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Asian Journal of Organic Chemistry最新文献

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Experiment and Computational Study on Pd‐Catalyzed MIA‐Directed Ortho‐C−H Alkynlation of Phenylalanine 钯催化 MIA 引导的苯丙氨酸正交-C-H 烷炔化实验和计算研究
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2024-07-01 DOI: 10.1002/ajoc.202400159
{"title":"Experiment and Computational Study on Pd‐Catalyzed MIA‐Directed Ortho‐C−H Alkynlation of Phenylalanine","authors":"","doi":"10.1002/ajoc.202400159","DOIUrl":"10.1002/ajoc.202400159","url":null,"abstract":"<div><p>The direct <em>ortho</em>‐alkynylation of substituted phenylalanine has been successfully achieved through methoxyiminoacyl (MIA)‐mediated Pd‐catalyzed C−H functionalization. This innovative protocol showcases the ability to apply a diverse range of phenylalanine substrates, resulting in the efficient synthesis of alkynylation benzylamine derivatives with notable effectiveness. Computational investigations further revealed that the fluoride ion enhances the electropositivity of Pd(IV) and the interaction between C1 and C2 within the transition state of the reductive elimination, which significantly expedites the reductive elimination step in the alkynylation process.</p></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 7","pages":"Article e202400159"},"PeriodicalIF":2.8,"publicationDate":"2024-07-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140931774","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 Versatile Aryliodine Synthons by Aryliodonium Rearrangement Reactions 通过芳基碘鎓重排反应合成多功能芳基碘合成物
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2024-07-01 DOI: 10.1002/ajoc.202400129
{"title":"Synthesis of Versatile Aryliodine Synthons by Aryliodonium Rearrangement Reactions","authors":"","doi":"10.1002/ajoc.202400129","DOIUrl":"10.1002/ajoc.202400129","url":null,"abstract":"<div><p>The excellent reactivity of diaryliodonium salts has primarily been attributed to the efficient departure of the iodoarene unit, facilitating a variety of arylation reactions. However, one equivalent of iodoarene as a side‐product is a chemical waste in these reactions, which was criticized by chemists for hindering its popularity. Recently, the development of synthetic methodology that preserve the aryl iodine moiety received increasing attention. Oxidative rearrangement reactions involving aryliodonium reagents have significantly addressed the atom‐economic issue, thereby broadening the reaction scope. The resulting intricate aryliodine products are viewed as valuable synthons for the synthesis of natural products, pharmaceutical intermediates and other fine chemicals.</p></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 7","pages":"Article e202400129"},"PeriodicalIF":2.8,"publicationDate":"2024-07-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140932127","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
Polyhalogenated 2‐Azabicyclo[2.2.1]heptanes from Polyhaloaldimines and Cyclopentadiene via Cycloaddition and Wagner‐Meerwein Rearrangement 通过环加成和瓦格纳-梅尔韦恩重排从多卤代醛亚胺和环戊二烯制备多卤代 2-氮杂双环[2.2.1]庚烷
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2024-07-01 DOI: 10.1002/ajoc.202400017
{"title":"Polyhalogenated 2‐Azabicyclo[2.2.1]heptanes from Polyhaloaldimines and Cyclopentadiene via Cycloaddition and Wagner‐Meerwein Rearrangement","authors":"","doi":"10.1002/ajoc.202400017","DOIUrl":"10.1002/ajoc.202400017","url":null,"abstract":"<div><p>2‐Arylsulfonyl‐2‐azabicyclo[<em>2.2.1</em>]hept‐5‐enes, synthesized via the cycloaddition of chloral‐ or dichloro(phenyl)acetaldehyde <em>N</em>‐arylsulfonylimines to cyclopentadiene, undergo Wagner‐Meerwein rearrangement under the action of bromine or chlorine to afford 3‐polychloro‐6,7‐dyhalogenated 2‐arylsulfonylazabicyclo[<em>2.2.1</em>]heptanes.</p></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 7","pages":"Article e202400017"},"PeriodicalIF":2.8,"publicationDate":"2024-07-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140204534","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
Stereoselective Synthesis of Polysubstituted Tetrahydropyrans by Brønsted Acid‐Mediated Hydroxyalkoxylation of Silylated Alkenols 通过酸介导的环化反应，无金属立体选择性合成带有相邻四级和三级立体中心的四氢吡喃
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2024-07-01 DOI: 10.1002/ajoc.202400096
