Green Synthesis and Catalysis最新文献

英文中文

Solvent-controlled stereodivergent synthesis of E- and Z-enamines via metal-free formal C(sp2)-H amination of α-substituted styrenes 通过α-取代苯乙烯的无金属C(sp2)- h胺化，溶剂控制立体发散合成E-和z -胺

Green Synthesis and Catalysis

Pub Date : 2024-11-01 Epub Date: 2023-11-14 DOI: 10.1016/j.gresc.2023.11.003

Dangui Wang , Jinbei Yao , Wentao Zhang , Shuyue Zhang , Huaibin Yu , Laihu Peng , Weijun Yao , Zhifeng Dai , Guojiao Wu , Fangrui Zhong

C(sp²)-H amination represents an attractive approach for the synthesis of enamines, which is intrinsically associated with the challenge of controlling of stereochemistry and primarily relying on transition-metal catalysis. Herein, a metal-free C(sp²)-H amination of α-substituted styrenes has been achieved, leading to stereodivergent formation of both E- and Z-enamines in 50 %–97 % yield under mild conditions by using PhI(OAc)₂ as a green oxidant and ortho-phenylenediamines as nitrogen source. Interestingly, the Z/E selectivity can be controlled readily by switching the reaction medium. E-isomers were formed preferentially in THF, whereas n-hexane favored the formation of Z-isomers. Preliminary mechanistic studies suggested that in situ formed ortho-benzoquinone diimides are the key intermediates, and there is a correlation between solvent polarity and stereoselectivity. This study enriches the chemical repertoire of ortho-benzoquinone diimides particularly with respect to sustainable amination.

C(sp2)-H胺化是一种有吸引力的胺合成方法，它与立体化学控制的挑战和主要依赖过渡金属催化有着内在的联系。在温和条件下，以PhI(OAc)2为绿色氧化剂，邻苯二胺为氮源，实现了α-取代苯乙烯的无金属C(sp2)- h胺化反应，生成了E-和z -胺，产率为50% - 97%。有趣的是，通过切换反应介质，可以很容易地控制Z/E选择性。在THF中，e -异构体优先形成，而正己烷则有利于z -异构体的形成。初步的机理研究表明，原位形成的邻苯醌二亚胺是关键的中间体，溶剂极性与立体选择性之间存在相关性。这项研究丰富了对苯醌二亚胺的化学库，特别是在可持续胺化方面。

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引用次数: 0

Transition-metal and base-free ether synthesis via alcohol-participated yne-allylic substitution 醇参与的炔烯取代法合成过渡金属和无碱醚

Green Synthesis and Catalysis

Pub Date : 2024-11-01 Epub Date: 2023-10-21 DOI: 10.1016/j.gresc.2023.10.003

Chao Xu , Yingkun Luo , Shengtong Niu , Fan Gong , Shouang Lan , Benlong Luo , Jinggong Liu , Shuang Yang , Xinqiang Fang

Ethers are among the most important chemicals in organic synthesis, the pharmaceutical industry, agrochemical production, and material science. C–O bond formation via substitution is one of the most widely used strategies for ether formation. However, known methods usually employ transition-metal and bases to facilitate the process. In this work, we describe the base- and transition-metal-free ether formation via alcohol and phenol-participated substitution. The protocol allows access to a large number of ethers with enyne functional moieties, and features mild reaction conditions, high efficiency, and good regio- and stereoselectivities. The reaction could be readily scaled up, and the products could be used in a range of further transformations.

醚是有机合成、制药工业、农用化学品生产和材料科学中最重要的化学品之一。通过取代形成碳氧键是最广泛使用的乙醚形成策略之一。然而，已知的方法通常使用过渡金属和碱基来促进这一过程。在这项工作中，我们描述了通过醇和酚参与取代的无碱和过渡金属醚形成。该方案允许接触到大量具有炔官能团的醚，具有反应条件温和，效率高，区域选择性和立体选择性好的特点。该反应可以很容易地扩大规模，产物可以用于一系列进一步的转化。

