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Recent Advances in Diphenylmethanone Oxime Reagent Chemistry for Unsaturated Bond Bifunctionalization via Energy Transfer Catalysis
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2024-12-10 DOI: 10.1002/ejoc.202401186
Xue-Ling Luo, Di-Jing Luo, Lu-Lu Qin, Zhi-Peng Ye, Peng-Ju Xia
{"title":"Recent Advances in Diphenylmethanone Oxime Reagent Chemistry for Unsaturated Bond Bifunctionalization via Energy Transfer Catalysis","authors":"Xue-Ling Luo, Di-Jing Luo, Lu-Lu Qin, Zhi-Peng Ye, Peng-Ju Xia","doi":"10.1002/ejoc.202401186","DOIUrl":"https://doi.org/10.1002/ejoc.202401186","url":null,"abstract":"The concurrent installation of C-X (C, O, S, N) and C-N bonds across unsaturated bond skeletons is an effective strategy for the preparation of ubiquitous motifs in pharmaceuticals and bioactive compounds. In recent years, the rapid development of bifunctionalization reactions has resulted in the emergence of bifunctional reagents as a research hotspot in this field. Among these, diphenylmethanone oxime reagents with highly active N-O bonds featuring low dissociation energy have significantly advanced the research of bifunctionalization. These reagents possess special features to simultaneously form two chemical bonds or introduce two functional groups, which not only streamlines synthetic pathways but also enhances synthetic efficiency, displaying an excellent atom- and step-economy. In addition, diphenylmethanone oxime reagents have been extensively employed in organic synthesis, attributed to their ability to facilitate the construction of complex organic structures and to provide innovative reaction pathways. In this review, we present a comprehensive overview of various diphenylmethanone oxime reagents and their applications in the bifunctional modification of unsaturated bonds through visible-light-mediated triplet–triplet energy transfer catalysis (TTEnT).","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"21 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-12-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142805053","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
Photochemical-, Electrochemical-, and Photoelectrochemical- Catalyzed Hydrogen Atom Transfer from Aldehydes to Acyl Radicals and Their Transformations
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2024-12-10 DOI: 10.1002/ejoc.202401206
Lei Wang, Fang Wang, Bin Wang, Qidi Wang
{"title":"Photochemical-, Electrochemical-, and Photoelectrochemical- Catalyzed Hydrogen Atom Transfer from Aldehydes to Acyl Radicals and Their Transformations","authors":"Lei Wang, Fang Wang, Bin Wang, Qidi Wang","doi":"10.1002/ejoc.202401206","DOIUrl":"https://doi.org/10.1002/ejoc.202401206","url":null,"abstract":"Acyl radical has assumed an eminent position in the synthetic chemistry due to its unique and often highly reactive nature. Using aldehyde as acyl radical source does not require the prefunctionalization of substrate. Furthermore, the formation of acyl radical can be achieved through a hydrogen atom transfer (HAT) process. In recent years, photochemical-, electrochemical-, and photoelectrochemical-catalyzed intermolecular HAT from aldehydes have been regarded as mild and sustainable routes for the generation of acyl radicals. Herein, we discuss some of the key advancements in the past 6 years in photo-, electro-, and photoelectro-catalyzed generation of acyl radicals from aldehydes and their utilization. We also highlight the mechanistic insights that have emerged from these transformations.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"10 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-12-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142805049","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
β-halovinyl Aldehydes: Multifaceted Versatile Building Blocks in Organic Synthesis
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2024-12-09 DOI: 10.1002/ejoc.202401058
Virender Singh, Paras Saini, Jyoti -, Pawan Kumar Sharma
{"title":"β-halovinyl Aldehydes: Multifaceted Versatile Building Blocks in Organic Synthesis","authors":"Virender Singh, Paras Saini, Jyoti -, Pawan Kumar Sharma","doi":"10.1002/ejoc.202401058","DOIUrl":"https://doi.org/10.1002/ejoc.202401058","url":null,"abstract":"β-halovinyl aldehydes serve as a valuable building blocks in organic synthesis. These aldo-x bifunctional building blocks (AXB3s) contain a alkenic double bond (vinyl) as well as a formyl group along with a halogen atom (Cl, Br, I) bonded with the β-carbon atom of vinyl aldehyde. Owing to the presence of these multiple reactive sites, β-halovinyl aldehydes act as a suitable precursor for Michael addition, direct addition, cross-coupling reactions, condensation reactions, nucleophilic substitution reactions, domino reactions, MCRs, Diels-Alder reaction, functional group transformation reactions and enantioslective transformations. Therefore, a comprehensive review on synthetic exploration of β-halovinyl aldehydes has been carried out for the generation of reactive intermediates and diverse bioactives heterocycles by using various C-C, C-N, C-S and C-O bond forming reactions. In this review, we have assembled the literature from mid-2007 to Jan 2024.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"21 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-12-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142797818","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
Strong Acid‐free Homogeneous Catalytic Systems for the Ester Products Synthesis by Alkenes Alkoxycarbonylation: Recent Advances
