Zhenhui Wang, Qianqian Yang, Lan Bao, Ruiyun Zhang, Mingming Gao, wei liu
Herein, we present an efficient photoinduced copper-catalyzed N-arylation reaction occurring through the cross-coupling of N–H heteroarene with aryl thianthrenium salt (Ar-TTs). This photoactivation strategy exhibits a broad substrate scope, and offers a method for preserving the activated functional groups (such as Br, CHO, and CN) for subsequent derivatizations.
{"title":"Photoinduced Copper-Catalyzed N-Arylation Reaction of N–H Heteroarenes Using Aryl Thianthrenium Salts","authors":"Zhenhui Wang, Qianqian Yang, Lan Bao, Ruiyun Zhang, Mingming Gao, wei liu","doi":"10.1002/ejoc.202500303","DOIUrl":"https://doi.org/10.1002/ejoc.202500303","url":null,"abstract":"Herein, we present an efficient photoinduced copper-catalyzed N-arylation reaction occurring through the cross-coupling of N–H heteroarene with aryl thianthrenium salt (Ar-TTs). This photoactivation strategy exhibits a broad substrate scope, and offers a method for preserving the activated functional groups (such as Br, CHO, and CN) for subsequent derivatizations.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"71 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-04-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143862646","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Georges Massiot, Fadila Derguini, Flavien Marcadet, Fabien Plisson, Raphael Rahmani, Florie Lavigne, Christophe Menendez, Christophe Long
Tagitinin C, a germacranolide, isolated from Tithonia diversifolia was shown to have an interesting level of activity on the proteasome pathway. It is however a particularly unstable molecule, sensitive to acids, bases, nucleophiles, and light. This article describes a series of modifications aimed at improving the chemical and biological properties of the molecule and securing a solid industrial property. This study particularly focuses on the isobutyrate chain replacement by other esters or ethers. The key steps were the cross-conjugated dienone reactivity neutralization by reduction and the methylene lactone protection with morpholine or imidazole. Selective saponification of the isobutyrate was also achieved with crude pig liver esterase leading to tagitinol C with a moderate yield. Heliangine from the Jerusalem artichoke (Helianthus tuberosus) and hydroxylated derivatives of tagitinin C from the common sunflower (Helianthus annuus), two abundant field crops, constituted alternative sources of germacranolide derivatives not accessible from tagitinin C. Some esters were more potent than the lead compound, whereas the di-ethers displayed higher activity levels, probably due to a better in vivo stability.
{"title":"Tagitinin C, a Sesquiterpene Lactone, and Derivatives as Proteasome Inhibitors","authors":"Georges Massiot, Fadila Derguini, Flavien Marcadet, Fabien Plisson, Raphael Rahmani, Florie Lavigne, Christophe Menendez, Christophe Long","doi":"10.1002/ejoc.202500181","DOIUrl":"https://doi.org/10.1002/ejoc.202500181","url":null,"abstract":"Tagitinin C, a germacranolide, isolated from Tithonia diversifolia was shown to have an interesting level of activity on the proteasome pathway. It is however a particularly unstable molecule, sensitive to acids, bases, nucleophiles, and light. This article describes a series of modifications aimed at improving the chemical and biological properties of the molecule and securing a solid industrial property. This study particularly focuses on the isobutyrate chain replacement by other esters or ethers. The key steps were the cross-conjugated dienone reactivity neutralization by reduction and the methylene lactone protection with morpholine or imidazole. Selective saponification of the isobutyrate was also achieved with crude pig liver esterase leading to tagitinol C with a moderate yield. Heliangine from the Jerusalem artichoke (Helianthus tuberosus) and hydroxylated derivatives of tagitinin C from the common sunflower (Helianthus annuus), two abundant field crops, constituted alternative sources of germacranolide derivatives not accessible from tagitinin C. Some esters were more potent than the lead compound, whereas the di-ethers displayed higher activity levels, probably due to a better in vivo stability.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"2 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-04-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143858150","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
M.Sc. Julian Friedrich, Dr. Marc Schmidtmann, Prof. Dr. Jens Christoffers
The Front Cover shows two dwarves digging for rare minerals and gemstones in a mine. They are excited when they find crystals of bi- and tricyclic diketones and lactones. The cover image suggests that these very rare structures have crystallized over millions of years in incredible geochemical processes. In contrast to this myth, the products have now been synthesized by manganese-catalyzed oxidative radical cyclizations in an aerobic atmosphere. More information can be found in the Research Article by J. Christoffers and co-workers (DOI: 10.1002/ejoc.202500158). Artwork by Amelie Christoffers.
