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Aliphatic Olefin Epoxidation with Hydrogen Peroxide Catalyzed by an Integrated Mn/TS-1/N System Mn/TS-1/N 集成系统催化的脂肪族烯烃与过氧化氢的环氧化反应
IF 2 4区 化学 Q3 CHEMISTRY, ORGANIC Pub Date : 2024-05-28 DOI: 10.1055/s-0043-1775366
Shanxiu Yang, Yuyu Liu, Zhang Zhang, Bo Qian

Propylene liquid-phase epoxidation with 50–75% H2O2 is an important process for the industrial production of propylene oxide (PO). To realize a propylene epoxidation process that proceeds with low hydrogen peroxide concentration, we developed an integrated Mn/TS-1/N catalytic system via in-situ reaction of Mn/TS-1 with an N-donor ligand, affording the PO product in excellent yield with only 30 wt% H2O2. Other long-chain aliphatic epoxides were also readily synthesized by this catalytic epoxidation system. Moreover, in addition to the standard micro-pressure reactor, a continuous-flow microreactor was developed that executed the hydrogen peroxide propylene oxide (HPPO) process with excellent efficiency for 1300 hours. This innovative Mn/TS-1/N catalyzed epoxidation represents a promising direction for advancing HPPO industrial processes, offering improved efficiency while minimizing the reliance on high concentrations of H2O2.

丙烯液相环氧化(50-75% H2O2)是环氧丙烷(PO)工业生产的重要工艺。为了实现低过氧化氢浓度下的丙烯环氧化工艺,我们开发了一种集成的 Mn/TS-1/N 催化系统,通过 Mn/TS-1 与 N-供体配体的原位反应,只需 30 wt% 的 H2O2 即可获得产率极高的环氧丙烷产品。其他长链脂肪族环氧化物也很容易通过这种催化环氧化体系合成。此外,除了标准的微压反应器外,还开发了一种连续流微反应器,可在 1300 小时内高效执行过氧化氢环氧丙烷(HPPO)工艺。这种创新的 Mn/TS-1/N 催化环氧化技术代表了推进 HPPO 工业流程的一个有前途的方向,它在提高效率的同时,最大限度地减少了对高浓度 H2O2 的依赖。
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引用次数: 0
Metal-Free Synthesis of C-3-Alkoxycarbonylated 2H-Indazoles Using Alkyl Carbazates 使用烷基咔嗪酸盐无金属合成 C-3-烷氧基羰基 2H-Indazoles
IF 2 4区 化学 Q3 CHEMISTRY, ORGANIC Pub Date : 2024-05-16 DOI: 10.1055/a-2316-5066
Dipti Lai, Suvam Bhattacharjee, Sumit Ghosh, Subrata Sinha, Alakananda Hajra

A simple, efficient, and environmentally benign method for the direct C-3-alkoxycarbonylation of 2H-indazoles using alkyl carbazates has been developed under metal-free conditions at room temperature. This current protocol represents a facile access to C-3-carboxylic ester derived 2H-indazoles with wide functional group tolerance in good to excellent yields. The mechanistic studies suggest that the reaction proceeds through a radical pathway.

在室温无金属条件下,利用烷基咔嗪酸盐直接对 2H-indazoles 进行 C-3-alkoxycarbonylation 的简单、高效和环保方法已经开发出来。目前的这一方法可以方便地获得 C-3-羧酸酯衍生的 2H-吲唑,且具有广泛的官能团耐受性,收率良好甚至极佳。机理研究表明,反应是通过自由基途径进行的。
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引用次数: 0
Silver-Mediated Homocoupling of Arylboronic Acids 银介导的芳硼酸同偶联反应
IF 2 4区 化学 Q3 CHEMISTRY, ORGANIC Pub Date : 2024-05-14 DOI: 10.1055/a-2315-8369
Tomoya Sakaguchi, Kyuta Fukuoka, Takuya Matsuki, Misa Kawase, Aya Tazawa, Yasuhiro Uozumi, Yoshimasa Matsumura, Osamu Shimomura, Atsushi Ohtaka

Here we describe a homocoupling reaction of arylboronic acid facilitated by silver carbonate, which proceeds smoothly in MeOH even at ambient temperature. The reaction exhibits broad functional group compatibility, affording a variety of symmetrical biaryls in satisfactory yields. Silver nanoparticles formed in situ serve as an accelerator in this process. Moreover, initial mechanistic investigations suggest that this transformation may occur via a radical mechanism.

