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 , 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}
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 , 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}
{"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}
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 , 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}
{"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}
{"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}
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":"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}
{"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}
Jinjin Chen , Pingyu Jiang , Xinping Liu , Huawen Huang , Guojiang Mao , Guo-Jun Deng
{"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}
Yanyan Que , Wenli Lei , Yin Fang , Shuzhong He , Yang Chen
{"title":"Recent advances in (4 + 3) cycloaddition of allenes","authors":"Yanyan Que , Wenli Lei , Yin Fang , Shuzhong He , Yang Chen","doi":"10.1016/j.gresc.2023.11.010","DOIUrl":"10.1016/j.gresc.2023.11.010","url":null,"abstract":"<div><div>Allenes are a class of unsaturated compounds containing a propadiene structural moiety, exhibiting essential physiological, pharmacological, and various reactivities. Their (4 + 3) cycloaddition reaction has become an effective method for synthesizing seven-membered rings, especially for heterocycles. This method has been continuously improved and developed. Herein, we review the (4 + 3) cycloaddition of allenes, focusing on the developed methodologies and the outlook in this field from 2013 to 2023.</div></div>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"5 4","pages":"Pages 270-276"},"PeriodicalIF":0.0,"publicationDate":"2024-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138543705","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}