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 Q1 CHEMISTRY, ORGANIC

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

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, via 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 >99 % ee and 17 : 1 dr), 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.

为合成具有生物活性和功能丰富的六氢呋喃咔唑制定一种有效的策略是一个非常理想但又要求很高的追求。这项研究阐明了一种突破性的策略，涉及由硅胶促进的意想不到的去氟羟基化反应，产生高度对映和非对映选择性的六氢呋喃咔唑框架。该方法通过氨基催化不对称远程[4+2]加成过程，形成了5个连续的手性中心，包括3个季元立体中心和1个全碳螺旋中心。开发的方法允许构建多种产品（24个示例，高达>； 99% ee和17:1 dr），反映了其显着的基板范围。此外，我们证明了克尺度合成和控制实验的可行性，这些实验强调了方法上的进步，并提供了对潜在机制的见解。

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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 Q1 CHEMISTRY, ORGANIC

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

The reaction modes in the reactions of several alkenes with Tf₂C=CH₂ (Tf=CF₃SO₂) have been controlled by the reaction solvents. For example, although the reaction with allylsilanes selectively produced normal allylation products in MeCN, gem‐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 Tf₂C=CH₂ smoothly proceeded to give the corresponding (E)‐alkenes bearing a superacidic bis(triflyl)methyl group.

几种烯烃与Tf2C=CH2 （Tf=CF3SO2）反应时的反应模式由反应溶剂控制。例如，虽然与烯丙基硅烷的反应在MeCN中选择性地产生正常的烯丙基化产物，但在甲苯中形成gem-bis（三氟基）环戊烷。特别是，（3+2）环加合物的选择性形成是通过使用位阻烯丙基硅烷实现的。我们还发现在与简单烯烃的反应中有明显的溶剂效应。也就是说，在热甲苯中，烯烃与Tf2C=CH2的Alder烯反应顺利进行，得到相应的带有超酸性二（三氟基）甲基的(E)-烯烃。

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 Q1 CHEMISTRY, ORGANIC

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

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.

利用能量分解方法对吡啶酰化和氨基甲酰化反应中区域选择性开关的来源进行了计算研究。结果表明，区域选择性的偏好来自于磷酰基/氨基甲酰基自由基与吡啶衍生物之间不同的分子间相互作用。吡啶上的邻甲氧基调节不同类型的分子间相互作用，在对对邻选择性的影响方面表现出相反的趋势。

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 Q1 CHEMISTRY, ORGANIC

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

The reaction of a series of pyrazole derivatives with DMSO/ ‐DMSO‐d₆ 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 in situ generation of the electrophilic hypochlorothioite via interrupted Pummerer reaction, followed with the electrophilic methylthiolation of pyrazole skeleton.

在无金属条件下，一系列吡唑衍生物与二甲基亚砜/-二甲基亚砜-d6 和亚硫酰氯反应，可以方便地得到 4-硫代吡唑产物。据推测，这种 C-H 功能化/亲电硫代过程是通过间断的普默尔反应在原位生成亲电的次硫代氯，然后对吡唑骨架进行亲电的甲硫醇化反应。

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 Q1 CHEMISTRY, ORGANIC

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

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.

含有杂原子（如 O、N、S、Se、P）的杂环盘状液晶是π-共轭框架的一部分，它给有机半导体研究带来了革命性的变化。据报道，π-共轭核心中杂原子的存在会显著影响自组装特性。在这项工作中，我们合成了新型铬菲啶，其中氧的加入促进了中心核的平面有序化，并改善了这些分子的液晶特性。本文阐明了通过串联皮克泰-斯宾格勒环化和同芳香族取代在一锅中制备的铬萘菲啶的介形态行为。合成的化合物呈现出宽范围的对映柱状六方相。介形行为是外围烷基链的一种功能。发现较短的同系物表现出六角柱状塑性相，而较长的同系物则表现出六角柱状相。

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 Q1 CHEMISTRY, ORGANIC

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

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 iso‐Nazarov reaction, provided the corresponding indane‐fused indane/indole/benzofuran scaffolds. The initial CCC forged the trans relationship at the two newly formed adjacent stereogenic centers while the latter provided the selective cis 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.

