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Divergent synthesis of new naphtho-fused 2-aminoindolines and naphthoxindoles based on straightforward construction of phenanthrene 基于直接构造菲的新型萘融合2-氨基吲哚和萘醌的发散合成
Green Synthesis and Catalysis Pub Date : 2025-02-01 DOI: 10.1016/j.gresc.2023.11.001
Bin Qiu , Ya-Fei Shi , Xiao-De An , Shu-Kui Guo , Yao-Bin Shen , Jian Xiao
{"title":"Divergent synthesis of new naphtho-fused 2-aminoindolines and naphthoxindoles based on straightforward construction of phenanthrene","authors":"Bin Qiu ,&nbsp;Ya-Fei Shi ,&nbsp;Xiao-De An ,&nbsp;Shu-Kui Guo ,&nbsp;Yao-Bin Shen ,&nbsp;Jian Xiao","doi":"10.1016/j.gresc.2023.11.001","DOIUrl":"10.1016/j.gresc.2023.11.001","url":null,"abstract":"<div><div>An environmentally friendly, highly atom-economical and operationally simple approach toward the synthesis of naphtho-fused 2-aminoindolines and naphthoxindoles starting from biaryl aldehydes and secondary amines has been developed. This notable methodology integrates consecutive intramolecular Mannich-type cyclization triggered by the dearomatization of indole with subsequent aromatization <em>via β</em>-elimination and then amination or oxidation at the C2-position of the indole nucleus. The secondary amine-controlled divergent protocol together with an easy product isolation process provides a practical route for the first time to access naphtho-fused 2-substituted indoline.</div></div>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"6 1","pages":"Pages 110-113"},"PeriodicalIF":0.0,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135615603","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
Photo-mediated para-selective C(sp2)−H difluoroalkylations 光介导的准选择性C(sp2)−H二氟烷基化反应
Green Synthesis and Catalysis Pub Date : 2025-02-01 DOI: 10.1016/j.gresc.2023.11.005
Yi Luo, Lin Dong
{"title":"Photo-mediated para-selective C(sp2)−H difluoroalkylations","authors":"Yi Luo,&nbsp;Lin Dong","doi":"10.1016/j.gresc.2023.11.005","DOIUrl":"10.1016/j.gresc.2023.11.005","url":null,"abstract":"<div><div>Photo-mediated ruthenium-catalyzed <em>para</em>-C−H difluoroalkylation has been disclosed under extremely mild conditions. This photochemical ruthenium catalyst system is characterized by good functional group compatibility without additional photosensitizers at room temperature.</div></div>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"6 1","pages":"Pages 91-95"},"PeriodicalIF":0.0,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138512297","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
Highly efficient palladacycle-catalyzed carboxylation of benzyl alcohols
Green Synthesis and Catalysis Pub Date : 2025-02-01 DOI: 10.1016/j.gresc.2024.08.005
Shaoke Zhang , Yan Zong , Yu Qian , Jishu Zhang , Gen-Qiang Chen , Xumu Zhang
{"title":"Highly efficient palladacycle-catalyzed carboxylation of benzyl alcohols","authors":"Shaoke Zhang ,&nbsp;Yan Zong ,&nbsp;Yu Qian ,&nbsp;Jishu Zhang ,&nbsp;Gen-Qiang Chen ,&nbsp;Xumu Zhang","doi":"10.1016/j.gresc.2024.08.005","DOIUrl":"10.1016/j.gresc.2024.08.005","url":null,"abstract":"<div><div>A general and practical carboxylation of benzyl alcohols using the air- and moisture-stable Herrmann-Beller palladacycle was developed. With this novel methodology, numerous carboxylated products were constructed and various functional groups were tolerated. More specifically, some prevailing <em>anti</em>-inflammatory drugs, Ibuprofen, Naproxen, Fenoprofen and Flurbiprofen were all successfully synthesized with this novel procedure. Gram scale experiments revealed the industrial potentiality of this procedure. Several interesting control experiments were performed, and the general reaction pathway was proposed.</div></div>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"6 1","pages":"Pages 119-122"},"PeriodicalIF":0.0,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143507930","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
Asymmetric synthesis of chiral heterobenzylic amines via visible-light-induced enantioselective C(sp3)-H alkylation 可见光诱导对映选择性C(sp3)-H烷基化不对称合成手性杂酶胺
Green Synthesis and Catalysis Pub Date : 2025-02-01 DOI: 10.1016/j.gresc.2023.11.004
Yumei Huo , Beibei Chen , Xiaoyu Ren , Chao Wang , Rupeng Qi , Zhaoqing Xu
{"title":"Asymmetric synthesis of chiral heterobenzylic amines via visible-light-induced enantioselective C(sp3)-H alkylation","authors":"Yumei Huo ,&nbsp;Beibei Chen ,&nbsp;Xiaoyu Ren ,&nbsp;Chao Wang ,&nbsp;Rupeng Qi ,&nbsp;Zhaoqing Xu","doi":"10.1016/j.gresc.2023.11.004","DOIUrl":"10.1016/j.gresc.2023.11.004","url":null,"abstract":"<div><div>The chiral heterobenzylic amines, such as <em>α</em>-alkyl substituted chiral oxadiazole methylamine skeletons are widely present in pesticides and pharmaceuticals, due to their unique biological activities. The enantioselective C(sp<sup>3</sup>)-H alkylation of heterobenzylic amines is an important strategy for the synthesis of <em>α</em>-alkylate chiral heterobenzylic amines. Herein, we disclose the first example of photoinduced and Cu-catalyzed enantioselective decarboxylative C(sp<sup>3</sup>)-H alkylation of oxadiazole methylamines.</div></div>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"6 1","pages":"Pages 114-118"},"PeriodicalIF":0.0,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138512302","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
