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Asian Journal of Organic Chemistry最新文献

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Defluorinative Hydroxylation Promoted by Silica to Access Optically Pure Hexahydrofuranocarbazole via [4+2] Addition Reaction 二氧化硅催化脱氟羟基化通过[4+2]加成反应获得光学纯的六氢呋喃咔唑
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-03-01 DOI: 10.1002/ajoc.202400752
Madavi S. Prasad , Thoudam Bedanta , Souvik Saha , Aman Kumar Jha , Sankar Bharani , Ponnada Chandrasekhar
{"title":"Defluorinative Hydroxylation Promoted by Silica to Access Optically Pure Hexahydrofuranocarbazole via [4+2] Addition Reaction","authors":"Madavi S. Prasad ,&nbsp;Thoudam Bedanta ,&nbsp;Souvik Saha ,&nbsp;Aman Kumar Jha ,&nbsp;Sankar Bharani ,&nbsp;Ponnada Chandrasekhar","doi":"10.1002/ajoc.202400752","DOIUrl":"10.1002/ajoc.202400752","url":null,"abstract":"<div><div>Crafting an efficient strategy for the synthesis of biologically active and functionally rich hexahydrofuranocarbazole is a highly desirable but demanding pursuit. This research elucidates a groundbreaking strategy involving an unanticipated defluorinative hydroxylation reaction facilitated by silica gel, yielding highly enantio‐ and diastereoselective hexahydrofuranocarbazole frameworks. This method results in the formation of five consecutive chiral centers, including three quaternary stereocenters and an all‐carbon spiro center, <em>via</em> an aminocatalytic asymmetric remote [4+2] addition process. The developed methodology allows for the construction of a diverse array of products (24 examples, up to &gt;99 % <em>ee</em> and 17 : 1 <em>dr</em>), reflecting its notable substrate scope. Furthermore, we demonstrate the feasibility of gram‐scale synthesis and control experiments that underscore the methodological advancements and provide insights into the underlying mechanism.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 3","pages":"Article e202400752"},"PeriodicalIF":2.8,"publicationDate":"2025-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143622391","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
Solvent Effects in the Reactions of Alkenes with gem‐Bis(triflyl)ethylene 烯烃与双（三氟基）乙烯反应中的溶剂效应
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-03-01 DOI: 10.1002/ajoc.202400651
Dr. Hikaru Yanai , Reon Sano , Dr. Shoki Hoshikawa , Prof. Dr. Takashi Matsumoto
{"title":"Solvent Effects in the Reactions of Alkenes with gem‐Bis(triflyl)ethylene","authors":"Dr. Hikaru Yanai ,&nbsp;Reon Sano ,&nbsp;Dr. Shoki Hoshikawa ,&nbsp;Prof. Dr. Takashi Matsumoto","doi":"10.1002/ajoc.202400651","DOIUrl":"10.1002/ajoc.202400651","url":null,"abstract":"<div><div>The reaction modes in the reactions of several alkenes with Tf<sub>2</sub>C=CH<sub>2</sub> (Tf=CF<sub>3</sub>SO<sub>2</sub>) have been controlled by the reaction solvents. For example, although the reaction with allylsilanes selectively produced normal allylation products in MeCN, <em>gem</em>‐bis(triflyl)cyclopentanes were formed in toluene. In particular, a selective formation of the (3+2) cycloadducts was achieved by using sterically hindered allylsilanes. We also found notable solvent effects in the reaction with simple alkenic hydrocarbons. That is, in hot toluene, the Alder ene reaction of the alkenes with Tf<sub>2</sub>C=CH<sub>2</sub> smoothly proceeded to give the corresponding (<em>E</em>)‐alkenes bearing a superacidic bis(triflyl)methyl group.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 3","pages":"Article e202400651"},"PeriodicalIF":2.8,"publicationDate":"2025-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ajoc.202400651","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143622436","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
Origin of Regioselectivity Switch in Pyridinium Functionalizations with Phosphinoyl and Carbamoyl Radicals 磷酰基和氨基甲酰基基吡啶功能化中区域选择性开关的起源
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-03-01 DOI: 10.1002/ajoc.202400701
Dr. Lingfei Hu , Wenyao Ding , Wei Liu , Limeng Wang , Dr. Xiangying Lv , Prof. Gang Lu
