Green Synthesis and Catalysis最新文献

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Photomediated core modification of diaryl dihydrophenzines through three-component alkylarylation of alkenes toward organocatalyzed ATRP 通过烯烃的三组分烷基芳基化实现二芳基二氢苯胺的光催化核心改性,从而实现有机催化 ATRP
Green Synthesis and Catalysis Pub Date : 2024-02-01 DOI: 10.1016/j.gresc.2022.12.001
Yajun Zhang , Hao Wang , Dandan Jiang , Naixian Sun , Wei He , Lili Zhao , Ning Qin , Ning Zhu , Zheng Fang , Kai Guo
{"title":"Photomediated core modification of diaryl dihydrophenzines through three-component alkylarylation of alkenes toward organocatalyzed ATRP","authors":"Yajun Zhang ,&nbsp;Hao Wang ,&nbsp;Dandan Jiang ,&nbsp;Naixian Sun ,&nbsp;Wei He ,&nbsp;Lili Zhao ,&nbsp;Ning Qin ,&nbsp;Ning Zhu ,&nbsp;Zheng Fang ,&nbsp;Kai Guo","doi":"10.1016/j.gresc.2022.12.001","DOIUrl":"10.1016/j.gresc.2022.12.001","url":null,"abstract":"<div><p>The design and synthesis of a novel organic photocatalyst (OPC) have attracted broad interest from both the organic chemistry and polymer community. Herein, we presented a visible-light-induced alkylarylation of alkenes strategy for core modification of 5,10-diaryl-5,10-dihydrophenazines (DADHPs) under metal- and additive-free conditions, with the aim to develop powerful photocatalyst for organocatalyzed atom transfer radical polymerization (O-ATRP). Good tolerance for a wide variety of functional groups and affording the corresponding tetrasubstituted products in moderate to good yields were achieved in the batch and flow reactor. The experimental and computational mechanistic study confirmed that DADHPs’ radical cations and <em>π</em>-<em>π</em> stacking interactions played important roles in the alkylarylation of alkenes. A series of the tetrasubstituted DADHPs were directly synthesized from the corresponding noncore-modified phenazines, which were demonstrated to be effective organic photoredox catalysts for O-ATRP. Light responsive nature, controlled polymerization manner, and well-defined poly (methyl methacrylate) were achieved <em>via</em> tetrasubstituted DADHPs mediated O-ATRP.</p></div>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"5 1","pages":"Pages 35-41"},"PeriodicalIF":0.0,"publicationDate":"2024-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S2666554922001302/pdfft?md5=bd81e1627ca2a248b71ff00bfe3e254e&pid=1-s2.0-S2666554922001302-main.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"89769408","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}
引用次数: 0
Photoinduced radical cascade brominative addition/spirocyclization of N-arylpropiolamides and CBr4 with O2 as oxidant 以 O2 为氧化剂,光诱导 N-芳基丙炔酰胺和 CBr4 的自由基级联溴化加成/螺环化反应
Green Synthesis and Catalysis Pub Date : 2024-01-15 DOI: 10.1016/j.gresc.2024.01.004
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":"https://doi.org/10.1016/j.gresc.2024.01.004","url":null,"abstract":"<p>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.</p>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"11 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-01-15","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}
引用次数: 0
Electrochemical N-olefination for the regio- and stereo-selective synthesis of vinyl azoles 电化学 N-olefination 技术用于乙烯基唑的区域和立体选择性合成
Green Synthesis and Catalysis Pub Date : 2024-01-12 DOI: 10.1016/j.gresc.2024.01.005
Kejun Lin, Jianyong Lan, Lin Hao, Tingshun Zhu
{"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":"https://doi.org/10.1016/j.gresc.2024.01.005","url":null,"abstract":"<p>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 &gt; 20:1 <em>Z/E</em> ratio.</p>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"211 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-01-12","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}
引用次数: 0
Directed evolution of stereoselective enzymes meets click reactions: asymmetric synthesis of chiral triazoles using a Cu(I)-compatible halohydrin dehalogenase 立体选择性酶的定向进化与点击反应:使用 Cu(I)兼容卤代卤化酶不对称合成手性三唑
Green Synthesis and Catalysis Pub Date : 2024-01-12 DOI: 10.1016/j.gresc.2024.01.001
Shaixiao Tian, Xinying Ge, Qipeng Yan, Min Li, Qun Huang, Xinhua Zhang, Ming Ma, Bo Chen, Jian-bo Wang
{"title":"Directed evolution of stereoselective enzymes meets click reactions: asymmetric synthesis of chiral triazoles using a Cu(I)-compatible halohydrin dehalogenase","authors":"Shaixiao Tian, Xinying Ge, Qipeng Yan, Min Li, Qun Huang, Xinhua Zhang, Ming Ma, Bo Chen, Jian-bo Wang","doi":"10.1016/j.gresc.2024.01.001","DOIUrl":"https://doi.org/10.1016/j.gresc.2024.01.001","url":null,"abstract":"<p>We report for the first time the combination of directed evolution focused on enhancing and reversing the stereoselectivity of an enzyme with Cu(I)-mediated click chemistry (CuAAC), providing an asymmetric click approach for versatile chiral triazoles products. In this study, the halohydrin dehalogenase HheG was used as the enzyme which was evolved to induce a stereoselective ring-opening reaction of cyclic epoxides in the presence of NaN<sub>3</sub> with the formation of