Pub Date : 2025-02-01Epub Date: 2023-12-13DOI: 10.1016/j.gresc.2023.12.002
Farrukh Sajjad , Ming-Hua Xu
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.
{"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":"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}
Pub Date : 2025-02-01Epub Date: 2024-10-28DOI: 10.1016/j.gresc.2024.10.006
Mengchu Zhang , Xiaoyan Yang , Xiang Fu , Xiaoyu Zhou , Yu Qian , Wenhao Hu
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 C (sp3)-N, C (sp3)-O, and C (sp3)-C (sp3) 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 aza-Rh(II)-carbene is faster than oxy-Rh(II)-carbene.
多组分反应（Multi-component reactions, mcr）提供了一种通过在一个操作步骤中结合三种或三种以上的起始物质来构建多个化学键的有效方法，使快速、经济地合成结构多样的化合物成为可能。虽然羰基化合物（R-C:+）由于其独特的碳和碳正离子特性而显示出发展选择性mcs的潜力，但其在四组分反应（4cr）中的应用受到化学选择性挑战的限制。在此，我们提供了一个解决化学选择性4CR挑战的通用解决方案，使用halo重氮试剂作为类碳前体，然后依次与吡唑、醇和亚胺反应。这种方法允许在同一碳上同时构建三个不同的C (sp3)-N, C (sp3)-O和C (sp3)-C （sp3）键。该方案的成功主要取决于化学动力学的精确控制。详细的实验研究表明，aza-Rh(II)-carbene的生成速度比氧- rh (II)-carbene快。
{"title":"Chemo- and diastereoselective four-component reactions with Rh carbynoids","authors":"Mengchu Zhang , Xiaoyan Yang , Xiang Fu , Xiaoyu Zhou , Yu Qian , 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}
Pub Date : 2025-02-01Epub Date: 2024-10-03DOI: 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
Deuterium(D)-labelled organic compounds are used in many applications e.g., 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), e.g., 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.
{"title":"Sustainable synthetic routes to deuterium-labelled organic compounds using immobilized and recyclable (bio)catalysts","authors":"Luka Jedlovčnik , Jakob Höfferle , Aljaž Gaber , Fjoralb Pashaj , Jerneja Kladnik , Janez Košmrlj , Volker Derdau , 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}
Pub Date : 2025-02-01Epub Date: 2024-05-15DOI: 10.1016/j.gresc.2024.05.002
Heng Yang , Shuyu Yang , Xiao-Feng Wu , Feng Chen
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 β-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.
{"title":"Light-induced perfluoroalkylative carbonylation of unactivated alkenes with a recyclable photocatalyst","authors":"Heng Yang , Shuyu Yang , Xiao-Feng Wu , 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}
Pub Date : 2025-02-01Epub Date: 2024-10-05DOI: 10.1016/j.gresc.2024.09.006
Jieqing Wu , Liying Fu , Renyi Diao , Longjun Nie , Chi Zhang , Yufeng Li , Chao Feng
A novel approach to α-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.
{"title":"Sulfone as traceless activating group: Divergent synthesis of α-fluoroamides with C–F quaternary stereocenters","authors":"Jieqing Wu , Liying Fu , Renyi Diao , Longjun Nie , Chi Zhang , Yufeng Li , 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}
Pub Date : 2025-02-01Epub Date: 2023-09-29DOI: 10.1016/j.gresc.2023.09.003
Shumin Li, Jinke Chang, Jian Shen, Xiuling Cui
An efficient synthesis of indazole fused phenanthridinones via Rh(III)-catalyzed inert C(sp2)-H activation/[4 + 2] annulation of 3-aryl-1H-indazoles with iodonium ylides has been developed, providing a strategy to access multi-conjugated π-system tetracyclic and pentacyclic aza-heterocyclics with the favorable photoluminescence properties. This “one-pot” reaction features high efficiency, excellent regioselectivity, a broad substrate compatibility and could be easily scaled up. Furthermore, the obtained products exhibited low toxicity in MDCK cells as well as selectively labeled the zebrafish larvae, which indicated that the titled products could be potentially utilized as biofluorescent probes or fluorescent dyes.
