European Journal of Organic Chemistry最新文献

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Perylene Based Twisted Emissive Curved Nanographene Synthesis through Scholl Reaction 通过烁尔反应合成基于苝的扭转发射型弯曲纳米石墨烯

IF 2.8 3区化学 Q2 CHEMISTRY, ORGANIC

European Journal of Organic Chemistry

Pub Date : 2024-10-21 DOI: 10.1002/ejoc.202401170

Siddhartha Samanta, Sahina Khatun, Sanhita Maity, Anirban Pradhan

A twisted chiral nanographene (NG) surrounded by eight bulky tert-butyl groups fused with emissive chromophore perylene was synthesized by highly regioselective cyclodehydrogenation strategy in which a double [6]helicene was formed simultaneously. The twisted 4-meso was unambiguously confirmed by single crystal X-ray analysis. The NG showed an excellent photoluminescence quantum yield (φf) of 55%, indicating its great potential for chiral optoelectronics.

通过高区域选择性环化氢化策略合成了一种由八个笨重的叔丁基环绕的扭曲手性纳米石墨烯（NG），并与发射性发色团苝融合，同时形成了双 [6] 螺旋烯。通过单晶 X 射线分析，明确地确认了扭曲的 4-meso。该 NG 的光致发光量子产率 (φf) 高达 55%，显示了其在手性光电子学方面的巨大潜力。

引用次数: 0

Stable Ditriflates of D-Glucose in the Synthesis of Iminosugars and Polyhydroxylated Pipecolic Acids 在合成氨基糖和多羟基联哌啶酸过程中稳定的 D-葡萄糖二硝酸盐

IF 2.5 3区化学 Q2 CHEMISTRY, ORGANIC

European Journal of Organic Chemistry

Pub Date : 2024-10-21 DOI: 10.1002/ejoc.202400395

Rosalino Balo, Andrés Fernández, David Reza, Pablo López, George W. J. Fleet, Ramón J. Estévez, Juan C. Estévez

A synthesis of the five membered iminosugar DAB and a divergent synthesis of the six membered iminosugar 1-dehydromannojirimycin (DMJ) and the corresponding sugar imino acid are reported. They involve double nucleophilic displacements of a D-xylose ditriflate by benzyl carbazate and a D-glucose ditriflate by allyl amine, respectively. They are followed by a similar protocol consisting of hydrolysis and oxidation or reduction of the resulting bicyclic glycosides. This allowed DMJ to be obtained from the cheap sugar D-glucose.

本研究报道了亚氨基糖 DAB 的合成以及 1-脱氢丹诺尻霉素（DMJ）和相应哌啶醇酸的歧化合成。关键步骤包括肼基羧酸苄酯和烯丙基胺分别对 D-木糖二呋喃酸酯和 D-葡萄糖二呋喃酸酯的双亲核置换。然后对生成的双环苷进行水解、氧化或还原。

引用次数: 0

Photocatalytic Regioselective Tandem Cyclization Protocol to Trifluoromethylated Pyrrolidones 三氟甲基化吡咯烷酮的光催化区域选择性串联环化协议

IF 2.8 3区化学 Q2 CHEMISTRY, ORGANIC

European Journal of Organic Chemistry

Pub Date : 2024-10-21 DOI: 10.1002/ejoc.202401023

Panpan Wang, Yuting Leng, Kaixia Sui, Shiliang Jiang, Ning Ma, Yangjie Wu

A new environmentally friendly and efficient strategy for preparing trifluoromethylated pyrrolidones has been developed. The process involves using visible light to induce radical cyclization of 1,5-dienes with CF3SO2Na, resulting in excellent regioselectivity. This method uses less expensive and easy-to-store trifluoromethylation reagents, making it an attractive option. Additionally, the resulting trifluoromethylated pyrrolidones can be easily modified and preliminary mechanistic studies have been presented.

我们开发出了一种制备三氟甲基化吡咯烷酮的新型环境友好型高效策略。该方法是利用可见光诱导 1,5 二烯与 CF3SO2Na 发生自由基环化反应，从而获得极佳的区域选择性。这种方法使用的三氟甲基化试剂成本较低且易于储存，因此是一种极具吸引力的选择。此外，所得到的三氟甲基化吡咯烷酮可以很容易地进行改性，初步的机理研究已经完成。

引用次数: 0

Activation of Alkenes via Chalcogen Bond: Chalcogen•••π Bond Catalyzed the Diels-Alder Reaction of 2-Vinylindoles 通过查尔根键活化烯烃：查尔根--π键催化 2-乙烯基吲哚的 Diels-Alder 反应

