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PIFA-Mediated C─H Thiolation and Selenylation of Pseudo-Anomeric Position of Glycals with Disulfides or Diselenides at Room Temperature 室温下pifa介导的糖醛与二硫化物或二硫化物的C─H硫代和硒化反应
IF 2.7 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-07-13 DOI: 10.1002/ajoc.202500291
Neha Singh Chauhan, Dr. Pintu Kumar Mandal
{"title":"PIFA-Mediated C─H Thiolation and Selenylation of Pseudo-Anomeric Position of Glycals with Disulfides or Diselenides at Room Temperature","authors":"Neha Singh Chauhan,&nbsp;Dr. Pintu Kumar Mandal","doi":"10.1002/ajoc.202500291","DOIUrl":"10.1002/ajoc.202500291","url":null,"abstract":"<p>Herein, we report the [Bis(trifluoroacetoxy)iodo]benzene mediated C(sp<sup>2</sup>)−H bond thiolation and selenylation of <i>pseudo</i>-anomeric position of C2-branched glycals using sugar, aliphatic, and aromatic disulfides or diselenides partner at room temperature. This developed protocol offers a metal-free synthetic route that potentiates the generation of a library of 1-thiotrehaloses and thio/selenoglycosides bearing a variety of functional groups in moderate to good yields. Concerning the glycal partners, the peracetylated protected analogue showed a similar reactivity like the benzylated model substrates under this conditions. Based on control experiments, a plausible radical pathway mechanism is proposed.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 9","pages":""},"PeriodicalIF":2.7,"publicationDate":"2025-07-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145058100","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Divergent Radical, Dimerization, and Carbene Formation from One-Electron Reduction of 2-Cyanoimidazolium Salts 2-氰咪唑盐单电子还原的发散自由基、二聚化和卡宾形成
IF 2.7 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-07-13 DOI: 10.1002/ajoc.202500443
Jawon Jang, Jaelim Kim, Prof. Eunsung Lee
{"title":"Divergent Radical, Dimerization, and Carbene Formation from One-Electron Reduction of 2-Cyanoimidazolium Salts","authors":"Jawon Jang,&nbsp;Jaelim Kim,&nbsp;Prof. Eunsung Lee","doi":"10.1002/ajoc.202500443","DOIUrl":"10.1002/ajoc.202500443","url":null,"abstract":"<p>Nitriles are indispensable synthetic building blocks for the construction of nitrogen-containing molecules with broad applications in pharmaceuticals, agrochemicals, and materials science. While their conventional two-electron reductions enable transformations into amines, carboxylic acids, and aldehydes, their one-electron reduction pathways, which lead to radical formation, remain largely unexplored. In this study, we report the rational synthesis of 2-cyanoimidazolium salts and investigate their one-electron reduction pathways. Upon reduction, these compounds yield both organic radicals and free carbenes. Notably, the free carbene formation occurs via electrophilic cyanide transfer proceeding through a mesoionic carbene (MIC) intermediate. We further demonstrate that the steric bulkiness of imidazolium N-substituents plays a critical role in determining radical stability. The imidazolium with a sterically bulky substituent generates the persistent radical, which is characterized by electron paramagnetic resonance (EPR) spectroscopy. In contrast, heating the radical with a less bulky N-substituent leads to dimerization, forming new C(sp)─C(sp<sup>2</sup>) and C(sp<sup>2</sup>)─N bonds. Insights into their mechanism are supported by density functional theory (DFT) calculations.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 9","pages":""},"PeriodicalIF":2.7,"publicationDate":"2025-07-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145058099","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
The Synthesis of Cyclopropyl-Fused Tetrahydrofurans from Vinylcyclopropanes 乙烯基环丙烷合成环丙基熔合四氢呋喃
IF 2.7 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-07-12 DOI: 10.1002/ajoc.70110
Alexander J. Craig, Andrew P. Cording, Selena C. L. Gilmer, Jackson S. Henneveld, Sinan Gai, Owain H. Harker, Nigel T. Lucas, Bill C. Hawkins