{"title":"One-pot access to indazole fused-phenanthridinones via Rh(III)-catalyzed [4+2] annulation","authors":"Shumin Li, Jinke Chang, Jian Shen, Xiuling Cui","doi":"10.1016/j.gresc.2023.09.003","DOIUrl":"10.1016/j.gresc.2023.09.003","url":null,"abstract":"<div><div>An efficient synthesis of indazole fused phenanthridinones <em>via</em> Rh(III)-catalyzed inert C(sp<sup>2</sup>)-H activation/[4 + 2] annulation of 3-aryl-1<em>H</em>-indazoles with iodonium ylides has been developed, providing a strategy to access multi-conjugated π-system tetracyclic and pentacyclic aza-heterocyclics with the favorable photoluminescence properties. This “one-pot” reaction features high efficiency, excellent regioselectivity, a broad substrate compatibility and could be easily scaled up. Furthermore, the obtained products exhibited low toxicity in MDCK cells as well as selectively labeled the zebrafish larvae, which indicated that the titled products could be potentially utilized as biofluorescent probes or fluorescent dyes.</div></div>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"6 1","pages":"Pages 75-80"},"PeriodicalIF":0.0,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"134994561","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}
Pub Date : 2025-02-01Epub Date: 2024-11-09DOI: 10.1016/j.gresc.2024.11.001
Meng-Yao Li , Ao Gu , Jiatong Li , Yingbin Liu
The solvent-free and catalyst-free (SFCF) reaction has garnered significant interest among chemists due to its alignment with many of the 12 principles of green chemistry. In recent years, numerous innovative techniques have been employed to expand the scope of SFCF reactions and diversify the range of substrates. This paper presents an exhaustive examination of these transformations involving various functional groups, including alkenes, alkynes, aldehydes, ketones, imines, carboxylic acids, anhydrides, amides, amines, epoxides, aziridines, and organoselenides. Our review primarily seeks to elucidate the impact of solvent and concentration effects on these reactions by applying novel theories, such as the aggregate effect, multi-body effect, and multiple weak interactions, to ascertain how solvents impede these reactions. Additionally, different reaction mechanisms are contrasted under catalytic versus non-catalytic as well as solvent versus non-solvent conditions. Furthermore, the applications of such environmentally friendly reactions in fields such as material synthesis and drug synthesis are emphasized.
{"title":"Advanced green synthesis: Solvent-free and catalyst-free reaction","authors":"Meng-Yao Li , Ao Gu , Jiatong Li , Yingbin Liu","doi":"10.1016/j.gresc.2024.11.001","DOIUrl":"10.1016/j.gresc.2024.11.001","url":null,"abstract":"<div><div>The solvent-free and catalyst-free (SFCF) reaction has garnered significant interest among chemists due to its alignment with many of the 12 principles of green chemistry. In recent years, numerous innovative techniques have been employed to expand the scope of SFCF reactions and diversify the range of substrates. This paper presents an exhaustive examination of these transformations involving various functional groups, including alkenes, alkynes, aldehydes, ketones, imines, carboxylic acids, anhydrides, amides, amines, epoxides, aziridines, and organoselenides. Our review primarily seeks to elucidate the impact of solvent and concentration effects on these reactions by applying novel theories, such as the aggregate effect, multi-body effect, and multiple weak interactions, to ascertain how solvents impede these reactions. Additionally, different reaction mechanisms are contrasted under catalytic versus non-catalytic as well as solvent versus non-solvent conditions. Furthermore, the applications of such environmentally friendly reactions in fields such as material synthesis and drug synthesis are emphasized.</div></div>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"6 1","pages":"Pages 36-66"},"PeriodicalIF":0.0,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143508073","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}
Pub Date : 2025-02-01Epub Date: 2024-01-06DOI: 10.1016/j.gresc.2024.01.003
Ke-Li Wang, Hong-Tao Ji, Qiong-Hui Peng, Jun Jiang, Li-Juan Ou, Wei-Min He
With reusable sodium decatungstate (NaDT) as the photocatalyst, hydrocarbons (alkanes, ethers and ketones) as the alkylating agents, a wide range of alkylated fused N-heterocycles were obtained in high yield.