{"title":"Front Cover: Investigations into Intramolecular Cerium- and Manganese-Catalyzed Aerobic Coupling of β-Oxoesters with Styryl Moieties (Eur. J. Org. Chem. 15/2025)","authors":"M.Sc. Julian Friedrich, Dr. Marc Schmidtmann, Prof. Dr. Jens Christoffers","doi":"10.1002/ejoc.202581501","DOIUrl":"https://doi.org/10.1002/ejoc.202581501","url":null,"abstract":"<p><b>The Front Cover</b> shows two dwarves digging for rare minerals and gemstones in a mine. They are excited when they find crystals of bi- and tricyclic diketones and lactones. The cover image suggests that these very rare structures have crystallized over millions of years in incredible geochemical processes. In contrast to this myth, the products have now been synthesized by manganese-catalyzed oxidative radical cyclizations in an aerobic atmosphere. More information can be found in the Research Article by J. Christoffers and co-workers (DOI: 10.1002/ejoc.202500158). Artwork by Amelie Christoffers.\u0000 <figure>\u0000 <div><picture>\u0000 <source></source></picture><p></p>\u0000 </div>\u0000 </figure>\u0000 </p>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 15","pages":""},"PeriodicalIF":2.5,"publicationDate":"2025-04-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ejoc.202581501","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143861691","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Herein, we report a one-pot synthesis of 3,4-dihydropyridin-2(H)-one containing thiazole derivatives by Bronsted acid-mediated ring-rearrangement and formal (3+2) cycloaddition reaction of enaminone-based thioalkyne with alkyl/aryl nitrile. The developed protocol demonstrates a wide substrate scope for both the reacting partners with high atom-economy furnishing very high to excellent yields of pharmaceutically relevant bis-heterocyclic derivatives. Based on outcome of the product and control experiments, a plausible reaction mechanism has also been proposed. The gram-scale synthesis and further synthetic transformation demonstrate the synthetic efficacy and utility of the developed protocol.
{"title":"Ring-Rearrangement-Driven Formal (3+2) Cycloaddition of Enaminone-Based Thioalkynes with Nitriles to Form Thiazole-Containing Bis-heterocycles","authors":"Chandran R, Abha Sharma, Keshri Nath Tiwari","doi":"10.1002/ejoc.202500287","DOIUrl":"https://doi.org/10.1002/ejoc.202500287","url":null,"abstract":"Herein, we report a one-pot synthesis of 3,4-dihydropyridin-2(H)-one containing thiazole derivatives by Bronsted acid-mediated ring-rearrangement and formal (3+2) cycloaddition reaction of enaminone-based thioalkyne with alkyl/aryl nitrile. The developed protocol demonstrates a wide substrate scope for both the reacting partners with high atom-economy furnishing very high to excellent yields of pharmaceutically relevant bis-heterocyclic derivatives. Based on outcome of the product and control experiments, a plausible reaction mechanism has also been proposed. The gram-scale synthesis and further synthetic transformation demonstrate the synthetic efficacy and utility of the developed protocol.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"7 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-04-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143858125","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
In the last 20 years the exploitation of antioxidant activity of selenobased compounds has improved, just due to the use of Ebselen, a selenocompound, as a Glutathione peroxidase (GPx) mimic. However, their clinical use seems to be compromised by the low solubility in water. To deal with this problem is possible to take advantage of the new approach including selenosugars in which selenium replaces heterocyclic oxygen. In this frame, to optimize the antioxidant properties of selenosugars, the glycoconjugation with a polyphenolic unit, which is a molecule capable of inhibiting or disabling the action of free radicals, has been considered in this work. The Mitsunobu reaction mechanism links covalently the primary alcoholic function of selenobased glycosyl donors, coming from the commercially available d-mannose, and phenolic moiety acceptors, to obtain the corresponding glycoconjugates, has been exploited affording the products in efficient yields. A DFT theoretical study was carried out to help understand the possible influence of the seleno donor on the reactivity. Crucially, a new pathway based on Pummerer-like rearrangement followed by a glycosylation, gave a selenosugar with selenium in the ring and bearing an acetal-like functional group at C-1. All compounds were characterized by NMR spectroscopy confirming their structures and purity.