{"title":"Origin of Regioselectivity Switch in Pyridinium Functionalizations with Phosphinoyl and Carbamoyl Radicals","authors":"Dr. Lingfei Hu ,&nbsp;Wenyao Ding ,&nbsp;Wei Liu ,&nbsp;Limeng Wang ,&nbsp;Dr. Xiangying Lv ,&nbsp;Prof. Gang Lu","doi":"10.1002/ajoc.202400701","DOIUrl":"10.1002/ajoc.202400701","url":null,"abstract":"<div><div>The origins of regioselectivity switch in pyridinium phosphinoylation and carbamoylation were computationally investigated using energy decomposition analysis. The results reveal that the preference for regioselectivity arises from distinct intermolecular interactions between phosphinoyl/carbamoyl radicals and pyridinium derivatives. The ortho‐methoxy group on pyridinium remodulates different types of intermolecular interactions, exhibiting an opposite trend in its influence on para versus ortho selectivity.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 3","pages":"Article e202400701"},"PeriodicalIF":2.8,"publicationDate":"2025-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143622459","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
C−H Methylthiolation/d3‐Methylthiolation of Pyrazole Skeleton via Interrupted Pummerer Reaction 中断Pummerer反应中吡唑骨架的C−H甲基硫化/d3-甲基硫化
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-03-01 DOI: 10.1002/ajoc.202400639
Haofeng Shi , Fengxia Sun , Jialiang Wu , Jiaxin He , Yuli Sun , Yunfei Du
{"title":"C−H Methylthiolation/d3‐Methylthiolation of Pyrazole Skeleton via Interrupted Pummerer Reaction","authors":"Haofeng Shi ,&nbsp;Fengxia Sun ,&nbsp;Jialiang Wu ,&nbsp;Jiaxin He ,&nbsp;Yuli Sun ,&nbsp;Yunfei Du","doi":"10.1002/ajoc.202400639","DOIUrl":"10.1002/ajoc.202400639","url":null,"abstract":"<div><div>The reaction of a series of pyrazole derivatives with DMSO/ ‐DMSO‐<em>d<sub>6</sub></em> and thionyl chloride conveniently afforded the 4‐thiolated pyrazole products under metal‐free conditions. This C−H functionalization/elelctrophilic thiolation process is postulated to involve the <em>in situ</em> generation of the electrophilic hypochlorothioite <em>via</em> interrupted Pummerer reaction, followed with the electrophilic methylthiolation of pyrazole skeleton.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 3","pages":"Article e202400639"},"PeriodicalIF":2.8,"publicationDate":"2025-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143622551","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 and Characterization of Novel Mesomorphic Chromenonapthophenathridines 新型介胚色单邻苯萘啶的合成与表征
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-03-01 DOI: 10.1002/ajoc.202400623
Marichandran Vadivel , Swamynathan K , V. A. Raghunathan , Dr. Sandeep Kumar
{"title":"Synthesis and Characterization of Novel Mesomorphic Chromenonapthophenathridines","authors":"Marichandran Vadivel ,&nbsp;Swamynathan K ,&nbsp;V. A. Raghunathan ,&nbsp;Dr. Sandeep Kumar","doi":"10.1002/ajoc.202400623","DOIUrl":"10.1002/ajoc.202400623","url":null,"abstract":"<div><div>Heterocyclic discotic liquid crystals containing heteroatoms such as O, N, S, Se, P as part of π‐conjugated framework has revolutionized organic semiconductors research. The presence of heteroatom in π‐conjugated core has been reported to strikingly influence the self‐assembling properties. In this work we have synthesized novel chromenophenanthridines where the incorporation of oxygen facilitates the in plane ordering of central core and improves liquid crystalline character in these molecules. This paper elucidates the mesomorphic behavior of chromenonapthophenanthridines prepared via tandem Pictet Spengler cyclisation and ipso‐aromatic substitution in one pot. The synthesized compounds exhibited wide range enantiotropic columnar hexagonal phase. The mesomorphic behavior was suggested as a function of peripheral alkyl chains. The shorter homologue was found to exhibit hexagonal columnar plastic phase whereas higher ones exhibit hexagonal columnar phase.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 3","pages":"Article e202400623"},"PeriodicalIF":2.8,"publicationDate":"2025-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143622568","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
Indenoindenes, Indenoindoles, and Indenobenzofurans via the Interrupted iso‐Nazarov Reaction 茚二酚、茚二酚和茚二苯并呋喃通过中断异-纳扎罗夫反应
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-03-01 DOI: 10.1002/ajoc.202400655
Sineenart Attanonchai , Kasam Poonswat , Prof. Dr. Somsak Ruchirawat , Dr. Poonsakdi Ploypradith