chiral azido products. Two mutants of opposite stereopreference were generated, which convert cyclohexene oxide as well as cycloheptene oxide to (1<em>S</em>, 2<em>S</em>)-2-azidocyclohexanol, (1<em>R</em>, 2<em>R</em>)-2-azidocyclohexanol, (1<em>S</em>, 2<em>S</em>)-2-azidocycloheptanol and (1<em>R</em>, 2<em>R</em>)-2-azidocycloheptanol with essentially high stereoselectivity. The chiral products were then subjected to CuAAC in reactions with structurally different alkynes. Since HheG was found to be compatible with Cu(I), the process was also performed successfully in a unique 2-step one-pot process leading to various chiral triazoles. In order to understand the enhancement and reversal of the evolved enantioselectivity, QM and MD computations were performed. This approach harnesses the modifiability and high stereoselectivity of the evolved biocatalysts in combination with click chemistry. It holds great potential for diverse fields, particularly in the area of pharmaceuticals.</p>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"34 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-01-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139463230","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}
引用次数: 0
Controlled generation of ortho-quinone methides and (4+3) cyclization with 2-indolylalcohols by dual photoredox/Brønsted acid relay catalysis 通过光氧化/勃氏酸双重中继催化控制生成邻醌甲酰胺并与 2-吲哚基乙醇发生 (4+3) 环化反应
Green Synthesis and Catalysis Pub Date : 2024-01-09 DOI: 10.1016/j.gresc.2024.01.002
Dong Liang, Panpan Gao, Zhihan Zhang, Wenjing Xiao, Jiarong Chen
{"title":"Controlled generation of ortho-quinone methides and (4+3) cyclization with 2-indolylalcohols by dual photoredox/Brønsted acid relay catalysis","authors":"Dong Liang, Panpan Gao, Zhihan Zhang, Wenjing Xiao, Jiarong Chen","doi":"10.1016/j.gresc.2024.01.002","DOIUrl":"https://doi.org/10.1016/j.gresc.2024.01.002","url":null,"abstract":"<p>Given the significance of oxacyclic frameworks in molecular scaffolds and drug discovery, it is intriguing to precisely construct and manipulate such ring systems in chemical research. In this area, the intermolecular, multicomponent cyclization for the synthesis of diversely substituted seven-membered ring oxacycles under simple conditions is still a challenge. Here, we report a dual photoredox/Brønsted acid relay catalytic strategy for in situ generation of <em>ortho</em>-quinone methides and subsequent (4+3) cyclization with 2-indolylalcohols. In this one-pot multicomponent reaction, two C-C and one C-O bonds are formed, providing de novo access to various biologically important indole-fused, oxygen-containing seven-membered heterocycles. By virtue of a chiral phosphoric acid, an asymmetric version can also be achieved with good to excellent levels of enantioselectivity (up to 96:4 er).</p>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"111 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-01-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139410353","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}
引用次数: 0
Visible-light-induced reusable decatungstate-photocatalyzed radical cascade alkylation/cyclization of isocyanides with simple alkanes, ethers and ketones 可见光诱导的可重复使用的十钨酸盐光催化自由基级联烷基化/异氰酸酯与简单烷烃、醚和酮的环化反应
Green Synthesis and Catalysis Pub Date : 2024-01-06 DOI: 10.1016/j.gresc.2024.01.003
Ke-Li Wang, Hong-Tao Ji, Qiong-Hui Peng, Jun Jiang, Li-Juan Ou, Wei-Min He
{"title":"Visible-light-induced reusable decatungstate-photocatalyzed radical cascade alkylation/cyclization of isocyanides with simple alkanes, ethers and ketones","authors":"Ke-Li Wang, Hong-Tao Ji, Qiong-Hui Peng, Jun Jiang, Li-Juan Ou, Wei-Min He","doi":"10.1016/j.gresc.2024.01.003","DOIUrl":"https://doi.org/10.1016/j.gresc.2024.01.003","url":null,"abstract":"<p>With reusable sodium decatungstate (NaDT) as the photocatalyst, hydrocarbons (alkanes, ethers and ketones) as the alkylating agents, a wide range of alkylated fused <em>N</em>-heterocycles were obtained in high yield.</p>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"116 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-01-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139374048","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}
引用次数: 0
Water-controlled skeletal editing or peripheral modification of ortho-chalcone-substituted organophosphines 水控制的骨架编辑或外围修饰邻位丙酮取代的有机膦
Green Synthesis and Catalysis Pub Date : 2024-01-05 DOI: 10.1016/j.gresc.2023.12.003
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":"https://doi.org/10.1016/j.gresc.2023.12.003","url":null,"abstract":"<p>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.</p>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"50 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-01-05","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}
引用次数: 0
Facile synthesis of asymmetric tetrablock copolymer by dual thermal and photochemical initiator 利用双重热引发剂和光化学引发剂轻松合成不对称四嵌段共聚物
Green Synthesis and Catalysis Pub Date : 2023-12-18 DOI: 10.1016/j.gresc.2023.11.009