{"title":"New Glycoconjugates Containing Selenium and Polyphenols. Stereoselective Synthesis by Pummerer-like Rearrangement","authors":"Claudia González, Mauro De Nisco, Reinier Lemos, Giovanna Cimmino, Yoana Pérez-Badell, Severina Pacifico, Silvana Pedatella","doi":"10.1002/ejoc.202500291","DOIUrl":"https://doi.org/10.1002/ejoc.202500291","url":null,"abstract":"In the last 20 years the exploitation of antioxidant activity of selenobased compounds has improved, just due to the use of Ebselen, a selenocompound, as a Glutathione peroxidase (GPx) mimic. However, their clinical use seems to be compromised by the low solubility in water. To deal with this problem is possible to take advantage of the new approach including selenosugars in which selenium replaces heterocyclic oxygen. In this frame, to optimize the antioxidant properties of selenosugars, the glycoconjugation with a polyphenolic unit, which is a molecule capable of inhibiting or disabling the action of free radicals, has been considered in this work. The Mitsunobu reaction mechanism links covalently the primary alcoholic function of selenobased glycosyl donors, coming from the commercially available d-mannose, and phenolic moiety acceptors, to obtain the corresponding glycoconjugates, has been exploited affording the products in efficient yields. A DFT theoretical study was carried out to help understand the possible influence of the seleno donor on the reactivity. Crucially, a new pathway based on Pummerer-like rearrangement followed by a glycosylation, gave a selenosugar with selenium in the ring and bearing an acetal-like functional group at C-1. All compounds were characterized by NMR spectroscopy confirming their structures and purity.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 7 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-04-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143849458","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
An efficient catalyst‐free, solvent‐free amination reaction has been developed for the synthesis of various bio‐inspired 6‐substituted amino purine nucleoside analogues in good yields. In this sustainable approach, unprotected 6‐substituted aminopurine nucleoside analogues were synthesized via amination reactions of unprotected 6‐Cl purine nucleosides with various amine derivatives. Notably, this method offers a simple, eco‐friendly, unifying protocol for the synthesis of various bioinspired molecules with highly functional group tolerance. Additionally, to demonstrate its synthetic applicability, a one‐pot, three‐component reaction protocol has been shown for the synthesis of novel 1,2,3‐triazole‐attached hybrid nucleoside containing various drug core moieties via click chemistry.
{"title":"An Efficient Solvent‐Free, Catalyst‐Free Amination on Modified Nucleosides and One‐Pot Three‐Component Synthesis of 1,2,3‐Triazole‐Based Hybrid Nucleosides","authors":"Samir Kumar Mondal, Shantanu Pal","doi":"10.1002/ejoc.202500203","DOIUrl":"https://doi.org/10.1002/ejoc.202500203","url":null,"abstract":"An efficient catalyst‐free, solvent‐free amination reaction has been developed for the synthesis of various bio‐inspired 6‐substituted amino purine nucleoside analogues in good yields. In this sustainable approach, unprotected 6‐substituted aminopurine nucleoside analogues were synthesized via amination reactions of unprotected 6‐Cl purine nucleosides with various amine derivatives. Notably, this method offers a simple, eco‐friendly, unifying protocol for the synthesis of various bioinspired molecules with highly functional group tolerance. Additionally, to demonstrate its synthetic applicability, a one‐pot, three‐component reaction protocol has been shown for the synthesis of novel 1,2,3‐triazole‐attached hybrid nucleoside containing various drug core moieties via click chemistry.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"29 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-04-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143842002","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Yan Yu, Xin Wang, Yicheng Zhang, Kuai Wang, Ling-Guo Meng
Conventional synthetic routes to benzofused oxygenated heterocycles, such as Dihydrobenzofuran, chromane and isochromane derivatives, often involve complex synthetic conditions, high costs, and environmental concerns. The key to addressing this challenge lies in achieving transition‐metal‐free C(sp²)–I bond cleavage to enable intramolecular radical cyclization. Inspired by electroreductive strategies, we developed a convenient, transition‐metal‐free electroreductive tandem reaction for synthesizing dihydrobenzofuran, chromane, and isochromane derivatives. Comprehensive evaluation demonstrates that our approach not only simplifies synthetic conditions but also suppresses competing hydrogenation and halogenation pathways at the exocyclic carbon radical center.
