrinsic activity of the Ni/ATP catalysts was found to depend strongly on the Ni<sup>0</sup> crystallite size and Ni<sup>0</sup> fraction of the catalysts, which generally increased with increasing Ni<sup>0</sup> crystallite size and fraction, owing probably to the hydrogenation of imine intermediate is a structure-sensitive reaction. The efficient 10Ni/ATP-550 catalyst also exhibited good activity and stability in the reductive amination of several other biomass-derived aldehydes and ketones to their corresponding primary amines with good to excellent yields (81%–99%). This work provided a clean and efficient natural ATP-supported non-noble metal nickel-based catalytic system for the reductive amination of aldehydes and ketones to synthesize high-value-added primary amines, which could be a promising candidate for the industrial production of amines.</p></div>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"5 1","pages":"Pages 42-50"},"PeriodicalIF":0.0,"publicationDate":"2024-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S2666554923000248/pdfft?md5=c2825c7eabef2243b4ead423d14f2aa4&pid=1-s2.0-S2666554923000248-main.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135962667","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}