二级苯基或苯并羟基被2-茚、2/3-吲哚或2/3-苯并呋喃进行级联碳阳离子环化（CCC），然后被H-/烯丙基硅烷或富电子芳烃分子间亲核加成，也可归类为中断的异纳扎罗夫反应，提供了相应的茚-融合茚/吲哚/苯并呋喃支架。最初的CCC在两个新形成的相邻立体中心形成了反式关系，而后者在新的环结处提供了选择性的顺式立体控制。从非手性醇开始，该反应序列提供了含氧/氮的含烷融合环四环体系，产率中等至较高，在三个连续的手性中心上具有优异的立体选择性。

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 Q1 CHEMISTRY, ORGANIC

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

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 Bis‐BS‐U containing two boron‐sulfur bonds was synthesized. The structures and properties of Bis‐BS‐U were systematically compared to those of the previously reported bis‐boron/nitrogen doped ullazine (Bis‐BN‐U) and bis‐boron/oxygen doped ullazine (Bis‐BO‐U). Notably, the absorption and fluorescence spectra of Bis‐BS‐U exhibited a pronounced red shift relative to those of Bis‐BN‐U and Bis‐BO‐U. Theoretical calculations suggest that the boron/sulfur six‐member ring in Bis‐BS‐U exhibits very weak antiaromaticity. Moreover, the fluorescence intensity of Bis‐BS‐U showed an initial increase upon addition of Hg²⁺, 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.

乌拉嗪是一种典型的14 π电子核含氮的多环芳烃，因其在光电子学方面的优异性能而受到广泛关注。将杂原子整合到多环芳烃的框架中是一种完善的修饰分子特征和功能的策略。本研究合成了含有两个硼硫键的杂原子掺杂ullazine同源物Bis-BS-U。将Bis-BS-U的结构和性能与先前报道的双硼/氮掺杂ullazine （Bis-BN-U）和双硼/氧掺杂ullazine （Bis-BO-U）进行了系统的比较。值得注意的是，与Bis-BN-U和Bis-BO-U相比，Bis-BS-U的吸收光谱和荧光光谱出现了明显的红移。理论计算表明，Bis-BS-U中的硼硫六元环具有很弱的抗芳性。此外，Bis-BS-U的荧光强度在加入Hg2+后呈现出初始增加，随后随时间逐渐降低的趋势。该研究扩大了乌拉嗪家族，为未来杂原子掺杂乌拉嗪的发展提供了有价值的见解。

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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 Q1 CHEMISTRY, ORGANIC

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

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 oxa/aza‐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.

近二十年来，过渡金属催化的桥环双环烯转化已成为合成化学的一个有趣领域。由于双环烯，尤其是氧杂/氮杂双环烯具有多点反应活性，因此可以在过渡金属催化下参与各种环化/官能化反应。在本综述中，介绍了一系列过渡金属催化的双环烯与亲核物的 C-H 活化/加成反应。

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 Q1 CHEMISTRY, ORGANIC

Asian Journal of Organic Chemistry

Pub Date : 2025-03-01 DOI: 10.1002/ajoc.202400682

Norio Sakai , Takahiro Yokoyama , Kento Ishida

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 N‐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.

我们证明了溴化铟是一种对各种配位官能团具有较强耐受性的三价铟化合物，可以作为唯一启动子有效地促进多种n -苯基肼与芳香/脂肪炔的氢化反应以及随后的腙中间体的[3,3]-异位反应，从而一锅制得多种多取代吲哚衍生物。值得注意的是，初始的氢化反应以markovnikov型方式进行，并表现出很高的区域选择性，芳基炔的氢化反应只产生2-芳基环唑衍生物。因此，我们的研究结果提供了一种简单实用的一锅法，仅使用一个启动子就可以从各种苯基肼和芳香/脂肪炔合成多取代吲哚衍生物。

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 Q1 CHEMISTRY, ORGANIC

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

C–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 C‐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 C‐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.

c中心自由基是一种经典的反应中间体，在有机合成中有着广泛的应用。除了均裂键外，基于电子转移的光氧化还原和电氧化还原过程的进展是其生成和合成探索的热门选择。考虑到c中心自由基在多个领域的广泛关注和多功能性，对其结构、稳定性和反应性方面的系统理解对于自由基化学的进一步发展和未来应用至关重要。在这方面，介绍了几个与自由基化学产生、检测和研究相关的主题，特别是c中心自由基的热力学和动力学稳定性，主要侧重于物理有机化学方面。除了描述控制其稳定性和反应性的因素外，本文还讨论了它们的挑战和前景。

引用次数: 0

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