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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 Q1 CHEMISTRY, ORGANIC Pub Date : 2024-07-01 DOI: 10.1002/ajoc.202400159

The direct ortho‐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.

通过甲氧基亚氨基酰基(MIA)介导的钯催化 C-H 功能化,成功实现了取代苯丙氨酸的直接正炔化。这一创新方案展示了应用多种苯丙氨酸底物的能力,从而高效合成了炔化苄胺衍生物。计算研究进一步发现,氟离子增强了钯(IV)的电正性以及还原消除过渡态中 C1 和 C2 之间的相互作用,从而大大加快了炔化过程中的还原消除步骤。
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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 Q1 CHEMISTRY, ORGANIC Pub Date : 2024-07-01 DOI: 10.1002/ajoc.202400129

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.

二芳基碘鎓盐具有出色的反应活性,这主要归功于碘芳烃单元的高效离去,从而促进了各种芳基化反应。然而,在这些反应中,作为副产物的一当量碘芳烃是一种化学废物,化学家们批评这阻碍了碘芳烃的普及。最近,能保留芳基碘分子的合成方法的开发受到越来越多的关注。涉及芳基碘试剂的氧化重排反应极大地解决了原子经济性问题,从而拓宽了反应范围。由此产生的复杂的芳基碘产品被视为合成天然产品、医药中间体和其他精细化学品的宝贵合成物。
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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 Q1 CHEMISTRY, ORGANIC Pub Date : 2024-07-01 DOI: 10.1002/ajoc.202400017

2‐Arylsulfonyl‐2‐azabicyclo[2.2.1]hept‐5‐enes, synthesized via the cycloaddition of chloral‐ or dichloro(phenyl)acetaldehyde N‐arylsulfonylimines to cyclopentadiene, undergo Wagner‐Meerwein rearrangement under the action of bromine or chlorine to afford 3‐polychloro‐6,7‐dyhalogenated 2‐arylsulfonylazabicyclo[2.2.1]heptanes.

2- 芳基磺酰基-2-氮杂双环[2.2.1]庚-5-烯是通过氯醛或二氯(苯基)乙醛 N-芳基磺酰亚胺与环戊二烯的环化反应合成的,在溴或氯的作用下发生瓦格纳-梅尔韦恩重排反应,得到 3-多氯-6,7-二卤代 2-芳基磺酰基氮杂双环[2.2.1]庚烷。
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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 Q1 CHEMISTRY, ORGANIC Pub Date : 2024-07-01 DOI: 10.1002/ajoc.202400096

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 (>95 : 5). In comparison with the traditional oxymercuration procedure, this approach resulted to be more efficient in both yield and stereocontrol.

本研究报道了一种制备具有四级和三级副立体中心的四氢吡喃(THP)衍生物的简便路线。通过原子经济酸催化烯丙基硅烷醇的环化反应,可获得多取代的四氢吡喃,产率高,非对映选择性极佳(95:5)。与传统的氧巯化过程相比,这种方法在产率和立体控制方面都更为有效。
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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 Q1 CHEMISTRY, ORGANIC Pub Date : 2024-07-01 DOI: 10.1002/ajoc.202400142

Palladium‐catalyzed carbonylation of aryl sulfonium salts with CO2 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 CO2, 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.

钯催化的芳基锍盐羰基化反应以二氧化碳作为一氧化碳代用品,通过一步法两步法已成功开发出来。因此,通过合并噻蒽化合和羰基化反应,可以用 CO2 对大量易得的炔烃进行位点选择性芳香 C-H 羰基化反应,从而获得各种结构多样且有用的苯甲酰胺、酯和羧酸。该方法具有操作简单、底物范围广、官能团耐受性好和反应条件温和等诱人特点。复杂生物活性分子的后期功能化以及药物 1-BCP 和丁氧基卡因的精确合成,都证明了这一既定方案的潜在应用价值。
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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 Q1 CHEMISTRY, ORGANIC Pub Date : 2024-07-01 DOI: 10.1002/ajoc.202400178

A procedure utilizing [TBA][P(SiCl3)2] as P source for the synthesis of phosphinecarboxamides is presented. The synthesis involves the reaction of [TBA][P(SiCl3)2] 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.