引用次数: 0

Electrochemical enabled desaturated β-C(sp3)-H sulfonylation and phosphonylation of cyclic amines 电化学使环胺的去饱和β-C(sp3)-H磺化和膦化

Green Synthesis and Catalysis

Pub Date : 2024-11-01 Epub Date: 2023-11-28 DOI: 10.1016/j.gresc.2023.11.008

Tao Liu , Jie Lin , Fangjun Xia , Zhenhui Xu , Xuying Xia , Wei Qian , Weihui Zhong , Dingguo Song , Fei Ling

Herein, we reported an efficient and straightforward method to realize desaturated β-C(sp³)-H sulfonylation and phosphonylation of cyclic amines driven by electrochemistry using catalytic amounts of CP₂Fe as the redox mediator. This protocol which had good functional group compatibility, provided the desired enaminyl sulfone and enaminyl phosphine oxide products with high chemo- and regio-selectivity under mild conditions. Several mechanistic studies have suggested that cyclic amines underwent multiple single-electron oxidation and deprotonation processes, followed by a capture step involving either a sulfonyl radical or a phosphonyl radical, ultimately leading to the desired products.

本文报道了一种高效、直接的方法，利用催化量的CP2Fe作为氧化还原介质，在电化学驱动下实现环胺的去饱和β-C(sp3)-H磺化和膦化。该工艺具有良好的官能团相容性，在温和的条件下获得了具有高化学选择性和区域选择性的胺基砜和胺基氧化膦产品。一些机制研究表明，环胺经历了多个单电子氧化和去质子化过程，随后是一个涉及磺酰自由基或膦酰自由基的捕获步骤，最终产生所需的产物。

引用次数: 0

Highly enantio-stereoselective Ni-catalyzed reductive cyclization to cyclopentanes with chiral quaternary centres of trisubstituted allylic siloxanes 高对映立体选择性镍催化的三取代烯丙基硅氧烷手性季中心环戊烷还原环化反应

Green Synthesis and Catalysis

Pub Date : 2024-11-01 Epub Date: 2023-09-01 DOI: 10.1016/j.gresc.2023.08.004

Wanjun Chen , Xinlong Yan , Lin Fan , Xu Guo , Jian Yang , Yiming Chen , Shaofang Zhou , Guodu Liu

The construction of chiral quaternary carbon stereocenters is a significant challenge in asymmetric synthesis. Catalytic synthesis of these structures with trisubstituted allylic alcohols is highly important. However, most of the reported methodologies required noble transition-metals. Herein we reported the first highly asymmetric stereoselective synthesis of cyclopentanes bearing chiral quaternary carbon stereocenters of trisubstituted allylic siloxanes by reductive cyclization of all carbon 1,6-alkynones with the non-noble nickel catalysis of Ni(cod)₂ with P-chiral monophosphine ligand (S)-BIDIME. Various multi-substituted functionalized cyclopentanes were obtained in high yields (up to 96%), excellent enantioselectivities (up to >99% ee) and perfect stereoselectivities (>99:1 E/Z). Thirty-two examples were successfully established for this method. Clarified mechanism studies were investigated first time by React-IR and DFT calculations to understand and explain the ligand-control of excellent enantio-stereoselectivity. Gram-scale reaction and control experiments were carried out. A new reaction design was proposed for further application of this type of catalysis.

手性季碳立体中心的构造是不对称合成中的一个重大挑战。用三取代烯丙醇催化合成这些结构是非常重要的。然而，大多数报告的方法都需要贵重的过渡金属。本文报道了在Ni(cod)2和p -手性单膦配体(S)-BIDIME的非贵金属镍催化下，通过1,6-炔酮全碳还原环化，首次合成了具有手性季碳立体中心的三取代烯丙基硅氧烷的高度不对称立体选择性环戊烷。以高收率（96%）、优异的对映选择性（99% ee）和良好的立体选择性（99:1 E/Z）得到了多种多取代功能化环戊烷。该方法成功建立了32个算例。通过反应- ir和DFT计算，首次研究了明确的机理，以了解和解释配体对良好的对映立体选择性的控制。进行了克级反应和对照实验。提出了一种新的反应设计，以进一步应用这种类型的催化剂。