{"title":"Indenoindenes, Indenoindoles, and Indenobenzofurans via the Interrupted iso‐Nazarov Reaction","authors":"Sineenart Attanonchai ,&nbsp;Kasam Poonswat ,&nbsp;Prof. Dr. Somsak Ruchirawat ,&nbsp;Dr. Poonsakdi Ploypradith","doi":"10.1002/ajoc.202400655","DOIUrl":"10.1002/ajoc.202400655","url":null,"abstract":"<div><div>The cascade carbocation cyclization (CCC) of the secondary benzylic, or the benzhydryl, carbocation by the 2‐indene, 2/3‐indole, or 2/3‐benzofuran followed by the intermolecular nucleophilic addition by H‐/allyl‐silane or electron‐rich arenes, also classifiable as the interrupted <em>iso</em>‐Nazarov reaction, provided the corresponding indane‐fused indane/indole/benzofuran scaffolds. The initial CCC forged the <em>trans</em> relationship at the two newly formed adjacent stereogenic centers while the latter provided the selective <em>cis</em> stereocontrol at the new ring junction. Starting from achiral alcohols, the reaction sequence furnished the oxygen/nitrogen‐containing indane fused‐ring tetracyclic systems in moderate to good yields with excellent stereoselectivity on all three contiguous chiral centers.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 3","pages":"Article e202400655"},"PeriodicalIF":2.8,"publicationDate":"2025-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143622343","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 a Bis‐Boron/Sulfur Doped Ullazine and Direct Comparison with Its Boron/Nitrogen and Boron/Oxygen Analogues 双硼/硫掺杂Ullazine的合成及其硼/氮和硼/氧类似物的直接比较
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-03-01 DOI: 10.1002/ajoc.202400637
Ruijun Jiang , Tingting Qin , Yiping Wang , Huicong Cui , Yanping Shi , Lei Zhang , Dr. Xuguang Liu
{"title":"Synthesis of a Bis‐Boron/Sulfur Doped Ullazine and Direct Comparison with Its Boron/Nitrogen and Boron/Oxygen Analogues","authors":"Ruijun Jiang ,&nbsp;Tingting Qin ,&nbsp;Yiping Wang ,&nbsp;Huicong Cui ,&nbsp;Yanping Shi ,&nbsp;Lei Zhang ,&nbsp;Dr. Xuguang Liu","doi":"10.1002/ajoc.202400637","DOIUrl":"10.1002/ajoc.202400637","url":null,"abstract":"<div><div>Ullazine, a typical polycyclic aromatic hydrocarbon with a 14 π‐electron nitrogen‐containing core, has garnered significant attention due to its excellent performance in optoelectronics applications. Integration of heteroatoms into the frameworks of polycyclic aromatic hydrocarbons is a well‐established strategy for modifying molecular characteristics and functionalities. In this study, heteroatom‐doped ullazine congener <strong>Bis‐BS‐U</strong> containing two boron‐sulfur bonds was synthesized. The structures and properties of <strong>Bis‐BS‐U</strong> were systematically compared to those of the previously reported bis‐boron/nitrogen doped ullazine (<strong>Bis‐BN‐U</strong>) and bis‐boron/oxygen doped ullazine (<strong>Bis‐BO‐U</strong>). Notably, the absorption and fluorescence spectra of <strong>Bis‐BS‐U</strong> exhibited a pronounced red shift relative to those of <strong>Bis‐BN‐U</strong> and <strong>Bis‐BO‐U</strong>. Theoretical calculations suggest that the boron/sulfur six‐member ring in <strong>Bis‐BS‐U</strong> exhibits very weak antiaromaticity. Moreover, the fluorescence intensity of <strong>Bis‐BS‐U</strong> showed an initial increase upon addition of Hg<sup>2+</sup>, followed by gradual decrease over time. This study expands the family of ullazine and provides valuable insights for the future development of heteroatom‐doped ullazines.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 3","pages":"Article e202400637"},"PeriodicalIF":2.8,"publicationDate":"2025-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143622449","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
Transition Metal‐Catalyzed Transformations of Oxa/Aza Bicyclic Alkenes 过渡金属催化氧杂双环烯烃的转化
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-03-01 DOI: 10.1002/ajoc.202400617
Fatemeh Doraghi , Shahab Kermaninia , Hadi Afaridoun , Bagher Larijani , Mohammad Mahdavi