{"title":"The Synthesis of Cyclopropyl-Fused Tetrahydrofurans from Vinylcyclopropanes","authors":"Alexander J. Craig,&nbsp;Andrew P. Cording,&nbsp;Selena C. L. Gilmer,&nbsp;Jackson S. Henneveld,&nbsp;Sinan Gai,&nbsp;Owain H. Harker,&nbsp;Nigel T. Lucas,&nbsp;Bill C. Hawkins","doi":"10.1002/ajoc.70110","DOIUrl":"10.1002/ajoc.70110","url":null,"abstract":"<p>The rapid synthesis of oxabicyclo[3.1.0]hexanols from various vinylcyclopropanes is described. Several carbonyl functionalities were incorporated, as were a range of electronically and sterically diverse aromatic and aliphatic substituents. This structurally unusual building block was then showcased through the rapid synthesis of a series of structurally complex polycyclic compounds.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 9","pages":""},"PeriodicalIF":2.7,"publicationDate":"2025-07-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://aces.onlinelibrary.wiley.com/doi/epdf/10.1002/ajoc.70110","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145057986","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Visible-Light-Driven Synthesis of Ester-Substituted Imidazole-Fused Heterocycles via Tandem Radical Cyclization 串联自由基环化在可见光下合成酯取代咪唑-融合杂环
IF 2.7 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-07-11 DOI: 10.1002/ajoc.202500479
Qian Yan, Mai Zhang, Jie Yao, Zi-Han Zhuang, Shi-Hua Chen, Shi-Hai Yang, Zhi-Wei Li, Jiang-Sheng Li
{"title":"Visible-Light-Driven Synthesis of Ester-Substituted Imidazole-Fused Heterocycles via Tandem Radical Cyclization","authors":"Qian Yan,&nbsp;Mai Zhang,&nbsp;Jie Yao,&nbsp;Zi-Han Zhuang,&nbsp;Shi-Hua Chen,&nbsp;Shi-Hai Yang,&nbsp;Zhi-Wei Li,&nbsp;Jiang-Sheng Li","doi":"10.1002/ajoc.202500479","DOIUrl":"10.1002/ajoc.202500479","url":null,"abstract":"<p>A novel tandem radical cyclization strategy is reported for the efficient synthesis of ester-functionalized imidazole-fused heterocycles. This method leverages visible-light photocatalysis and modular substrate design to achieve high regioselectivity and atom economy. The protocol demonstrates broad compatibility with diverse <i>N</i>-allylimidazoles and bromoacetates, enabling rapid construction of structurally complex products under mild conditions.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 9","pages":""},"PeriodicalIF":2.7,"publicationDate":"2025-07-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145057981","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
K2S2O8-Promoted Direct Chalcogenation and Nitrosation at C-3 Position of Imidazo[1,2-a]pyridines Under Mild Conditions 温和条件下k2s2o8促进咪唑[1,2-a]吡啶C-3位直接加氢和亚硝化反应
IF 2.7 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-07-11 DOI: 10.1002/ajoc.202500508
Surya Kanta Samanta, Rumpa Sarkar, Biman Bera, Mrinal K. Bera
{"title":"K2S2O8-Promoted Direct Chalcogenation and Nitrosation at C-3 Position of Imidazo[1,2-a]pyridines Under Mild Conditions","authors":"Surya Kanta Samanta,&nbsp;Rumpa Sarkar,&nbsp;Biman Bera,&nbsp;Mrinal K. Bera","doi":"10.1002/ajoc.202500508","DOIUrl":"10.1002/ajoc.202500508","url":null,"abstract":"<p>K<sub>2</sub>S<sub>2</sub>O<sub>8</sub>-promoted an efficient method for regioselective chalcogenation (S and Se), and nitrosation of imidazo[1,2-<i>a</i>]pyridines at C-3 position was achieved using diorganoyl dichalcogenides, thiols, and sodium nitrite under metal-free conditions. This approach provides direct access to structurally diverse chalcogenated and nitroso imidazopyridines through sp<sup>2</sup> C─H functionalization in good to excellent yield by using K<sub>2</sub>S<sub>2</sub>O<sub>8</sub> as an oxidant. The operational simplicity, good regioselectivity, high atom economy, and use of ambient conditions are the attractive features of the reaction.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 9","pages":""},"PeriodicalIF":2.7,"publicationDate":"2025-07-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145057979","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Advances in the Synthesis and Reactivity of Selenadiazoles 硒二唑类化合物的合成及其反应性研究进展
IF 2.7 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-07-11 DOI: 10.1002/ajoc.202500577
Abdul Qaiyum Ramle, Edward R.T. Tiekink
