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Temperature-Dependent Regiodivergent Synthesis of Functionalized Maleimides and Itaconimides via in-situ Generated Pyridinium Ylide
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-02-26 DOI: 10.1002/ejoc.202401448
Suman Kumar Saha, Anupriya Bera, Akanksha Kumari, Mahesh Loitongbam, Debjyoti Chakladar, Nirmal K Rana
{"title":"Temperature-Dependent Regiodivergent Synthesis of Functionalized Maleimides and Itaconimides via in-situ Generated Pyridinium Ylide","authors":"Suman Kumar Saha, Anupriya Bera, Akanksha Kumari, Mahesh Loitongbam, Debjyoti Chakladar, Nirmal K Rana","doi":"10.1002/ejoc.202401448","DOIUrl":"https://doi.org/10.1002/ejoc.202401448","url":null,"abstract":"We report a temperature-dependent regiodivergent synthetic strategy for the construction of functionalized maleimides and itaconimides using in-situ generated pyridinium ylides. This approach enables efficient access to both regioisomeric products under mild and straightforward reaction conditions. A variety of pyridinium salts with different aromatic and alkyl groups were successfully used with N-aryl and N-alkyl succinimides demonstrating broad substrate compatibility. The practicality and scalability of this methodology were confirmed through scale-up experiments, which maintained high yields and reproducibility.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"187 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-02-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143496176","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}
引用次数: 0
Photocarboxylation of Arylated 2H-Azirines Exploiting Continuous Flow Technology
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-02-26 DOI: 10.1002/ejoc.202500177
Arlene Bonner, Jorge García-Lacuna, Marcus Baumann
{"title":"Photocarboxylation of Arylated 2H-Azirines Exploiting Continuous Flow Technology","authors":"Arlene Bonner, Jorge García-Lacuna, Marcus Baumann","doi":"10.1002/ejoc.202500177","DOIUrl":"https://doi.org/10.1002/ejoc.202500177","url":null,"abstract":"A robust and efficient continuous flow set-up is presented for the orchestrated use of CO2 gas and photochemistry in flow mode. This study explores the catalyst-free cycloaddition between azomethine ylides generated in situ from simple 2H-azirines and CO2. Using UV-A light (365 nm) as energy source and CO2 as inexpensive and abundant building block provides an attractive strategy affording isomeric oxazolones which were subsequently aromatised to yield novel oxazole products in a convergent manner. Continuous flow processing substantially improves the reaction performance allowing for the safe exploitation of this intriguing transformation. This enables the effective fixation of CO2 to generate valuable building blocks that can be scaled to gram scale with ease.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"10 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-02-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143496177","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}
引用次数: 0
Blue-light-driven iron-catalyzed desulfurization of thioamides under hydrosilylation conditions
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-02-26 DOI: 10.1002/ejoc.202500048
Qingxin ZHANG, Christophe Darcel
{"title":"Blue-light-driven iron-catalyzed desulfurization of thioamides under hydrosilylation conditions","authors":"Qingxin ZHANG, Christophe Darcel","doi":"10.1002/ejoc.202500048","DOIUrl":"https://doi.org/10.1002/ejoc.202500048","url":null,"abstract":"Up to now, there were only few reports on Earth-abundant transition metal catalyzed reduction of thioamides, one of the explanation of this scarcity being the possible metallic catalyst poisoning due to the adsorption of species containing sulfur. In this contribution, we report the first general iron-catalyzed hydrogenative desulfurization of tertiary thioamides under hydrosilylation conditions at ambient temperature, the reaction being driven by blue light irradiation. To perform selectively the reduction of thioamides leading to amines (30 examples, 29-97% yields), highlighting the sole cleavage of the C=S bond, Fe(IMes)(CO)4 catalyst was used in the presence of phenylsilane under ambient conditions","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-02-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143496175","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}