{"title":"Stereoselective Synthesis of Polysubstituted Tetrahydropyrans by Brønsted Acid‐Mediated Hydroxyalkoxylation of Silylated Alkenols","authors":"","doi":"10.1002/ajoc.202400096","DOIUrl":"10.1002/ajoc.202400096","url":null,"abstract":"<div><p>A convenient route for the preparation of tetrahydropyran (THP) derivatives with a quaternary and tertiary vicinal stereocenters is reported. The atom economy acid‐catalyzed cyclization of allylsilyl alcohols provided polysubstituted tetrahydropyrans in good yields and excellent diastereoselectivities (&gt;95 : 5). In comparison with the traditional oxymercuration procedure, this approach resulted to be more efficient in both yield and stereocontrol.</p></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 7","pages":"Article e202400096"},"PeriodicalIF":2.8,"publicationDate":"2024-07-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ajoc.202400096","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140579951","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
Palladium‐Catalyzed Carbonylation of Aryl Sulfonium Salts with CO2 as a CO Surrogate 钯催化的芳基锍盐与 CO2 作为 CO 代用品的羰基化反应
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2024-07-01 DOI: 10.1002/ajoc.202400142
{"title":"Palladium‐Catalyzed Carbonylation of Aryl Sulfonium Salts with CO2 as a CO Surrogate","authors":"","doi":"10.1002/ajoc.202400142","DOIUrl":"10.1002/ajoc.202400142","url":null,"abstract":"<div><p>Palladium‐catalyzed carbonylation of aryl sulfonium salts with CO<sub>2</sub> as a CO surrogate has been successfully developed via a one‐pot two‐step procedure. Thus, by merging thianthrenation and the carbonylation, site‐selective aromatic C−H carbonylation of a plethora of readily available arenes can be realized with CO<sub>2</sub>, providing access to a variety of structurally diverse and useful benzamides, esters and carboxylic acids. Simple operation, broad substrate scope, good functional group tolerance and mild reaction conditions are the attractive features of the method. Late‐stage functionalization of complex bioactive molecules as well as the precise synthesis of pharmaceuticals 1‐BCP and butoxycaine demonstrated the potential application of the established protocol.</p></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 7","pages":"Article e202400142"},"PeriodicalIF":2.8,"publicationDate":"2024-07-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140580101","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
Mild and Catalyst‐Free Phosphination of Isocyanates with [TBA][P(SiCl3)2] for the Synthesis of Phosphinecarboxamides 用 [TBA][P(SiCl3)2]温和且无催化剂地磷化异氰酸酯以合成膦甲酰胺
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2024-07-01 DOI: 10.1002/ajoc.202400178
{"title":"Mild and Catalyst‐Free Phosphination of Isocyanates with [TBA][P(SiCl3)2] for the Synthesis of Phosphinecarboxamides","authors":"","doi":"10.1002/ajoc.202400178","DOIUrl":"10.1002/ajoc.202400178","url":null,"abstract":"<div><p>A procedure utilizing [TBA][P(SiCl<sub>3</sub>)<sub>2</sub>] as P source for the synthesis of phosphinecarboxamides is presented. The synthesis involves the reaction of [TBA][P(SiCl<sub>3</sub>)<sub>2</sub>] with isocyanates. These compounds act as highly effective reagents for the subsequent phosphination of isocyanates, leading to the formation of phosphine(triscarboxamides). This reaction proceeds swiftly under mild and straightforward conditions, making it suitable for a wide range of commercially available isocyanates.</p></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 7","pages":"Article e202400178"},"PeriodicalIF":2.8,"publicationDate":"2024-07-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140839443","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 3‐Aryl Substituted Triimidazotriazines via Regioselective Direct Arylation 通过区域选择性直接芳基化合成 3-芳基取代的三咪唑三嗪
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2024-07-01 DOI: 10.1002/ajoc.202400082
{"title":"Synthesis of 3‐Aryl Substituted Triimidazotriazines via Regioselective Direct Arylation","authors":"","doi":"10.1002/ajoc.202400082","DOIUrl":"10.1002/ajoc.202400082","url":null,"abstract":"<div><p>A general and convenient selective direct arylation of the 3‐position of triimidazo[1,2‐a:1’,2’‐c:1’’,2’’‐e][1,3,5]triazine (<strong>1</strong>) with (hetero)aryl halides in DMA was successfully achieved in the presence of K<sub>2</sub>CO<sub>3</sub> as the base and a catalyst precursor consisting of Pd(OAc)<sub>2</sub> and P(2‐furyl)<sub>3</sub>. Electron‐poor and ‐rich (hetero)aryl moieties, including the strongly deactivated and sterically encumbered 2,4,6‐trimethoxyphenyl unit, are well tolerated in the electrophilic partner. The data obtained in this synthetic study support a reaction mechanism involving an electrophilic attack of an arylpalladium‐(II) halide species onto the triazine ring.</p></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 7","pages":"Article e202400082"},"PeriodicalIF":2.8,"publicationDate":"2024-07-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140602580","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