{"title":"Advances in the Synthesis and Reactivity of Selenadiazoles","authors":"Abdul Qaiyum Ramle,&nbsp;Edward R.T. Tiekink","doi":"10.1002/ajoc.202500577","DOIUrl":"10.1002/ajoc.202500577","url":null,"abstract":"<p>The four isomeric selenadiazoles comprise five-membered SeN<sub>2</sub>C<sub>2</sub> heterocyclic rings and represent a prominent class of organoselenium scaffolds that have received considerable attention in recent years owing to their notable applications in medicinal and materials chemistry. To explore their functionalities, several synthetic methodologies have been developed to diversify these scaffolds with a range of substituents. Cyclization reactions remain the most prevalent approach by employing substituted hydrazines, selonamides, cyano nitriles, and amines under versatile reaction conditions and reagents. This review presents an overview of the strategies reported over the past decade for accessing the four isomeric forms of selenadiazole. The synthetic scope, functionalization and reactivity of the reactions are discussed. Additionally, the non-covalent chalcogen- and halogen-bonding interactions of selected derivatives are reviewed, when present.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 9","pages":""},"PeriodicalIF":2.7,"publicationDate":"2025-07-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145057980","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Synthetic Approaches to Chalcone Synthesis 查尔酮的合成方法
IF 2.7 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-07-11 DOI: 10.1002/ajoc.202500099
Fatemeh Doraghi, Yasin Mohammadkhani Kalooei, Mehran Ghasemi, Bagher Larijani, Mohammad Mahdavi, Ahmed Al-Harrasi
{"title":"Synthetic Approaches to Chalcone Synthesis","authors":"Fatemeh Doraghi,&nbsp;Yasin Mohammadkhani Kalooei,&nbsp;Mehran Ghasemi,&nbsp;Bagher Larijani,&nbsp;Mohammad Mahdavi,&nbsp;Ahmed Al-Harrasi","doi":"10.1002/ajoc.202500099","DOIUrl":"10.1002/ajoc.202500099","url":null,"abstract":"<p>Chalcones are widely found in natural products, pharmaceuticals, food, and cosmetic industries. They have been used as key intermediates in the development of various biologically active compounds. Given their high importance, the chemistry of chalcones has always been the most demanded and focused area of research in the scientific community. A wide variety of transition metals, including palladium, gold, silver, rhodium, zinc, copper, iron, nickel, and manganese, can efficiently catalyze the synthesis of chalcones. The preparation of chalcones can also be achieved through metal-free systems using base, acid, and oxidant as promoters or under catalyst-free conditions. This review describes the synthesis of chalcone derivatives under metal catalysis or metal-free systems.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 8","pages":""},"PeriodicalIF":2.7,"publicationDate":"2025-07-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144832537","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Direct C(sp3)─H Thiolation with Disulfides via Light Photoredox Catalysis 光氧化还原催化直接C（sp3）─H硫基化与二硫化物
IF 2.7 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-07-11 DOI: 10.1002/ajoc.202500252
Junsong Song, Mengqin Tao, Honghua Jia, Jiang-Kai Qiu, Jian Wang, Canliang Ma, Kai Guo
{"title":"Direct C(sp3)─H Thiolation with Disulfides via Light Photoredox Catalysis","authors":"Junsong Song,&nbsp;Mengqin Tao,&nbsp;Honghua Jia,&nbsp;Jiang-Kai Qiu,&nbsp;Jian Wang,&nbsp;Canliang Ma,&nbsp;Kai Guo","doi":"10.1002/ajoc.202500252","DOIUrl":"10.1002/ajoc.202500252","url":null,"abstract":"<p>Organosulfur compounds hold significant application value in fields such as medicine and materials science. However, due to the poisoning effect of sulfur on metal catalysts, the development of methods for constructing C-S bonds has notably lagged behind strategies for synthesizing other carbon-heteroatom bonds. This study reports a photoinduced C-H direct functionalization strategy that enables the construction of C-S bonds with disulfides under mild conditions. The reaction system exhibits excellent substrate compatibility, with a variety of ethers, allylic compounds, amides containing C(sp<sup>3</sup>)-H bonds, as well as alkyl and aryl disulfides participating efficiently in the reaction. This synthetic method offers significant advantages: broad substrate scope, mild reaction conditions, and high atom economy, providing an efficient and convenient new approach for the synthesis of thioether compounds.\u0000</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 9","pages":""},"PeriodicalIF":2.7,"publicationDate":"2025-07-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145057978","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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 Two Stereoisomers of a Natural Cyclotetrapeptide and Four Stereoisomeric Diheteropeptins Through Late-Stage Scaffold Diversification 一种天然环四肽的两种立体异构体和四种二异肽的后期支架分化合成