Chenhuai Deng, Yuanhao Lin, Yunye Huang, Linxi Hou, Longqiang Xiao
{"title":"Facile synthesis of asymmetric tetrablock copolymer by dual thermal and photochemical initiator","authors":"Chenhuai Deng, Yuanhao Lin, Yunye Huang, Linxi Hou, Longqiang Xiao","doi":"10.1016/j.gresc.2023.11.009","DOIUrl":"https://doi.org/10.1016/j.gresc.2023.11.009","url":null,"abstract":"<p>Vesicles obtained by the self-assembly of asymmetric tetrablock copolymers are a class of materials with fascinating properties. However, simple strategies to synthesize asymmetric tetrablock copolymers are limited. Herein, we have designed and synthesized an initiator which generates radicals by either heating or photoirradiation. Taking the advantages of organocatalyzed reversible complexation mediated radical polymerization which has lower energy requirements, milder reaction conditions, and reduced generation of hazardous byproducts, a three steps synthetic route following \"photo-photo-thermal\" initiation condition for the preparation of asymmetric CABC tetrablock copolymers with controllable molecular weight, precise block composition and low polydispersity was developed.</p>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"6 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2023-12-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138744802","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}
引用次数: 0
Synthesis of dydrogesterone by aromatization-dearomatization strategy 通过芳香化-脱芳香化策略合成地屈孕酮
Green Synthesis and Catalysis Pub Date : 2023-12-15 DOI: 10.1016/j.gresc.2023.12.001
Heng Bai, Wei Gu, Di Zhao, Guangqing Xu, Wenjun Tang
{"title":"Synthesis of dydrogesterone by aromatization-dearomatization strategy","authors":"Heng Bai, Wei Gu, Di Zhao, Guangqing Xu, Wenjun Tang","doi":"10.1016/j.gresc.2023.12.001","DOIUrl":"https://doi.org/10.1016/j.gresc.2023.12.001","url":null,"abstract":"<p>Dydrogesterone as an agonist of the progesterone receptor is an important and selective synthetic progesterone used for the treatment of a variety of conditions associated with progesterone deficiency including menstrual cycle regulation, infertility, and prevention of miscarriage. Its manufacturing process employing photochemical reactions remains a significant challenge. Herein we report the first total synthesis of dydrogesterone <em>via</em> a key 10α-substitution-selective dearomative cyclizationfree of photochemical protocols starting from Hajos-Parrish ketone. A gram-scale synthesis is also accomplished from readily available 9-hydroxy-4-androstene-3,17-dione through a novel aromatization-dearomatization strategy of ring A in steroid chemistry. Key synthetic features include a facile chemical aromatization of 9-hydroxy-4-androstene-3,17-dione, efficient ligand-controlled asymmetric dearomative cyclization to install the 10<em>α</em>-Me group, and an effective hydroxyl-directed hydrogenation of sterically congested tetrasubstituted olefin to establish the 8<em>β</em>-H,9<em>β</em>-H stereochemistry.</p>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"87 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2023-12-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138689940","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}
引用次数: 0
Brønsted acid promoted synthesis of polysubstituted pyrroles from enamines/imines and diazopyruvates: a metal-free cascade approach 在布氏酸的促进下,从烯胺/亚胺和重氮丙酮酸盐合成多代吡咯:一种无金属级联方法
Green Synthesis and Catalysis Pub Date : 2023-12-13 DOI: 10.1016/j.gresc.2023.12.002
Farrukh Sajjad, Ming-Hua Xu
{"title":"Brønsted acid promoted synthesis of polysubstituted pyrroles from enamines/imines and diazopyruvates: a metal-free cascade approach","authors":"Farrukh Sajjad, Ming-Hua Xu","doi":"10.1016/j.gresc.2023.12.002","DOIUrl":"https://doi.org/10.1016/j.gresc.2023.12.002","url":null,"abstract":"<p>A Brønsted acid-promoted, metal-free cascade reaction of easily available enamines/imines with diazopyruvates has been demonstrated. With triflic acid as the promoter, the reaction proceeds smoothly at room temperature through sequential diazo protonation, nucleophilic enamine N-addition/C-addition and dehydrative aromatisation in a highly regioselective manner. Interestingly, the regioselectivity of the reaction is governed by the unusual enamine N-nucleophilic addition. The method provides an operationally trivial approach to the synthesis of multisubstituted pyrroles including tri-, tetra-, and penta-substituted derivatives as well as N-H free pyrroles with diverse functionalities in good yields under extraordinarily simple and mild conditions. The utility of the method is illustrated by the rapid assembly of polysubstituted bispyrroles and an array of diversely structured pyrrole derivatives.</p>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"5 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2023-12-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138679683","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}
引用次数: 0
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