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引用次数: 0

Photoinduced decatungstate-catalyzed direct coupling of cycloalkanes and cyclic aldimines 光诱导十钨酸盐催化环烷和环醛胺的直接偶联

Green Synthesis and Catalysis

Pub Date : 2024-11-01 Epub Date: 2023-10-18 DOI: 10.1016/j.gresc.2023.10.002

Jingjing Wang , Feng Li , Kai Liu , Chong Li , Sheng Cao , Yuxiang Wu , Yongjun Yuan , Fei Teng , Teng Wang , Yao Zhou

We first describe a photoinduced decatungstate-catalyzed direct coupling of cycloalkanes and cyclic aldimines. The desired products were generated in moderate to good yields with wide substrate scope under mild reaction conditions. The mechanistic study revealed a radical process. In addition, the usefulness of the reaction in organic synthesis was proved by the scale-up synthesis as well as the late-stage modification of drug-like molecules.

我们首先描述了光诱导十钨酸盐催化的环烷烃和环醛胺的直接偶联。在温和的反应条件下，以中高收率和宽底物范围生成所需的产物。机械学研究揭示了一个根本性的过程。此外，该反应在有机合成中的有用性被放大合成和后期修饰的类药物分子所证明。

引用次数: 0

Transition metal-free Csp3-Csp3 bond-forming reactions of N-tosylaziridines and gem-diborylalkanes n - tosyziridine和gem-二硼烷的无过渡金属Csp3-Csp3成键反应

Green Synthesis and Catalysis

Pub Date : 2024-11-01 Epub Date: 2023-07-26 DOI: 10.1016/j.gresc.2023.07.004

Pu-Zhang Zi , Quan-Hong Zhao , Zhan-Cai Ma , Xiao-Lin Ren , Xing-Bang Liu , Yi-Wei Qiao , Lin-Wen Wei , Song Liu , Yuan Huang

The incorporation of additional Csp³ atoms into candidate drugs may enhance their pharmacological properties. Nevertheless, it remains challenging to construct desired Csp³-Csp³ bonds efficiently and practically. The present article reports a novel Csp³-Csp³ bond-forming reaction of 2-aryl/alkyl substituted aziridines with gem-diborylalkanes under tranisiton metal free conditions. A wide range of γ-gem-diboronate esters substituted amines can be accessed in good yield and regioselectivity. The results demonstrated that various aziridines could react with gem-diborylalkanes in the presence of LiTMP as the base within 15 min at ambient temperature.

在候选药物中加入额外的Csp3原子可以增强其药理学性质。然而，如何高效、实用地构建理想的Csp3-Csp3键仍然是一个挑战。本文报道了在无过渡金属条件下，2-芳基/烷基取代氮杂环与宝石二硼烷的Csp3-Csp3成键反应。广泛的γ-宝石二硼酸酯取代胺具有良好的收率和区域选择性。结果表明，在常温条件下，以LiTMP为底物存在的情况下，各种氮杂环类化合物均可与宝石二硼烷在15 min内发生反应。

引用次数: 0

Photocatalytic selective 1,4-oxyimination/diamination across C=C and N=N bonds to access structurally diverse N-N-N triazane derivatives 跨 C=C 和 N=N 键的光催化选择性 1,4-氧亚氨基化/二氨基化，获得结构多样的 N-N-N 三氮烷衍生物

Green Synthesis and Catalysis

Pub Date : 2024-08-02 DOI: 10.1016/j.gresc.2024.07.003

Yu-Shi Jiang, Dan-Na Chen, Huan Jiang, Peng-Ju Xia

A highly selective and atom-economical multi-component remote difunctionalization strategy has been successfully developed. This strategy utilizes precise control over the radical properties of bifunctional precursors and the electronic traits of olefins and diazenes to achieve effective radical-mediated 1,4-oxyimination/diamination across C=C and N=N bonds. By capitalizing on compatibility and reactivity tuning, this approach enables the synthesis of complex triazine compounds with an framework, providing a versatile tool for constructing diverse molecular structures. This metal-free method is atom-efficient and adaptable to various substrates, demonstrating remarkable tolerance for a broad range of functional groups.