Palladium-catalyzed intramolecular C–H arylation of ferrocenyl-sulfides, sulfoxide and its application in metal ion recognition 钯催化二茂铁基硫化物、亚砜的分子内C-H基化及其在金属离子识别中的应用
Green Synthesis and Catalysis Pub Date : 2025-02-01 DOI: 10.1016/j.gresc.2023.11.011
Feifei Cao , Congyu Gao , Jingxin Zi , Jianfeng Hu , Yong Yang , Wen-Xiong Zhang , Hao Zhang
{"title":"Palladium-catalyzed intramolecular C–H arylation of ferrocenyl-sulfides, sulfoxide and its application in metal ion recognition","authors":"Feifei Cao ,&nbsp;Congyu Gao ,&nbsp;Jingxin Zi ,&nbsp;Jianfeng Hu ,&nbsp;Yong Yang ,&nbsp;Wen-Xiong Zhang ,&nbsp;Hao Zhang","doi":"10.1016/j.gresc.2023.11.011","DOIUrl":"10.1016/j.gresc.2023.11.011","url":null,"abstract":"<div><div>An intramolecular C–H arylation of ferrocenyl <em>ortho</em>-bromophenyl sulfide and sulfoxide has been developed with a palladium/non-chiral monophosphine ligand. Under mild reaction conditions, a wide range of ferrocene cyclosulfide and ferrocene cyclosulfoxide were obtained in up to 90 ​% yield. Moreover, planar chiral ferrocene cyclosulfide with enantioselectivities (up to 45 ​% <em>ee</em>) was synthesized utilizing chiral phosphine ligands. Furthermore, the compound <strong>4a</strong> and <strong>6a</strong> can be used as novel chemosensors to detect Cu<sup>2+</sup> ion.</div></div>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"6 1","pages":"Pages 67-74"},"PeriodicalIF":0.0,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138512317","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
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 : 2025-02-01 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 ,&nbsp;Ming-Hua Xu","doi":"10.1016/j.gresc.2023.12.002","DOIUrl":"10.1016/j.gresc.2023.12.002","url":null,"abstract":"<div><div>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.</div></div>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"6 1","pages":"Pages 86-90"},"PeriodicalIF":0.0,"publicationDate":"2025-02-01","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":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Chemo- and diastereoselective four-component reactions with Rh carbynoids
Green Synthesis and Catalysis Pub Date : 2025-02-01 DOI: 10.1016/j.gresc.2024.10.006
Mengchu Zhang , Xiaoyan Yang , Xiang Fu , Xiaoyu Zhou , Yu Qian , Wenhao Hu
{"title":"Chemo- and diastereoselective four-component reactions with Rh carbynoids","authors":"Mengchu Zhang ,&nbsp;Xiaoyan Yang ,&nbsp;Xiang Fu ,&nbsp;Xiaoyu Zhou ,&nbsp;Yu Qian ,&nbsp;Wenhao Hu","doi":"10.1016/j.gresc.2024.10.006","DOIUrl":"10.1016/j.gresc.2024.10.006","url":null,"abstract":"<div><div>Multi-component reactions (MCRs) provide an efficient method for constructing multiple chemical bonds by combining three or more starting materials in a single operational step, enabling rapid and cost-effective synthesis of structurally diverse compounds. Although carbynoids (R-C:+) have shown potential for the development of selective MCRs due to their unique carbene and carbocation characteristics, their application in four-component reactions (4CRs) has been constrained by challenges in chemoselectivity. Herein, we provide a general solution to the challenges of chemoselective 4CR, using halo diazo reagents as carbynoid precursors, followed by reacting with pyrazoles, alcohols and imines sequentially. This approach allows the simultaneous construction of three different <em>C</em> (<em>sp</em><sup><em>3</em></sup>)-<em>N</em>, <em>C</em> (<em>sp</em><sup><em>3</em></sup>)-<em>O</em>, and <em>C</em> (<em>sp</em><sup><em>3</em></sup>)-<em>C</em> (<em>sp</em><sup><em>3</em></sup>) bonds on the same carbon. The success of this protocol mainly depends on precise control of chemical kinetics. Detailed experimental studies elucidate that the generation rate of <em>aza</em>-Rh(II)-carbene is faster than <em>oxy</em>-Rh(II)-carbene.</div></div>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"6 1","pages":"Pages 101-105"},"PeriodicalIF":0.0,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143507929","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
Sustainable synthetic routes to deuterium-labelled organic compounds using immobilized and recyclable (bio)catalysts