IF 2.7 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-07-11 DOI: 10.1002/ajoc.202500232
Rajat Ghosh, Manisha Kundu, Prof. Dr. Shital K. Chattopadhyay
{"title":"Synthesis of Two Stereoisomers of a Natural Cyclotetrapeptide and Four Stereoisomeric Diheteropeptins Through Late-Stage Scaffold Diversification","authors":"Rajat Ghosh,&nbsp;Manisha Kundu,&nbsp;Prof. Dr. Shital K. Chattopadhyay","doi":"10.1002/ajoc.202500232","DOIUrl":"10.1002/ajoc.202500232","url":null,"abstract":"<p>A concise synthetic route has been developed to access two stereoisomers 5a-b of a biologically enticing naturally occurring cyclic tetrapeptide through late-stage diversification of the cyclopeptidic scaffold 8. A cross-metathesis reaction of this template with the olefins 9a-b, preparaed from enantiomeric methyl lactates 10, produced the α,β-unsaturated ketones 7a-b which on subsequent hydrogenation produced the desired targets 5a-b in good overall yields.These two stereo-isomers, 5a-b, were then used for the preparation of four stereoisomers of the closely related and biologically relevant cyclic tetrapeptide diheteropeptin 1. A syn-selective reduction of the hydroxyketones 5a-b with lithium tri-tert-butoxyaluminium hydride produced the syn-isomers 1a and 1c, whereas an anti-selective reduction with lithium triethylborohydride produced the pseudo-enantiomeric targets 1b and 1d with similar yield and selectivity. Thus, an ensemble of six cyclic tetrapeptides with stereochemical diversity was generated from the common template 8 in two-three steps.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 9","pages":""},"PeriodicalIF":2.7,"publicationDate":"2025-07-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145057982","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Molecular Iodine-Catalyzed 1,6-Conjugated Addition of Enaminones on para-Quinone Methides 分子碘催化1,6-共轭对醌类化合物上胺酮的加成
IF 2.7 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-07-10 DOI: 10.1002/ajoc.202500501
Megha Rawat, Rajnish Budhwan, Pooja Dahiya, Anoop Yadav, Prof. Dr. Rama Krishna Peddinti
{"title":"Molecular Iodine-Catalyzed 1,6-Conjugated Addition of Enaminones on para-Quinone Methides","authors":"Megha Rawat,&nbsp;Rajnish Budhwan,&nbsp;Pooja Dahiya,&nbsp;Anoop Yadav,&nbsp;Prof. Dr. Rama Krishna Peddinti","doi":"10.1002/ajoc.202500501","DOIUrl":"10.1002/ajoc.202500501","url":null,"abstract":"<p>A highly efficient and metal-free protocol has been developed for the synthesis of a series of enaminone derivatives functionalized with unsymmetrical diarylmethyl units via 1,6-conjugate addition of enaminones viz. arylaminocyclohexenones and <i>N</i>-alkyl arylaminomaleimides, using molecular iodine (I₂) under mild conditions. This reaction proceeds at ambient temperature, yielding structurally diverse products with excellent functional group tolerance. The optimized conditions demonstrated remarkable substrate scope, including electron-donating and electron-withdrawing substituents on both <i>para</i>-quinone methides (<i>p</i>-QMs) and enaminones. The use of I₂ as a catalyst offers an environmentally benign and cost-effective alternative to transition metals, ensuring operational simplicity. The scalability of the method was successfully demonstrated through gram-scale synthesis.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 9","pages":""},"PeriodicalIF":2.7,"publicationDate":"2025-07-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145057880","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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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