{"title":"Electroreductive Intramolecular Heck‐Type Cyclization for the Synthesis of Benzofused Oxygenated Heterocycles","authors":"Yan Yu, Xin Wang, Yicheng Zhang, Kuai Wang, Ling-Guo Meng","doi":"10.1002/ejoc.202500222","DOIUrl":"https://doi.org/10.1002/ejoc.202500222","url":null,"abstract":"Conventional synthetic routes to benzofused oxygenated heterocycles, such as Dihydrobenzofuran, chromane and isochromane derivatives, often involve complex synthetic conditions, high costs, and environmental concerns. The key to addressing this challenge lies in achieving transition‐metal‐free C(sp²)–I bond cleavage to enable intramolecular radical cyclization. Inspired by electroreductive strategies, we developed a convenient, transition‐metal‐free electroreductive tandem reaction for synthesizing dihydrobenzofuran, chromane, and isochromane derivatives. Comprehensive evaluation demonstrates that our approach not only simplifies synthetic conditions but also suppresses competing hydrogenation and halogenation pathways at the exocyclic carbon radical center.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"14 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-04-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143842003","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Anna Lena Opper, Xin Nie, Sergei I. Ivlev, Eric Meggers
A ruthenium-catalyzed C(sp3)H carbene insertion leads to the enantioselective formation of chiral β-lactams in up to 82% isolated yield and excellent enantioselectivities up to 98% enantiomeric excess without any indication of a competing Buchner reaction. The reaction is catalyzed by a new ruthenium complex containing a chiral pyridine-2,6-bis(oxazoline) ligand in combination with a cyclometalated phenylimidazo[1,5-a]pyridine ligand.
{"title":"Chiral β-Lactams by Ruthenium-Catalyzed Enantioselective C?H Carbene Insertion","authors":"Anna Lena Opper, Xin Nie, Sergei I. Ivlev, Eric Meggers","doi":"10.1002/ejoc.202500076","DOIUrl":"https://doi.org/10.1002/ejoc.202500076","url":null,"abstract":"A ruthenium-catalyzed C(sp<sup>3</sup>)<b><span></span></b>H carbene insertion leads to the enantioselective formation of chiral β-lactams in up to 82% isolated yield and excellent enantioselectivities up to 98% enantiomeric excess without any indication of a competing Buchner reaction. The reaction is catalyzed by a new ruthenium complex containing a chiral pyridine-2,6-bis(oxazoline) ligand in combination with a cyclometalated phenylimidazo[1,5-<i>a</i>]pyridine ligand.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"20 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-04-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143836955","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Amides derived from common hydroxycinnamic acids — including 4-hydroxycinnamic acid, 3-methoxy-4-hydroxycinnamic acid, 3,4-dihydroxycinnamic acid, 3,4-dimethoxycinnamic acid, and 3,4,5-trimethoxycinnamic acid — along with various free aminobenzoic acids, such as 5-hydroxy-2-aminobenzoic acid, a key component of the avenanthramide family, have been rapidly synthesized using an innovative, environmentally friendly synthetic methodology. This approach, grounded in traditional chemistry, utilizes mixed anhydrides to simultaneously protect and activate hydroxycinnamic acids through the actions of triethylamine and isobutyl chloroformate while employing acetone as a green solvent. The resulting amides, formed from the coupling with free aromatic amino acids, are constructed as O-carbonate-protected derivatives with high yields and purity, isolated directly via crystallization, thus eliminating chromatographic or HPLC purifications. Furthermore, free phenols can be conveniently released on demand using morpholine in methanol. Under these conditions, C-protected aromatic amino acids remain unacylated. This synthetic strategy represents a significant advancement over conventional acyl chloride methodologies, which often rely on toxic reagents and solvents and entail time-consuming and complex procedures. It enhances the production of important phytochemicals such as Avenanthramides and opens doors to various analogs, paving the way for potential pharmacological applications.