Biphenylene and 1‐Azabiphenylene as a Platform for Synthesis of Azapolyaromatic Compounds 以联苯和 1-Azabiphenylene 为平台合成偶氮芳香族化合物
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2024-07-01 DOI: 10.1002/ajoc.202400126
{"title":"Biphenylene and 1‐Azabiphenylene as a Platform for Synthesis of Azapolyaromatic Compounds","authors":"","doi":"10.1002/ajoc.202400126","DOIUrl":"10.1002/ajoc.202400126","url":null,"abstract":"<div><p>Attempts to carry out intramolecular annulation of 9,10‐diarylbenzo[<em>h</em>]quinolines and 9,10‐di(hetero)arylphenanthrenes to aromatics with expanded π‐conjugated systems by using different methods are described. The starting compounds (9,10‐diarylbenzo[<em>h</em>]quinolines and 9,10‐di(hetero)arylphenanthrenes) were prepared by C−C bond activation in 1‐azabiphenylene or biphenylene followed by insertion of internal alkynes. Interestingly, unlike in purely carbon‐based aromatics, the course of the annulation turned out to be highly dependent on the structure of maternal compounds. In a handful of cases were obtained the expected or desired products. In others, unexpected rearrangements of the basic molecular frameworks were observed.</p></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 7","pages":"Article e202400126"},"PeriodicalIF":2.8,"publicationDate":"2024-07-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ajoc.202400126","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140625583","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
Total Synthesis of Eutyscoparol A and Violaceoid C Eutyscoparol A 和 Violaceoid C 的全合成
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2024-07-01 DOI: 10.1002/ajoc.202400148
{"title":"Total Synthesis of Eutyscoparol A and Violaceoid C","authors":"","doi":"10.1002/ajoc.202400148","DOIUrl":"10.1002/ajoc.202400148","url":null,"abstract":"<div><p>The total syntheses of eutyscoparol A and violaceoid C <em>via</em> violaceoid A, have been accomplished including the improved total syntheses of violaceoid A and violaceoid B. This synthetic method, which employed the desymmetrization of a symmetric diol, enabled divergent access to other violaceoids, eutyscoparols, and their derivatives.</p></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 7","pages":"Article e202400148"},"PeriodicalIF":2.8,"publicationDate":"2024-07-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ajoc.202400148","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140656488","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
Photocatalytic (V2O5/TiO2) Blue LED Mediated Selective Oxidation of Alcohols, Styrene to Aldehydes, and Oxygenation of Alkyl‐Benzene to Ketones 光催化（V2O5/二氧化钛）蓝光 LED 介导的醇、苯乙烯到醛的选择性氧化，以及烷基苯到酮的氧合反应
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2024-07-01 DOI: 10.1002/ajoc.202400088
{"title":"Photocatalytic (V2O5/TiO2) Blue LED Mediated Selective Oxidation of Alcohols, Styrene to Aldehydes, and Oxygenation of Alkyl‐Benzene to Ketones","authors":"","doi":"10.1002/ajoc.202400088","DOIUrl":"10.1002/ajoc.202400088","url":null,"abstract":"<div><p>The development of a low‐cost, reusable, and sustainable approach is a difficult and emerging demand in the coming arena. Here, we demonstrate the selective oxidation of primary alcohol, styrene to aldehyde, and alkyl benzene to appropriate ketone, under Blue LED irradiation. The developed approaches employ reusable catalysts (V<sub>2</sub>O<sub>5</sub>/TIO<sub>2</sub>) and green solvents (ACN, H<sub>2</sub>O) at room temperature. The substrate scope is widely investigated for various compounds of different functionalities. Organic transformations are supported by reaction mechanistic studies. The gram scale reaction and catalytic recyclability were also carried out to maximize the protocol's synthetic utility.</p></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 7","pages":"Article e202400088"},"PeriodicalIF":2.8,"publicationDate":"2024-07-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140580210","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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