Green Synthesis and Catalysis Pub Date : 2025-02-01 DOI: 10.1016/j.gresc.2024.09.008
Luka Jedlovčnik , Jakob Höfferle , Aljaž Gaber , Fjoralb Pashaj , Jerneja Kladnik , Janez Košmrlj , Volker Derdau , Ross D. Jansen-van Vuuren
{"title":"Sustainable synthetic routes to deuterium-labelled organic compounds using immobilized and recyclable (bio)catalysts","authors":"Luka Jedlovčnik ,&nbsp;Jakob Höfferle ,&nbsp;Aljaž Gaber ,&nbsp;Fjoralb Pashaj ,&nbsp;Jerneja Kladnik ,&nbsp;Janez Košmrlj ,&nbsp;Volker Derdau ,&nbsp;Ross D. Jansen-van Vuuren","doi":"10.1016/j.gresc.2024.09.008","DOIUrl":"10.1016/j.gresc.2024.09.008","url":null,"abstract":"<div><div>Deuterium(D)-labelled organic compounds are used in many applications <em>e.g</em>., as therapeutic agents, internal standards in drug discovery and development, and new functional materials including dyes, catalysts, and light emitters. Conventionally, the synthesis of D-labelled compounds relies on (bio)catalysts due to their regio- and stereoselectivity, mild reaction conditions, and treatment of a broad scope of substrates. However, most (bio)catalysts are expensive to prepare/isolate, and some contain precious metals (PMs), <em>e.g.</em>, Ir, Pd, whose markets are unpredictable, and which need to be separated from the products at great expense, post-reaction. With the general shift away from traditional ‘make-use-dispose’ approaches to ones that are less wasteful, the use of recyclable catalysts in both batch and continuous flow systems are increasingly employed. In this work, we comprehensively and critically review the catalysts and immobilization and recycling strategies implemented for the preparation of D-labelled organic compounds. Our aim is to highlight the most effective advances and expose the gaps in the literature to inform future research.</div></div>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"6 1","pages":"Pages 1-35"},"PeriodicalIF":0.0,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143508072","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
Light-induced perfluoroalkylative carbonylation of unactivated alkenes with a recyclable photocatalyst 利用可回收光催化剂对未活化烯烃进行光诱导全氟烷基羰基化反应
Green Synthesis and Catalysis Pub Date : 2025-02-01 DOI: 10.1016/j.gresc.2024.05.002
Heng Yang , Shuyu Yang , Xiao-Feng Wu , Feng Chen
{"title":"Light-induced perfluoroalkylative carbonylation of unactivated alkenes with a recyclable photocatalyst","authors":"Heng Yang ,&nbsp;Shuyu Yang ,&nbsp;Xiao-Feng Wu ,&nbsp;Feng Chen","doi":"10.1016/j.gresc.2024.05.002","DOIUrl":"10.1016/j.gresc.2024.05.002","url":null,"abstract":"<div><div>The development of heterogeneous catalysis difunctionalization of olefins is of great significance because it can save costs in the industry. Here, we report the perfluoroalkyl carbonylation reaction of inactive olefins catalyzed by titanium dioxide under light, obtaining <em>β</em>-perfluoroalkylamide compounds. The catalyst has high activity and wide functional group tolerance and can maintain high activity after multiple cycles. This catalyst reduces the use of precious metals, avoids ligands, and can easily be separated from the reaction mixtures.</div></div>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"6 1","pages":"Pages 81-85"},"PeriodicalIF":0.0,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141043378","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
Sulfone as traceless activating group: Divergent synthesis of α-fluoroamides with C–F quaternary stereocenters
Green Synthesis and Catalysis Pub Date : 2025-02-01 DOI: 10.1016/j.gresc.2024.09.006
Jieqing Wu , Liying Fu , Renyi Diao , Longjun Nie , Chi Zhang , Yufeng Li , Chao Feng
{"title":"Sulfone as traceless activating group: Divergent synthesis of α-fluoroamides with C–F quaternary stereocenters","authors":"Jieqing Wu ,&nbsp;Liying Fu ,&nbsp;Renyi Diao ,&nbsp;Longjun Nie ,&nbsp;Chi Zhang ,&nbsp;Yufeng Li ,&nbsp;Chao Feng","doi":"10.1016/j.gresc.2024.09.006","DOIUrl":"10.1016/j.gresc.2024.09.006","url":null,"abstract":"<div><div>A novel approach to <em>α</em>-fluoroamides bearing a C–F quaternary stereocenter is reported herein. With sulfone installed as the activating group, an alkyl group as well as a fluorine atom was introduced successively under mild conditions. Subsequently, heterolytic fission of the C–S bond occurred smoothly under photoredox conditions to afford a tertiary radical, which then engaged in varied intramolecular cyclizations depending on substrate structure and condition applied, rendering sulfone an overall traceless activating group.</div></div>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"6 1","pages":"Pages 96-100"},"PeriodicalIF":0.0,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143507927","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
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