{"title":"Transition Metal‐Catalyzed Transformations of Oxa/Aza Bicyclic Alkenes","authors":"Fatemeh Doraghi ,&nbsp;Shahab Kermaninia ,&nbsp;Hadi Afaridoun ,&nbsp;Bagher Larijani ,&nbsp;Mohammad Mahdavi","doi":"10.1002/ajoc.202400617","DOIUrl":"10.1002/ajoc.202400617","url":null,"abstract":"<div><div>Transition metal‐catalyzed transformations of bridged‐ring bicyclic alkenes have emerged as an interesting area of synthetic chemistry in the last two decades. Due to their multiple points of reactivity, bicyclic alkenes, especially <em>oxa</em>/<em>aza</em>‐bicyclic alkenes, can participate in a variety annulation/functionalization reactions catalyzed by transition metals. In this review, a wide range of transition metal‐catalyzed C−H activation/addition of bicyclic alkenes with nucleophiles is described.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 3","pages":"Article e202400617"},"PeriodicalIF":2.8,"publicationDate":"2025-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143622552","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
One‐Pot Synthesis of Polysubstituted Indoles via the Indium‐Promoted Regioselective Hydrohydrazination of Terminal Alkynes 末端炔的铟促进区域选择性氢化一锅法合成多取代吲哚
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-03-01 DOI: 10.1002/ajoc.202400682
Norio Sakai , Takahiro Yokoyama , Kento Ishida
{"title":"One‐Pot Synthesis of Polysubstituted Indoles via the Indium‐Promoted Regioselective Hydrohydrazination of Terminal Alkynes","authors":"Norio Sakai ,&nbsp;Takahiro Yokoyama ,&nbsp;Kento Ishida","doi":"10.1002/ajoc.202400682","DOIUrl":"10.1002/ajoc.202400682","url":null,"abstract":"<div><div>We demonstrated that indium bromide, a trivalent indium compound with strong tolerance toward various coordination functional groups, can be used as a sole promotor to effectively promote the hydrohydrazination of a variety of <em>N</em>‐phenylhydrazines with aromatic/aliphatic alkynes and the subsequent [3,3]‐sigmatropic reaction of the hydrazone intermediate, leading to the one‐pot preparation of various poly‐substituted indole derivatives. Notably, the initial hydrohydrazination proceeded in a Markovnikov‐type manner and showed high regioselectivity, with the hydrohydrazination of arylalkynes affording only 2‐arylindole derivatives. Therefore, our findings provide a facile and practical one‐pot process for the synthesis of polysubstituted indole derivatives from various phenylhydrazines and aromatic/aliphatic alkynes using only one promotor.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 3","pages":"Article e202400682"},"PeriodicalIF":2.8,"publicationDate":"2025-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ajoc.202400682","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143622637","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
C–Centered Radicals: Generation, Detection, Stability and Perspectives c中心自由基：产生、检测、稳定性和展望
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-03-01 DOI: 10.1002/ajoc.202400686
Dr. Archana Velloth , Piyush Kumar , Shabana Butt , Dr. Sugumar Venkataramani
{"title":"C–Centered Radicals: Generation, Detection, Stability and Perspectives","authors":"Dr. Archana Velloth ,&nbsp;Piyush Kumar ,&nbsp;Shabana Butt ,&nbsp;Dr. Sugumar Venkataramani","doi":"10.1002/ajoc.202400686","DOIUrl":"10.1002/ajoc.202400686","url":null,"abstract":"<div><div><em>C–</em>Centered radicals are one of the classical reactive intermediates that have shown enormous utility in organic synthesis. Besides homolytic bond cleavages, the advancements of electron transfer‐based photoredox and electroredox processes are popular choices for their generation and synthetic explorations. Considering the widespread attention and versatility of <em>C</em>‐centered radicals in several fields, a systematic understanding of structural, stability, and reactivity aspects is crucial for the further development and futuristic applications of radical chemistry. In this regard, several topics pertaining to the generation, detection, and studies relevant to radical chemistry in general and thermodynamic and kinetic stability of the <em>C</em>‐centered radicals specifically, with a major emphasis on physical organic chemistry aspects, are presented. Besides portraying the factors governing their stability and reactivity, this contribution also discusses their challenges and perspectives.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 3","pages":"Article e202400686"},"PeriodicalIF":2.8,"publicationDate":"2025-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143622727","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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