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2024-12-09 DOI: 10.1002/ejoc.202401010
Nadezhda Tengizovna Sevostyanova, Sergey Alexandrovich Batashev
{"title":"Strong Acid‐free Homogeneous Catalytic Systems for the Ester Products Synthesis by Alkenes Alkoxycarbonylation: Recent Advances","authors":"Nadezhda Tengizovna Sevostyanova, Sergey Alexandrovich Batashev","doi":"10.1002/ejoc.202401010","DOIUrl":"https://doi.org/10.1002/ejoc.202401010","url":null,"abstract":"Alkoxycarbonylation represents a method for the ester products synthesis from available reagents – unsaturated compounds, alcohols, and CO. The beginning of research on this reaction was laid in W. Reppe’ works in 1953. In early works, halides and carbonyls of Co, Ni, Rh, and Ir were used as catalysts, and alkoxycarbonylation was often complicated by the unsaturated compounds hydroformylation or alcohol carbonylation. In recent decades, in the presence of the most active and selective Pd‐phosphine systems with strong protonic acids, the products are typically only isomeric esters, which corresponds to the creating waste‐free production principles. At present, a large‐capacity synthesis process for methyl methacrylate, dubbed Alpha, is in operation, with the initial stage being ethylene methoxycarbonylation. In light of these developments, there is a growing interest among chemists and technologists in alkenes alkoxycarbonylation. The use of strong protonic acids as co‐catalysts is essential for the formation of active catalytic complexes. However, these acids are highly corrosive and can cause the alkenes isomerisation. This review is devoted to the analysis of acid‐free homogeneous Pd‐, Ru‐, Co‐, and Ni‐catalysts employed in alkenes alkoxycarbonylation over the past 15 years. As a result, polymers, monomers and other valuable linear and branched esters were obtained.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"15 1 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-12-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142797572","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
A green synthetic approach to construct C2‐quaternary indolin‐3‐ones at room temperature via regioselective oxidative dearomatization of indoles
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2024-12-07 DOI: 10.1002/ejoc.202401037
Pinaki Bhattacharjee, Sudip Dey, Shalini Kar, Mohammed Rafi, SUNNAPU PRASAD, Parasuraman Jaisankar
{"title":"A green synthetic approach to construct C2‐quaternary indolin‐3‐ones at room temperature via regioselective oxidative dearomatization of indoles","authors":"Pinaki Bhattacharjee, Sudip Dey, Shalini Kar, Mohammed Rafi, SUNNAPU PRASAD, Parasuraman Jaisankar","doi":"10.1002/ejoc.202401037","DOIUrl":"https://doi.org/10.1002/ejoc.202401037","url":null,"abstract":"A new synthetic strategy for the construction of C2‐quaternary indole for the formation of Indolin‐3‐ones has been explored via indium(III) trifluoromethansulphonate catalyst at room temperature with TBHP as a green oxidant in water. This approach for the oxidative dearomatization process allows to produce natural product Halichrome A and a broad range of C2‐arylated Indolin‐3‐ones under a milder condition in very good yields. The oxidative self‐dimerization and self‐trimerization of various indole derivatives have also been achieved under the same conditions.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"13 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-12-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142788395","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 the Hydroxylation of Boronic Acids
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2024-12-06 DOI: 10.1002/ejoc.202401152
Yameng Wan, Xiang Li, Junying Ma, Guisheng Zhang
{"title":"Recent Advances in the Hydroxylation of Boronic Acids","authors":"Yameng Wan, Xiang Li, Junying Ma, Guisheng Zhang","doi":"10.1002/ejoc.202401152","DOIUrl":"https://doi.org/10.1002/ejoc.202401152","url":null,"abstract":"Hydroxylated compounds represent a significant and diverse class of substances in the field of chemistry. These compounds play critical roles in various chemical reactions and are essential components in numerous industrial applications. Recent years have witnessed remarkable advancements in the synthesis of hydroxylated compounds, especially those derived from boronic acids. The synthesis of hydroxylated compounds from boronic acids typically involves the utilization of various types of catalysts, which are essential for enhancing reaction rates and selectivity, including metal catalysts such as CuFe₂O₄, Cu@C₃N₄, AgNPs, and Ti0.97Ni0.3O1.97, as well as non-metal catalysts like polycaprolactone (PCL), TFB-BMTH COF materials, C70, and graphene oxide (GO). These catalytic reactions often require the addition of oxidants such as hydrogen peroxide (H₂O₂) or molecular oxygen, which serve as critical reagents in the hydroxylation process. In certain cases, organic bases act as electron donors to propel the reaction. Furthermore, some studies have reported oxidative hydroxylation reactions that are catalyst-free.This review aims to summarize the recent advancements and breakthroughs in the synthesis of hydroxylated compounds from boronic acids, with a particular focus on research conducted from 2014 to 2024.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"37 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-12-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142783016","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
Visible‐Light‐Induced Mpg‐C3N4 Catalyzed C(sp2)‐H Thiocyanation of Ketene Dithioacetals