IF 2.8 3区化学 Q2 CHEMISTRY, ORGANIC

European Journal of Organic Chemistry

Pub Date : 2024-10-21 DOI: 10.1002/ejoc.202401102

Chang Zhao, Mengmeng Wang, Yanli Zeng

Chalcogen bond catalysis is a promising catalytic strategy, characterized by its environmental friendliness, relatively inexpensive cost, and similar reactivity to transition metal catalysis. Experimental results suggest that the S•••π and Se•••π bonds can efficiently drive the vinyl-indole-based Diels-Alder reaction (Angew. Chem. Int. Ed. 2021, 60, 9395-9400). In this work, chalcogen bond catalysis in the Diels-Alder reaction between 2-vinylindoles has been investigated based on density functional theory. For this reaction, the Te•••π bond catalysis is as an alternative catalytic strategy. The Diels-Alder reaction catalyzed by chalcogen bond is stepwise and involves two steps: the carbon–carbon bond formation process and the cyclization process. The cyclization process is the rate-determining step. From the perspective of energy decomposition analysis, the electrostatic interaction is the main factor to cause Se•••π bond catalysis, the polarization interaction is the main factor to cause Te•••π bond catalysis. Additionally, this catalytic reaction involves the endo pathway and exo pathway. The Gibbs free energy barrier values of the endo pathway are lower than those of the exo pathway, which facilitates the formation of the endo product. This study will provide a valuable perspective on the application of chalcogen bond in the activation of alkenes.

钙原键催化是一种前景广阔的催化策略，其特点是对环境友好、成本相对低廉以及与过渡金属催化相似的反应活性。实验结果表明，S--π和Se--π键可以有效地驱动乙烯基吲哚的Diels-Alder反应（Angew.）在这项工作中，基于密度泛函理论研究了 2-乙烯基吲哚之间 Diels-Alder 反应中的查耳酮键催化作用。在该反应中，Te--π键催化是一种可供选择的催化策略。由钙原键催化的 Diels-Alder 反应是逐步进行的，包括两个步骤：碳-碳键形成过程和环化过程。环化过程是决定反应速率的步骤。从能量分解的角度分析，静电作用是导致Se--π键催化的主要因素，极化作用是导致Te--π键催化的主要因素。此外，该催化反应还涉及内生途径和外生途径。内生途径的吉布斯自由能势垒值低于外生途径，这有利于内生产物的形成。这项研究将为在烯烃活化过程中应用铬化键提供一个有价值的视角。

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引用次数: 0

Rhodium(II)-Catalyzed Denitrogenative Transformations of N-Sulfonyl-1,2,3-triazoles 铑（II）催化的 N-磺酰基-1,2,3-三唑的脱氮转化

IF 2.8 3区化学 Q2 CHEMISTRY, ORGANIC

European Journal of Organic Chemistry

Pub Date : 2024-10-21 DOI: 10.1002/ejoc.202401040

Mohammad Mahdavi, Fatemeh Doraghi, Mohammad Hossein Morshedsolouk, Samaneh Ghofrani, Bagher Larijani

N-Sulfonyl-1,2,3-triazoles are valuable precursors for the generation of α-imino carbene intermediates in the presence of the metal catalysts, especially rhodium(II) complexes. Due to the presence of electrophilic carbene and nucleophilic nitrogen, these reactive intermediates can easily be incorporated into many annulations, cycloadditions, C-H or O/N/S-H bond insertions and functionalization reactions. A large number of pharmaceutically important nitrogen-based building blocks can be constructed via this direct and atom-economical carbene strategy. In this review, we have described the transformations of N-sulfonyl-1,2,3-triazoles based on α-imino rhodium(II) carbene intermediates.

N-磺酰基-1,2,3-三唑是在金属催化剂，特别是铑（II）络合物存在下生成α-亚氨基碳烯中间体的重要前体。由于亲电碳氮和亲核氮的存在，这些活性中间体可以很容易地加入到许多环化、环加成、C-H 或 O/N/S-H 键插入和官能化反应中。通过这种直接且原子经济的碳烯策略，可以构建大量具有重要药用价值的氮基构筑基块。在本综述中，我们介绍了基于α-亚氨基铑（II）碳烯中间体的 N-磺酰基-1,2,3-三唑的转化。

引用次数: 0

Front Cover: Unleashing the Power of Domino Reactions on Carbohydrates: State of the Art (Eur. J. Org. Chem. 39/2024) 封面：释放碳水化合物多米诺反应的力量：技术现状（欧洲分子化学杂志 39/2024）

IF 2.5 3区化学 Q2 CHEMISTRY, ORGANIC

European Journal of Organic Chemistry

Pub Date : 2024-10-21 DOI: 10.1002/ejoc.202483901

Giulia Antonini, Laura Petrosilli, Ilaria Giussani, Maria Gessica Ciulla, Sarah Mazzotta, Giuseppe D'Orazio

The Front Cover shows domino transformations, which play a crucial role as chemical tools in drug discovery processes. In their Review (DOI: 10.1002/ejoc.202400511), S. Mazzotta, G. D'Orazio and co-workers showcase various instances of domino transformations applied to carbohydrates, with the goal of summarizing their chemical potential in producing sugar-derived compounds. These compounds have significant applications in generating new chemical scaffolds for drug discovery and chemical biology.