引用次数: 0
Metal‐Free Direct Synthesis of Secondary Amides and Nitriles Using O‐(2‐Pyrimidinyl)‐N‐Boc Hydroxylamine 用O‐（2‐嘧啶基）‐N‐Boc羟胺直接合成仲酰胺和腈
IF 2.5 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-02-24 DOI: 10.1002/ejoc.202401229
Ashirwad Divedi , Dr. Saumya Verma , Dr. Dinesh Chandra , Shivam Bhargav , Ved Prakash Verma , Dr. Jawahar L. Jat
{"title":"Metal‐Free Direct Synthesis of Secondary Amides and Nitriles Using O‐(2‐Pyrimidinyl)‐N‐Boc Hydroxylamine","authors":"Ashirwad Divedi ,&nbsp;Dr. Saumya Verma ,&nbsp;Dr. Dinesh Chandra ,&nbsp;Shivam Bhargav ,&nbsp;Ved Prakash Verma ,&nbsp;Dr. Jawahar L. Jat","doi":"10.1002/ejoc.202401229","DOIUrl":"10.1002/ejoc.202401229","url":null,"abstract":"<div><div>A novel hydroxylamine‐derived aminating agent, <em>O</em>‐(2‐pyrimidinyl)‐<em>N</em>‐Boc hydroxylamine (PymONHBoc), has been designed and synthesized, from readily available 2‐chloropyrimidine. This reagent demonstrates superior shelf stability and ease of handling compared to other hydroxylamine‐derived reagents. Here, we present a metal‐free method for the direct conversion of ketones and aldehydes into sec‐amides and nitriles using PymONHBoc as the aminating agent. This method efficiently converts a wide range of aliphatic and aromatic carbonyl compounds into the corresponding amides and nitriles with good to excellent yields under ambient conditions. The use of PymONHBoc is advantageous, as it facilitates the in situ generation of the activated oxime intermediate, concomitantly producing a non‐interfering byproduct.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 8","pages":"Article e202401229"},"PeriodicalIF":2.5,"publicationDate":"2025-02-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142888035","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}
引用次数: 0
Synthesis of Benzoxazoles by Metal‐Free Oxidative Cyclization of Catechols with Amines
IF 2.5 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-02-24 DOI: 10.1002/ejoc.202401281
Feng Liu , Wan Wang , Dr. Jianyu Dong , Dr. Shaofeng Wu , Dr. Lebin Su , Prof. Dr. Yongbo Zhou
{"title":"Synthesis of Benzoxazoles by Metal‐Free Oxidative Cyclization of Catechols with Amines","authors":"Feng Liu ,&nbsp;Wan Wang ,&nbsp;Dr. Jianyu Dong ,&nbsp;Dr. Shaofeng Wu ,&nbsp;Dr. Lebin Su ,&nbsp;Prof. Dr. Yongbo Zhou","doi":"10.1002/ejoc.202401281","DOIUrl":"10.1002/ejoc.202401281","url":null,"abstract":"<div><div>Benzoxazoles are crucial in pharmaceuticals, agrochemicals, and functional materials. Their simple, economical, green, and efficient synthesis has attracted long‐standing interest in synthetic chemistry. Herein, we present an extremely simple strategy for constructing benzoxazoles via the direct oxidative cyclization of readily available catechols and primary amines, using DDQ/EA and O₂/water oxidative systems, respectively. The DDQ/EA system demonstrates distinct advantages in substrate and functional group compatibility. In contrast, the O₂/water system, which is milder, greener, and more economical, excels in synthesizing C‐2 alkyl‐substituted benzoxazoles. Overall, these two systems provide complementary advantages and are both well‐suited for gram‐scale synthesis. Given its high simplicity and practicality, this strategy could serve as a promising alternative in benzoxazole synthesis.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 8","pages":"Article e202401281"},"PeriodicalIF":2.5,"publicationDate":"2025-02-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143258796","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}
引用次数: 0
Recent Advances in Sustainable Total Synthesis and Chiral Pool Strategies with Emphasis on (−)‐Sclareol in Natural Products Synthesis 以天然产品合成中的 (-)-Sclareol 为重点的可持续全合成和手性池策略的最新进展
IF 2.5 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-02-24 DOI: 10.1002/ejoc.202400983
Ayyoub Selka , Abdelnasser Abidli , Lucie Schiavo , Loïc Jeanmart , Gilles Hanquet , William D. Lubell