{"title":"Improved Chemical Synthesis of Avenanthramides Family and its Analogs by Mixed Anhydride Method","authors":"Armando Zarrelli, Luigi Longobardo","doi":"10.1002/ejoc.202500169","DOIUrl":"https://doi.org/10.1002/ejoc.202500169","url":null,"abstract":"Amides derived from common hydroxycinnamic acids — including 4-hydroxycinnamic acid, 3-methoxy-4-hydroxycinnamic acid, 3,4-dihydroxycinnamic acid, 3,4-dimethoxycinnamic acid, and 3,4,5-trimethoxycinnamic acid — along with various free aminobenzoic acids, such as 5-hydroxy-2-aminobenzoic acid, a key component of the avenanthramide family, have been rapidly synthesized using an innovative, environmentally friendly synthetic methodology. This approach, grounded in traditional chemistry, utilizes mixed anhydrides to simultaneously protect and activate hydroxycinnamic acids through the actions of triethylamine and isobutyl chloroformate while employing acetone as a green solvent. The resulting amides, formed from the coupling with free aromatic amino acids, are constructed as O-carbonate-protected derivatives with high yields and purity, isolated directly via crystallization, thus eliminating chromatographic or HPLC purifications. Furthermore, free phenols can be conveniently released on demand using morpholine in methanol. Under these conditions, C-protected aromatic amino acids remain unacylated. This synthetic strategy represents a significant advancement over conventional acyl chloride methodologies, which often rely on toxic reagents and solvents and entail time-consuming and complex procedures. It enhances the production of important phytochemicals such as Avenanthramides and opens doors to various analogs, paving the way for potential pharmacological applications.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"53 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-04-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143836961","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Hai Dong, Jian Lv, Chun-Yang Liu, Xiaorui Zhang, Shuang-Xi Gu
Phosphorylated molecules, particularly phosphorylated carbohydrates, have garnered significant interest due to their distinct biological activities, driving an urgent demand for efficient phosphorylation strategies. In this study, we demonstrate the successful development of a SnCl2-catalyzed protocol for the phosphorylation of alcohols and carbohydrates. Notably, the reaction efficiency was found to be critically dependent on the addition order of SnCl2 and N,N-diisopropylethylamine, a phenomenon systematically investigated through mechanistic studies. A one-pot sequential ketalization/phosphorylation strategy was established for polyol substrates, enabling streamlined access to phosphorylated derivatives. The versatility of this approach was further exemplified by achieving selective phosphorylation/phosphinoylation of carbohydrates.
{"title":"SnCl2-Catalyzed Phosphorylation of Alcohols and Selective Phosphorylation/Phosphinoylation of Carbohydrates","authors":"Hai Dong, Jian Lv, Chun-Yang Liu, Xiaorui Zhang, Shuang-Xi Gu","doi":"10.1002/ejoc.202500209","DOIUrl":"https://doi.org/10.1002/ejoc.202500209","url":null,"abstract":"Phosphorylated molecules, particularly phosphorylated carbohydrates, have garnered significant interest due to their distinct biological activities, driving an urgent demand for efficient phosphorylation strategies. In this study, we demonstrate the successful development of a SnCl2-catalyzed protocol for the phosphorylation of alcohols and carbohydrates. Notably, the reaction efficiency was found to be critically dependent on the addition order of SnCl2 and N,N-diisopropylethylamine, a phenomenon systematically investigated through mechanistic studies. A one-pot sequential ketalization/phosphorylation strategy was established for polyol substrates, enabling streamlined access to phosphorylated derivatives. The versatility of this approach was further exemplified by achieving selective phosphorylation/phosphinoylation of carbohydrates.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"26 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-04-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143836962","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
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