本文介绍了利用 [TBA][P(SiCl3)2]作为 P 源合成膦甲酰胺的过程。合成过程包括 [TBA][P(SiCl3)2]与异氰酸酯的反应。这些化合物是异氰酸酯随后磷化的高效试剂,可生成膦(三碳酰胺)。该反应在温和直接的条件下迅速进行,因此适用于多种市售异氰酸酯。
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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 Q1 CHEMISTRY, ORGANIC Pub Date : 2024-07-01 DOI: 10.1002/ajoc.202400082

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 (1) with (hetero)aryl halides in DMA was successfully achieved in the presence of K2CO3 as the base and a catalyst precursor consisting of Pd(OAc)2 and P(2‐furyl)3. 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.

在以 K2CO3 为碱和由 Pd(OAc)2 和 P(2-呋喃)3 组成的催化剂前体存在下,成功地在 DMA 中用(杂)芳基卤化物对三咪唑并[1,2-a:1',2'-c:1'',2''-e][1,3,5]三嗪(1)的 3 位进行了一般和方便的选择性直接芳基化反应。电子贫乏和富集的(杂)芳基,包括强烈失活和立体包被的 2,4,6-三甲氧基苯基单元,都能很好地容纳在亲电伴侣中。这项合成研究获得的数据支持一种反应机理,即芳基钯(II)卤化物亲电攻击三嗪环。
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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 Q1 CHEMISTRY, ORGANIC Pub Date : 2024-07-01 DOI: 10.1002/ajoc.202400126

Attempts to carry out intramolecular annulation of 9,10‐diarylbenzo[h]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[h]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.

本文介绍了尝试采用不同方法将 9,10-二芳基苯并[h]喹啉和 9,10-二(杂)芳基菲烷分子内环化为具有扩展对偶共轭体系的芳烃。起始化合物(9,10-二芳基苯并[h]喹啉和 9,10-二(杂)芳基菲)是通过在 1- 氮杂联苯或联苯中活化 C-C 键,然后插入内部炔烃制备的。有趣的是,与纯碳基芳烃不同,环化过程在很大程度上取决于母体化合物的结构。在少数情况下,得到了预期或理想的产物。在其他情况下,基本分子框架会发生意想不到的重排。
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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 Q1 CHEMISTRY, ORGANIC Pub Date : 2024-07-01 DOI: 10.1002/ajoc.202400148

The total syntheses of eutyscoparol A and violaceoid C via 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.

我们完成了丁香油酚 A 的全合成和通过类中提琴酸 A 合成类中提琴酸 C 的全合成,包括改进了类中提琴酸 A 和类中提琴酸 B 的全合成。这种合成方法采用了不对称二元醇的非对称化技术,从而能够以不同的方法获得其他类长春花碱、丁香油醇及其衍生物。
{"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 Q1 CHEMISTRY, ORGANIC Pub Date : 2024-07-01 DOI: 10.1002/ajoc.202400088

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 (V2O5/TIO2) and green solvents (ACN, H2O) 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.

开发一种低成本、可重复使用和可持续的方法是一个难题,也是未来新出现的需求。在此,我们展示了在蓝光 LED 的照射下将伯醇、苯乙烯氧化成醛以及将烷基苯氧化成适当酮的选择性氧化方法。所开发的方法采用了可重复使用的催化剂(V2O5/TIO2)和室温下的绿色溶剂(ACN、H2O)。针对不同官能团的各种化合物,对底物范围进行了广泛研究。反应机理研究为有机转化提供了支持。此外,还进行了克级反应和催化剂可回收性研究,以最大限度地提高该方案的合成效用。
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引用次数: 0
期刊
Asian Journal of Organic Chemistry
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