封面展示了多米诺骨牌转化，它作为化学工具在药物发现过程中发挥着至关重要的作用。在他们的综述（DOI: 10.1002/ejoc.202400511）中，S. Mazzotta、G. D'Orazio 及其合作者展示了应用于碳水化合物的各种多米诺骨牌转化实例，目的是总结它们在生产糖类衍生化合物方面的化学潜力。这些化合物在为药物发现和化学生物学提供新的化学支架方面具有重要的应用价值。

引用次数: 0

Computation-Guided Scope Exploration of a Conjugate Addition/Truce-Smiles Cascade Reaction for Scaffold Diversification 计算引导下的共轭物加成/Truce-Smiles 级联反应范围探索，实现支架多样化

IF 2.8 3区化学 Q2 CHEMISTRY, ORGANIC

European Journal of Organic Chemistry

Pub Date : 2024-10-21 DOI: 10.1002/ejoc.202400870

Brendan Horst, Leopoldo J. Gabella Carena, Michael T. Doppert, Rens Ham, Thomas Hansen, Eelco Ruijter

Based on the successful application of a nitroaryl transfer cascade reaction in the total synthesis of various monoterpene indole alkaloids proceeding via fused bicyclic intermediate, we investigated analogous cascade reactions involving spiro, bridged, and alternatively fused bicyclic intermediates. Unfortunately, none of these was found to afford the desired nitroaryl transfer product. DFT studies of the original cascade process revealed that the Truce-Smiles rearrangement is the rate-determining step. In addition, we found that the subsequent SO2 extrusion is accompanied by retro-Mannich ring opening, resulting in a stabilized enolate that only recyclizes after activation of the cyclic imine moiety. Computation of the reaction profiles of the proposed alternative cascade reactions showed that the barrier for the Truce-Smiles rearrangement is unreasonably high for the bridged and alternatively fused systems, but only moderately higher for the five-membered spiro system. Reasoning that even more electron-deficient arenesulfonamides should have a lower barrier for the Truce-Smiles rearrangement, we synthesized the corresponding 2,4-dinitrobenzenesulfonamide precursor and found that it indeed smoothly undergoes the nitroaryl transfer cascade at room temperature. In this case, however, the cascade reaction produces a cyclic imine product, as the intermediate 2,4-dinitrophenyl-substituted enolate is insufficiently nucleophilic to undergo the Mannich cyclization.

基于硝基芳基转移级联反应在通过融合双环中间体全合成各种单萜吲哚生物碱中的成功应用，我们研究了涉及螺、桥和替代融合双环中间体的类似级联反应。遗憾的是，我们没有发现其中任何一种反应能产生所需的硝基芳基转移产物。对原始级联反应过程的 DFT 研究表明，Truce-Smiles 重排是决定反应速率的步骤。此外，我们还发现随后的 SO2 挤压伴随着逆曼尼希环的打开，产生了稳定的烯醇，只有在环状亚胺分子活化后才会再循环。对所提出的替代级联反应的反应曲线的计算表明，对于桥接和替代融合体系，Truce-Smiles 重排的障碍高得不合理，但对于五元螺环体系，障碍仅略微高一些。因此，我们合成了相应的 2,4-二硝基苯磺酰胺前体，并发现它确实能在室温下顺利进行硝基芳基转移级联反应。不过，在这种情况下，级联反应会产生环状亚胺产物，因为中间的 2,4-二硝基苯基取代的烯醇亲核性不足，无法进行曼尼希环化反应。

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引用次数: 0

A Chromium Catalytic System for the Synthesis of Aryl-Substituted 1,3,5-Triazines and Pyrimidines by Acceptorless Dehydrogenative Coupling 通过无受体脱氢偶联合成芳基取代的 1,3,5-三嗪和嘧啶的铬催化系统

IF 2.8 3区化学 Q2 CHEMISTRY, ORGANIC

European Journal of Organic Chemistry

Pub Date : 2024-10-18 DOI: 10.1002/ejoc.202400993

Baojin Feng, Wantong Yue, Dongyue Wei, Qing Chen, Chuanqi Liu, Xiaoqian Wang, Yilei Wang, Zhihua Peng

A novel and highly efficient methodology for the synthesis of 2,4,6-triaryl-1,3,5-triazines and 2,4,6-trisubstituted pyrimidines from amidines and alcohols has been established. Using the Earth-abundant and air-stable chromium salt catalyst and the phosphine-free ligand, the developed Cr-catalyzed acceptorless dehydrogenative coupling provides 1,3,5-triazines and pyrimidines with high yields and good functional group tolerance. Moreover, the synthetic value of this operationally simple protocol was demonstrated by gram-scale experiment and the synthesis of the linker to construct various supramolecular complexes.