{"title":"Recent Advances in Sustainable Total Synthesis and Chiral Pool Strategies with Emphasis on (−)‐Sclareol in Natural Products Synthesis","authors":"Ayyoub Selka ,&nbsp;Abdelnasser Abidli ,&nbsp;Lucie Schiavo ,&nbsp;Loïc Jeanmart ,&nbsp;Gilles Hanquet ,&nbsp;William D. Lubell","doi":"10.1002/ejoc.202400983","DOIUrl":"10.1002/ejoc.202400983","url":null,"abstract":"<div><div>Starting materials for sustainable total synthesis often come from the chiral pool: carbohydrates, cyclitols, amino acids, and terpenes. In the terpene family, (−)‐sclareol has served as a sustainable, readily available, and versatile chiral building block for the synthesis of numerous natural products. (−)‐Sclareol possesses a unique structure that has consequently promoted its integration as a core framework within various structurally complex and biologically active substances, including sesquiterpenoids, diterpenoids, and sesterterpenoids. (−)‐Sclareol has facilitated access to diverse synthetic key intermediates, promoting the sustainable synthesis of several natural products. Herein, a review is presented covering the recent trends in sustainable total syntheses and the application of chiral pool approaches with emphasis on the preparation of natural products through diverse routes employing (−)‐sclareol as chiral educt. Innovative catalytic and synthetic protocols using (−)‐sclareol are also analyzed and discussed.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 8","pages":"Article e202400983"},"PeriodicalIF":2.5,"publicationDate":"2025-02-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ejoc.202400983","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142805136","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}
引用次数: 0
Rhodium(III)‐Catalyzed [4+2] Annulation of N‐Hydroxyoximes with Maleate Esters/2‐Chloroacrylates: Synthesis of Isoquinoline‐3,4‐Dicarboxylates and Isoquinoline‐3‐Carboxylates 铑（III）催化的N -羟基肟与马来酸酯/2 -氯丙烯酸酯的[4+2]环化反应：异喹啉- 3,4 -二羧酸和异喹啉- 3 -羧酸的合成
IF 2.5 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-02-24 DOI: 10.1002/ejoc.202401264
He Li , Tao Chen , Zhiwei Wang , Yuxin Li , Baoheng Wu , Ning Xu , Ye Lu , Xinxin Jin , Jiaqi Yu , Jinglin Liu , Ming Bao
{"title":"Rhodium(III)‐Catalyzed [4+2] Annulation of N‐Hydroxyoximes with Maleate Esters/2‐Chloroacrylates: Synthesis of Isoquinoline‐3,4‐Dicarboxylates and Isoquinoline‐3‐Carboxylates","authors":"He Li ,&nbsp;Tao Chen ,&nbsp;Zhiwei Wang ,&nbsp;Yuxin Li ,&nbsp;Baoheng Wu ,&nbsp;Ning Xu ,&nbsp;Ye Lu ,&nbsp;Xinxin Jin ,&nbsp;Jiaqi Yu ,&nbsp;Jinglin Liu ,&nbsp;Ming Bao","doi":"10.1002/ejoc.202401264","DOIUrl":"10.1002/ejoc.202401264","url":null,"abstract":"<div><div>A novel Rh(III)‐catalyzed [4+2] annulation of <em>N</em>‐hydroxyoximes with maleate esters/2‐chloroacrylates is disclosed, in which diverse isoquinoline skeleton compounds were generated in moderate to excellent yields. The protocol exhibits a good compatibility of functional groups and wide scope of substrates without using any external metal oxidants. Gram‐scale and derivatization reactions were performed to show the potential utility of this transformation.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 8","pages":"Article e202401264"},"PeriodicalIF":2.5,"publicationDate":"2025-02-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142888094","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}
引用次数: 0
Synthesis of Chiral Heterocycles Through Enantioselective Silver‐Catalyzed Transformations 对映选择性银催化转化合成手性杂环化合物
IF 2.5 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-02-24 DOI: 10.1002/ejoc.202401284
Dr. Hélène Pellissier
{"title":"Synthesis of Chiral Heterocycles Through Enantioselective Silver‐Catalyzed Transformations","authors":"Dr. Hélène Pellissier","doi":"10.1002/ejoc.202401284","DOIUrl":"10.1002/ejoc.202401284","url":null,"abstract":"<div><div>This review collects the recent developments in the synthesis of chiral heterocycles through enantioselective silver‐catalyzed transformations published since 2018. It demonstrates the power of chiral silver catalysts as special mild Lewis acids to provide an impressive diversity of reaction pathways, such as 1,3‐dipolar cycloadditions, various types of cyclizations, along with a wide variety of more complex domino/tandem reactions, allowing many types of novel chiral heterocyclic products to be achieved in high enantioselectivities.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 8","pages":"Article e202401284"},"PeriodicalIF":2.5,"publicationDate":"2025-02-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142911892","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}