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2024-12-06 DOI: 10.1002/ejoc.202401180
Fumeng Yin, Shan Hu, Shuwei Zhu, Shifeng Xing, Hongjun Zhu
{"title":"Visible‐Light‐Induced Mpg‐C3N4 Catalyzed C(sp2)‐H Thiocyanation of Ketene Dithioacetals","authors":"Fumeng Yin, Shan Hu, Shuwei Zhu, Shifeng Xing, Hongjun Zhu","doi":"10.1002/ejoc.202401180","DOIUrl":"https://doi.org/10.1002/ejoc.202401180","url":null,"abstract":"Using mesoporous graphite carbon nitride (mpg‐C3N4) as metal‐free heterogeneous catalyst, the thiocyanation of ketene dithioacetals was achieved under visible light irradiation with oxygen as green oxidant and without any other additives. The present protocol has excellent functional group tolerance and the desired tetrasubstituted alkenyl thiocyanides were obtained in moderate to good yields. Moreover, the recyclable mpg‐C3N4 catalyst could be used at least 6 times without significant loss of activities. A series of mechanistic validation experiments indicated that the reaction involves a radical process.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"138 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-12-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142783017","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
Base promoted chemoselective reduction of α‐keto amides and α‐keto esters with TsNHNH2
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2024-12-06 DOI: 10.1002/ejoc.202401199
Yifei Wu, Kewei Liu, Feiyue Hao, Erqiang Zhao, Zhengneng Jin, Jiashou Wu
{"title":"Base promoted chemoselective reduction of α‐keto amides and α‐keto esters with TsNHNH2","authors":"Yifei Wu, Kewei Liu, Feiyue Hao, Erqiang Zhao, Zhengneng Jin, Jiashou Wu","doi":"10.1002/ejoc.202401199","DOIUrl":"https://doi.org/10.1002/ejoc.202401199","url":null,"abstract":"A method for chemoselective reduction of α‐keto amides and α‐keto esters using tosylhydrazine in the presence of NaHCO3 has been developed. A variety of α‐hydroxy amides and α‐hydroxy esters were obtained in good to excellent yields, demonstrating the efficiency of the present protocol. A possible reaction mechanism is proposed based on the deuterium‐labelling experiments.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"8 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-12-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142783067","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
Three-Component Alkylsulfonylation of 1-Acryloyl-2-cyanoindoles with Hantzsch Esters through Sulfur Dioxide Insertion
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2024-12-04 DOI: 10.1002/ejoc.202401211
Long-Jin Zhong, Xuan Shang, Hui Chen, Rui-Xin Liu, Kewen Tang, Quan Zhou, Yu Liu
{"title":"Three-Component Alkylsulfonylation of 1-Acryloyl-2-cyanoindoles with Hantzsch Esters through Sulfur Dioxide Insertion","authors":"Long-Jin Zhong, Xuan Shang, Hui Chen, Rui-Xin Liu, Kewen Tang, Quan Zhou, Yu Liu","doi":"10.1002/ejoc.202401211","DOIUrl":"https://doi.org/10.1002/ejoc.202401211","url":null,"abstract":"A three-component alkylsulfonylation/cyclization/ hydrolysis relay reaction of 1-acryloyl-2-cyanoindoles with 4-alkyl Hantzsch esters and Na2S2O5 to access a series of alkylsulfonyl pyrrolo[1,2-a]indolediones derivatives involving in situ sulfur dioxide insertion is established. With this method, a variety of primary and secondary alkyl radicals can be used for trapping sulfur dioxide and in situ formed corresponding alkylsulfonyl radical intermediates, followed by alkyl sulfonyl radical addition, cyclization and hydrolysis. In addition, this reaction goes through once selective cleavage of σ carbon-carbon bond and following successively formation of three new chemical bonds, in which cyano group acts as the dual roles, including the radical acceptor and carbonyl source.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"17 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-12-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142763729","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
Benzoisoxazoles as Privileged Scaffolds in Design and Synthesis of N-Containing Molecules: Recent Update
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2024-12-04 DOI: 10.1002/ejoc.202401021
Xingyu Chen, Wenbo Ma, Tairan Kang, Peng Sun, Xiaoqiang Guo
{"title":"Benzoisoxazoles as Privileged Scaffolds in Design and Synthesis of N-Containing Molecules: Recent Update","authors":"Xingyu Chen, Wenbo Ma, Tairan Kang, Peng Sun, Xiaoqiang Guo","doi":"10.1002/ejoc.202401021","DOIUrl":"https://doi.org/10.1002/ejoc.202401021","url":null,"abstract":"Benzoisoxazoles, with a distinctive 10-π-electron system and significant polarity, readily trigger N-O bond cleavage, enabling multifaceted applications in organic synthesis. Over the past decade, the exponentially increased use of benzoisoxazoles towards the synthesis of highly valuable N-containing scaffolds, especially N-heterocycles, has garnered substantial attention. In this review, we summarize recent developments in the transformation of 2,1- and 1,2-benzoisoxazoles since 2015, highlighting the neglected resemblances of these two nitroxy heterocycles. Key processes in the assorted reactions of benzoisoxazoles, including mechanisms, scope, catalyst-controlled chemodivergence, current limitations, and developmental prospects, are also introduced and discussed.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"19 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-12-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142763726","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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