在此,我们介绍了一种由碳酸银促进的芳基硼酸均偶联反应,该反应即使在环境温度下也能在 MeOH 中顺利进行。该反应具有广泛的官能团兼容性,能以令人满意的产率获得各种对称双芳基。在这一过程中,原位形成的银纳米粒子起到了加速器的作用。此外,初步的机理研究表明,这种转化可能是通过自由基机理发生的。
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引用次数: 0
One-Pot Expeditious Synthesis of Pyrazoloindolones via Base-Promoted Electrocyclization, C–N Coupling and Intramolecular Oxidative Cyclization 通过碱促进的电环化、C-N 偶联和分子内氧化环化快速合成吡唑吲哚酮类化合物
IF 2 4区 化学 Q3 CHEMISTRY, ORGANIC Pub Date : 2024-05-14 DOI: 10.1055/a-2316-5200
Harshita Singh Korawat, Manoj Kumar Saini, Karmdeo Prajapati, Maya Shankar Singh, Ashok Kumar Basak

Pyrazoloindolones are synthesized from N-tosylhydrazones in a one-pot multistep process which include base-promoted (i) electrocyclization reaction of N-tosylhydrazones derived from α,β-unsaturated aldehydes, (ii) aromatic nucleophilic substitution, and (iii) a domino cyclization–oxidation process under aerobic conditions.

吡唑吲哚酮是由 N-对甲苯磺酸肼通过单锅多步工艺合成的,该工艺包括碱促进的 (i) α、β-不饱和醛类衍生的 N-对甲苯磺酸肼的电环化反应,(ii) 芳香族亲核取代,以及 (iii) 有氧条件下的多米诺环化-氧化过程。
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引用次数: 0
Bismuth Triflate Catalyzed Intermolecular Cyclization of Thiophenols with Allylic Alcohols 三氟化铋催化噻吩醇与烯丙基醇的分子间环化反应
IF 2 4区 化学 Q3 CHEMISTRY, ORGANIC Pub Date : 2024-05-06 DOI: 10.1055/a-2312-0631
Maki Minakawa, Taichi Inaba, Shoki Oikawa

The catalytic intermolecular cyclization of thiophenols with allylic alcohols in the presence of bismuth triflate afforded the corresponding thiochromane derivatives in a one-pot reaction. The Bi(OTf)3-catalyzed reaction was also applied to the intermolecular cyclization of diaryl disulfides with 3-methylbut-2-en-1-ol to produce the corresponding thiochromanes.

在三酸铋存在下,噻吩酚与烯丙基醇的分子间环化催化反应可在一锅反应中生成相应的硫代苯并吡喃衍生物。Bi(OTf)3 催化的反应还应用于二芳基二硫化物与 3-甲基丁-2-烯-1-醇的分子间环化反应,生成相应的硫代色烷。
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引用次数: 0
A Convergent Approach to the Forskolin Skeleton 福斯科林骨架的聚合方法
IF 2 4区 化学 Q3 CHEMISTRY, ORGANIC Pub Date : 2024-05-06 DOI: 10.1055/s-0043-1774864
Fortune O. Ononiwu, Bo Wang, Nancy I. Totah

A convergent approach to the forskolin skeleton is described. Assembly of a simplified tricyclic framework is achieved in a single step via the dihydropyrone Diels–Alder reaction. Selective manipulation of the resulting cycloadduct, in conjunction with an unusual equilibration of the C8 stereocenter, provides access to scaffolds that differ in relative stereochemistry at both the A/B and B/C ring junctions.

本研究介绍了一种研究福斯克林骨架的聚合方法。通过二氢吡喃酮 Diels-Alder 反应,只需一步就能组装出简化的三环框架。选择性地操纵所产生的环加载产物,再加上 C8 立体中心的不寻常平衡,就可以获得在 A/B 和 B/C 环连接处具有不同相对立体化学性质的支架。
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引用次数: 0
N-Alkyl-1,2,4-triazole–Borane Complexes as High-Density Hypergolic Materials 作为高密度超醇材料的 N-烷基-1,2,4-三唑-硼烷络合物
IF 2 4区 化学 Q3 CHEMISTRY, ORGANIC Pub Date : 2024-05-06 DOI: 10.1055/a-2310-0707
Hongfu Jia, Wenqi Ma, Jinjie Chang, Chunlin He

Hydrazine and its derivatives have served as a conventional bipropellant fuel for several decades. However, their extremely acute toxicity and carcinogenicity, high volatility, and environmental impact have attracted significant attention. In order to synthesize green bipropellant fuels with high density, high specific impulse, and good thermal stability, three novel N-alkyl-1,2,4-triazole–borane complexes were successfully synthesized by reacting alkylated 1,2,4-triazole coordinated with sodium borohydride in the presence of ammonium sulfate. During the droplet test with white fuming nitric acid, there was a relatively short ignition delay time of 98 ms. Additionally, these hypergolic fuels possessed a high density exceeding 1.10 g cm–3, and the specific impulse is ranging from 187 to 199 s, and the highest decomposition temperature reaches 153.4 °C. These results demonstrate their great potential as hypergolic fuels or hypergolic ionic liquid additives in the field of hypergolic materials.