引用次数: 0
Front Cover: Recent Advances in Sustainable Total Synthesis and Chiral Pool Strategies with Emphasis on (−)-Sclareol in Natural Products Synthesis (Eur. J. Org. Chem. 8/2025)
IF 2.5 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-02-24 DOI: 10.1002/ejoc.202580801
Ayyoub Selka, Abdelnasser Abidli, Lucie Schiavo, Loïc Jeanmart, Gilles Hanquet, William D. Lubell
{"title":"Front Cover: Recent Advances in Sustainable Total Synthesis and Chiral Pool Strategies with Emphasis on (−)-Sclareol in Natural Products Synthesis (Eur. J. Org. Chem. 8/2025)","authors":"Ayyoub Selka,&nbsp;Abdelnasser Abidli,&nbsp;Lucie Schiavo,&nbsp;Loïc Jeanmart,&nbsp;Gilles Hanquet,&nbsp;William D. Lubell","doi":"10.1002/ejoc.202580801","DOIUrl":"https://doi.org/10.1002/ejoc.202580801","url":null,"abstract":"<p><b>The Front Cover</b> illustrates the numerous and major strategies developed for the sustainable total synthesis of natural products, while shedding light on the use of readily available chiral pools, such as (−)-sclareol, as a key synthesis approach. (−)-Sclareol has effectively enabled the synthesis of numerous complex natural products through diverse key intermediates and building blocks. Thus, (−)-sclareol has created shortcuts to access valuable bioactive molecules via greener and cost-effective routes. More information can be found in the Review by A. Selka, A. Abidli, G. Hanquet and co-workers (DOI: 10.1002/ejoc.202400983). Cover designed by A. Abidli.\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 8","pages":""},"PeriodicalIF":2.5,"publicationDate":"2025-02-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ejoc.202580801","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143475631","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}
引用次数: 0
Brønsted‐Acid Catalyzed Aldehyde Insertion to Construct C−X Bond: High Regio‐ and Chemoselectivity Synthesis of Dihydrobenzo[1,5]oxazocines and Pyrrolo[3,4‐ d]tetrahydropyrimidines Brønsted-Acid催化醛插入构建C-X键：高区域选择性和化学选择性合成二氢苯并[1,5]恶唑嘧啶和吡咯[3,4-d]四氢嘧啶
IF 2.5 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-02-24 DOI: 10.1002/ejoc.202401287
Yuan‐Min Wen , Teng Liu , Gui‐Yun Zeng , Jun‐Jie Li , Zeng‐Hong Yao , Chi‐Xian He , Chao Huang
{"title":"Brønsted‐Acid Catalyzed Aldehyde Insertion to Construct C−X Bond: High Regio‐ and Chemoselectivity Synthesis of Dihydrobenzo[1,5]oxazocines and Pyrrolo[3,4‐ d]tetrahydropyrimidines","authors":"Yuan‐Min Wen ,&nbsp;Teng Liu ,&nbsp;Gui‐Yun Zeng ,&nbsp;Jun‐Jie Li ,&nbsp;Zeng‐Hong Yao ,&nbsp;Chi‐Xian He ,&nbsp;Chao Huang","doi":"10.1002/ejoc.202401287","DOIUrl":"10.1002/ejoc.202401287","url":null,"abstract":"<div><div>Aldehydes as one of the most widely building blocks, have been frequently utilized as privileged C1 electrophile units and exhibited versatile applications to construct carbon‐heteroatom and carbon‐carbon bond. We herein described a novel Brønsted‐acid catalyzed aldehydes insertion reaction with maleimide‐based 1, n‐C, O/N‐synthons, involving a high regio‐ and chemoselectivity [6/7 + 1]or [3 + 1 + 1 + 1]manner. The maleimide‐based 1, n‐C, O/N‐synthons (n = 3, 6, 7) were originally designed and developed by our group which were used as flexible bisnucleophiles. By this tandem annulations approach, two types of structurally diverse medium‐sized heterocycles were synthesized in good to excellent yields (74–91 %) and with excellent selectivity, including dihydrobenzo[1,5]oxazocines (24 examples) and pyrrolo[3,4‐ <em>d</em>]tetrahydropyrimidines (22 examples). Significantly, formaldehyde, long‐chain aliphatic aldehydes and aromatic aldehydes can act as C1 electrophile units catalyzed by racemic BINOL‐derived phosphoric acid catalyst in these transformations, which then selectively attacked the OH or NH group bearing in functionalized maleimides and underwent the formation of C−C, C−O or C−N bond in a short time under microwave irradiation conditions.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 8","pages":"Article e202401287"},"PeriodicalIF":2.5,"publicationDate":"2025-02-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142880137","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}
引用次数: 0
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