{"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":"10.1016/j.gresc.2024.01.003","url":null,"abstract":"<div><div>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.</div></div>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"6 1","pages":"Pages 106-109"},"PeriodicalIF":0.0,"publicationDate":"2025-02-01","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":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
The study of a Mitsunobu reaction is an important topic. Denton and co-workers first reported a novel (2-hydroxybenzyl)diphenylphosphine oxide for realizing the catalytic Mitsunobu reaction via a five-membered phosphonium species. However, it is still worth investigating how to improve catalysts with higher efficiency. Guided by computational and experimental studies, we designed a new type of biphenyl-based phosphine oxide that would form a six-membered phosphonium species as a key intermediate to trigger the catalytic Mitsunobu reaction with a lower barrier of the rate-determining step (30.3 kcal/mol). DFT calculations revealed that only trans dehydration was participated in our catalytic progress and a strong π-π interaction and small spatial constraint of TS-V were crucial for high behavior. This readily accessible, highly stable, easily recyclable and efficient catalyst would boost the catalytic Mitsunobu reaction.
{"title":"Development of a more efficient catalyst for the redox-neutral organocatalytic mitsunobu reaction by DFT-guided catalyst design","authors":"Dingguo Song , Changjun Zhang , Yuqi Cheng , Linlin Chen, Jie Lin, Changdi Zheng, Ting Liu, Yuxin Ding, Fei Ling, Weihui Zhong","doi":"10.1016/j.gresc.2023.11.002","DOIUrl":"10.1016/j.gresc.2023.11.002","url":null,"abstract":"<div><div>The study of a Mitsunobu reaction is an important topic. Denton and co-workers first reported a novel (2-hydroxybenzyl)diphenylphosphine oxide for realizing the catalytic Mitsunobu reaction <em>via</em> a five-membered phosphonium species. However, it is still worth investigating how to improve catalysts with higher efficiency. Guided by computational and experimental studies, we designed a new type of biphenyl-based phosphine oxide that would form a six-membered phosphonium species as a key intermediate to trigger the catalytic Mitsunobu reaction with a lower barrier of the rate-determining step (30.3 kcal/mol). DFT calculations revealed that only trans dehydration was participated in our catalytic progress and a strong <em>π</em>-<em>π</em> interaction and small spatial constraint of <strong>TS-V</strong> were crucial for high behavior. This readily accessible, highly stable, easily recyclable and efficient catalyst would boost the catalytic Mitsunobu reaction.</div></div>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"5 4","pages":"Pages 290-296"},"PeriodicalIF":0.0,"publicationDate":"2024-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135715435","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}
Pub Date : 2024-11-01Epub Date: 2023-09-20DOI: 10.1016/j.gresc.2023.09.002
Jinjin Chen , Pingyu Jiang , Xinping Liu , Huawen Huang , Guojiang Mao , Guo-Jun Deng
The Pictet-Spengler/transamination cascade reaction enables modular synthesis of marinoquinoline analogues through three-component indole ring-expansion/cyclization in the manner of novel N1–C2 cleavage of indoles. This metal-free protocol exhibits very broad functional group tolerance with up to quantitative yields. Preliminary studies on the antitumor activity of the resultant marinoquinoline analogues reveal that the indolyl-attached pyrrolo[2,3-c]quinoline product (5d) shows great potential (IC50 of 0.32 μg/mL to HeLa cells) as a promising anticancer agent in clinic.
{"title":"Pictet-spengler/transamination cascade reaction of indoles for modular synthesis of marinoquinoline analogues","authors":"Jinjin Chen , Pingyu Jiang , Xinping Liu , Huawen Huang , Guojiang Mao , Guo-Jun Deng","doi":"10.1016/j.gresc.2023.09.002","DOIUrl":"10.1016/j.gresc.2023.09.002","url":null,"abstract":"<div><div>The Pictet-Spengler/transamination cascade reaction enables modular synthesis of marinoquinoline analogues through three-component indole ring-expansion/cyclization in the manner of novel N1–C2 cleavage of indoles. This metal-free protocol exhibits very broad functional group tolerance with up to quantitative yields. Preliminary studies on the antitumor activity of the resultant marinoquinoline analogues reveal that the indolyl-attached pyrrolo[2,3-<em>c</em>]quinoline product (<strong>5d</strong>) shows great potential (IC<sub>50</sub> of 0.32 μg/mL to HeLa cells) as a promising anticancer agent in clinic.</div></div>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"5 4","pages":"Pages 310-314"},"PeriodicalIF":0.0,"publicationDate":"2024-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135388295","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}
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