几十年来,肼及其衍生物一直是传统的双推进剂燃料。然而,它们的剧毒性和致癌性、高挥发性以及对环境的影响引起了人们的极大关注。为了合成具有高密度、高比冲和良好热稳定性的绿色双推进剂燃料,研究人员通过在硫酸铵存在下使烷基化的 1,2,4 三唑与硼氢化钠反应,成功合成了三种新型 N-烷基-1,2,4-三唑-硼烷复合物。在用白色发烟硝酸进行液滴测试时,点火延迟时间相对较短,仅为 98 毫秒。此外,这些双酚燃料的密度超过 1.10 g cm-3,比冲为 187 至 199 s,最高分解温度达到 153.4 ℃。这些结果证明了它们作为超醇燃料或超醇离子液体添加剂在超醇材料领域的巨大潜力。
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引用次数: 0
Ligand-Promoted Palladium-Catalyzed β-C(sp3)–H Arylation of Ketones Using Acetohydrazide as a Transient Directing Group 配体促进的钯催化β-C(sp3)-H 乙酮芳基化反应(以乙酰基酰肼作为瞬时指导基团
IF 2 4区 化学 Q3 CHEMISTRY, ORGANIC Pub Date : 2024-04-29 DOI: 10.1055/a-2310-0880
Kai Jia, Junjie Wang, Xuan Wang, Chao Jiang

A palladium-catalyzed β-C(sp3)–H arylation of aliphatic ketones by using acetohydrazide as a transient directing group has been developed. The reaction proceeds through a less-favored [5,5]-bicyclic palladacycle intermediate and is promoted by a pyridine ligand.

通过使用乙酰肼作为瞬时指导基团,开发了一种钯催化的脂肪族酮的 β-C(sp3)-H 芳基化反应。该反应通过一个不太有利的[5,5]-双环帕拉代环中间体进行,并由吡啶配体促进。
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引用次数: 0
Highly Efficient and Practical Oxidative Bromination of Electron-Rich Arenes Using S-Methyl Methanethiosulfonate as the Oxidant 使用 S-甲基甲硫代磺酸酯作为氧化剂对富电子烯进行高效实用的氧化溴化反应
IF 2 4区 化学 Q3 CHEMISTRY, ORGANIC Pub Date : 2024-04-26 DOI: 10.1055/s-0043-1763752
Shaolong Wang, Yong Zhou, Jianbo Wang, Ruolan Li, Chaoqun Huang, Huailin Pang, Xun Li

An efficient and practical method for the bromination of electron-rich arenes and heteroarenes was developed by using S-methyl methanethiosulfonate as the oxidant. All the bromine atoms were basically transferred to the brominated products, demonstrating the exceptional atom economy and practicality of the proposed protocol. The method reduces the amount of bromine required for this reaction system and obtains products in moderate to good yields.

以 S-甲基甲硫代磺酸酯为氧化剂,开发了一种高效实用的溴化富含电子的烯烃和杂烯烃的方法。所有的溴原子基本上都转移到了溴化产物中,这表明所提出的方案具有出色的原子经济性和实用性。该方法减少了该反应体系所需的溴用量,并能以中等至良好的产率获得产物。
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引用次数: 0
AgSCF3 Radical Addition Based on an Oxidant-Free α,β-Amide (Trifluoromethyl)sulfanylation Reaction 基于无氧化剂 α、β-酰胺(三氟甲基)硫酰化反应的 AgSCF3 自由基加成反应
IF 2 4区 化学 Q3 CHEMISTRY, ORGANIC Pub Date : 2024-04-18 DOI: 10.1055/s-0043-1763759
Zhi-Bo Li, Jin Zhang, Yi-Ran Shi, Hong Li, Min-Ge Yang, Wen-Qing Zhu, Qiang-Wei Fan, Yang Li

(Trifluoromethyl)sulfanylamides are an important class of organic compounds that are common among natural products and drug molecules. Here, we report a (trifluoromethyl)sulfanylation reaction using silver(I) (trifluoromethyl)sulfide as a free-radical (trifluoromethyl)sulfanylation reagent for β-amide compounds. This reaction does not require stoichiometric oxidants or additional transition-metal catalysts, and can be achieved by adding common organic acids. This method has excellent applicability and can accommodate several functional groups, including ester groups, acyl groups, and even bromo or iodo groups. Heterocyclic α,β-amides can also be readily converted into the corresponding products. This reaction also provides a new method for the synthesis of deuterated (trifluoromethyl)sulfanylamides.

(三氟甲基)硫酰胺是一类重要的有机化合物,常见于天然产物和药物分子中。在此,我们报告了一种使用银(I)(三氟甲基)硫化物作为自由基(三氟甲基)硫酰化试剂对 β-酰胺化合物进行(三氟甲基)硫酰化反应的方法。该反应不需要化学计量氧化剂或额外的过渡金属催化剂,只需加入常见的有机酸即可实现。这种方法具有极佳的适用性,可容纳多种官能团,包括酯基、酰基、甚至溴基或碘基等。杂环 α、β-酰胺也很容易转化为相应的产物。该反应还为合成氚代(三氟甲基)硫酰胺提供了一种新方法。
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