我们建立了一种新颖高效的方法，用于从脒和醇合成 2,4,6-三芳基-1,3,5-三嗪和 2,4,6-三取代嘧啶。利用地球富集且空气稳定的铬盐催化剂和无膦配体，所开发的铬催化无受体脱氢偶联法能以高产率和良好的官能团耐受性制备 1,3,5-三嗪和嘧啶。此外，通过克级实验和合成连接体以构建各种超分子复合物，证明了这一操作简单的方案的合成价值。

引用次数: 0

Gilding the Lily: Studies on the Effects of Successive Loading of Light Energy‐Storing Molecules with Norbornadiene Units 为百合花锦上添花：研究连续添加降冰片二烯单元的光储能分子的影响

IF 2.8 3区化学 Q2 CHEMISTRY, ORGANIC

European Journal of Organic Chemistry

Pub Date : 2024-10-18 DOI: 10.1002/ejoc.202401090

Robin Schulte, Dustin Schade, Thomas Paululat, Heiko Ihmels

The photochromic norbornadiene‐quadricyclane cycle has emerged as a promising basis for molecular solar thermal (MOST) energy storage. In this context, it has been established that multifunctional photoswitches with several norbornadiene units at one central aromatic core have favorable photochemical properties and storage capacities. Nevertheless, a maximum number of three norbornadiene units has been combined in one molecule, so far. In this work, scope and limits of this approach should be further assessed. Thus, exemplary polyfunctionalized derivatives have been synthesized by Suzuki‐Miyaura reactions, and their suitability for MOST applications was investigated. These compounds were converted into the corresponding quadricyclanes by direct UV irradiation (λex = 315 nm) with moderate quantum yields, whereas the reaction is more efficient upon irradiation with λex = 520 nm in the presence of photosensitizers. But these molecules showed low stabilities and short half‐lifes of 1 to 2 days. Moreover, the photochemical reaction is hampered by the close vicinity of photoactive units. Therefore, it appears that in such assemblies, a maximum number of three norbornadiene units is the limit to keep the optimal balance of photochemical properties required for MOST applications.

光致变色降冰片二烯-四环烷循环已成为分子太阳能热（MOST）储能的一个有前途的基础。在这种情况下，已经证实在一个芳香族中心核上含有多个降冰片二烯单元的多功能光开关具有良好的光化学特性和储能能力。不过，迄今为止，在一个分子中最多只能结合三个降冰片二烯单元。在这项工作中，应进一步评估这种方法的范围和局限性。因此，我们通过 Suzuki-Miyaura 反应合成了多官能化衍生物，并研究了它们在 MOST 应用中的适用性。通过紫外线直接照射（λex = 315 纳米），这些化合物转化为相应的四环化合物，量子产率适中，而在光敏剂存在的情况下，用 λex = 520 纳米照射，反应效率更高。但这些分子的稳定性较低，半衰期较短，仅为 1 到 2 天。此外，光化学反应还受到光活性单元邻近的阻碍。因此，在这种组合物中，要保持 MOST 应用所需的光化学特性的最佳平衡，最多只能有三个降冰片二烯单元。

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引用次数: 0

Convenient Synthesis of Dihydrobenzofuran-Fused Spirocyclopentane-1,2-Diindolinone Scaffolds 方便合成二氢苯并呋喃融合螺环戊烷-1,2-二吲哚啉酮支架

IF 2.8 3区化学 Q2 CHEMISTRY, ORGANIC

European Journal of Organic Chemistry

Pub Date : 2024-10-17 DOI: 10.1002/ejoc.202400777

Ting Tang, Ying Han, Chao-Guo Yan, Kun Huang, Jing Sun

A convenient synthetic protocol for diverse functionalized dihydrobenzofuran-fused spirocyclopentane-1,2-diindolin-ones with high diastereoselectivity is developed by base promoted domino annulation reaction of MBH carbonates of isatins and 3-(o-hydroxybenzylidene)indolin-2-ones. The relative configurations of the various polycyclic compounds are clearly elucidated by determination eight single crystal structures.

通过异汀和 3-(邻羟基亚苄基)吲哚啉-2-酮的 MBH 碳酸酯的碱促进多米诺环化反应，开发出一种具有高非对映选择性的多种功能化二氢苯并呋喃融合螺环戊烷-1,2-二吲哚啉-酮的简便合成方案。通过测定八种单晶结构，清楚地阐明了各种多环化合物的相对构型。

引用次数: 0

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