我们成功开发了一种高选择性和原子经济性的多组分远程双官能化策略。该策略利用对双官能团前体的自由基特性以及烯烃和二苯的电子特性的精确控制，实现了有效的自由基介导的跨 C=C 和 N=N 键的 1,4-氧肟化/二胺化。通过利用兼容性和反应性调整，这种方法能够合成具有框架的复杂三嗪化合物，为构建各种分子结构提供了一种多功能工具。这种无金属方法原子效率高，适用于各种基质，对各种官能团具有显著的耐受性。

引用次数: 0

Rhodium/Ming-Phos-catalyzed asymmetric annulation reaction of silacyclobutanes with terminal alkynes 铑/明磷催化的硅环丁烷与末端炔的不对称环化反应

Green Synthesis and Catalysis

Pub Date : 2024-08-01 Epub Date: 2023-09-07 DOI: 10.1016/j.gresc.2023.09.001

Asymmetric ring-expansion reactions of silacyclobutanes (SCBs) with alkynes have evolved as one of the powerful protocols for the construction of silicon-stereogenic compounds. However, the achievement of highly enantioselective annulation of SCBs with terminal alkynes remains a challenge. Herein, we report a rhodium-catalyzed asymmetric annulation reaction of SCBs with terminal alkynes, which relies on the newly identified chiral sulfinamide phosphine ligand Ming-Phos. This catalytic system exhibits unique effects under mild conditions, leading to the direct synthesis of structurally diverse chiral silacycles in moderate to good yields with high enantioselectivities (up to 95% ee).

硅环丁烷（SCB）与炔烃的不对称扩环反应已发展成为构建硅立体化合物的有力方案之一。然而，实现 SCB 与末端炔烃的高对映选择性环化反应仍然是一项挑战。在此，我们报告了铑催化的 SCB 与末端炔烃的不对称环化反应，该反应依赖于新发现的手性亚磺酰胺膦配体 Ming-Phos。该催化体系在温和的条件下表现出独特的效果，可直接合成结构多样的手性硅环，产率从中等到良好，对映选择性高（高达 95%ee）。

引用次数: 0

N-Doped graphene fiber anchored Pd nanoparticles as a fixed-bed catalyst for continuous-flow reduction of N-containing unsaturated compounds 掺杂 N 的石墨烯纤维锚定钯纳米颗粒作为固定床催化剂用于连续流还原含 N 的不饱和化合物

Green Synthesis and Catalysis

Pub Date : 2024-08-01 Epub Date: 2023-09-09 DOI: 10.1016/j.gresc.2023.08.003

Catalytic fixed-bed is an efficient and facile system for scalable organic synthesis due to its continuous and fast flow operation process. As a key unit in the fixed-bed system, catalytically active packing materials are required to possess some properties, such as high activity, excellent stability, and porous packing structure. Herein, we prepare a fibrous fixed-bed catalyst by anchoring Pd nanoparticles on N-doped graphene fiber (NHG) (Pd/NGF). Due to the porous and loose packing structure, the resultant Pd/NGF catalyst can be easily filled into the continuous-flow reactor to construct a fixed-bed system with low flow resistance. The corresponding catalytic fixed-bed system exhibits a favourable flow rate (8 mL/min) and excellent durability toward reduction reactions of N-containing unsaturated compounds to produce aromatic amines. This work provides a new design concept of fibrous fixed-bed catalysts with dual-active components (i.e., graphene-derived active materials and metal nanoparticles) and catalytic organic synthesis in a continuous-flow process.

催化固定床因其连续、快速的流动操作过程，是一种高效、简便的可扩展有机合成系统。作为固定床系统中的关键单元，催化活性填料需要具备高活性、高稳定性和多孔填料结构等特性。在此，我们将钯纳米颗粒锚定在掺杂 N 的石墨烯纤维（NHG）（Pd/NGF）上，制备了一种纤维状固定床催化剂。由于Pd/NGF催化剂具有多孔和松散的堆积结构，因此可以很容易地填充到连续流反应器中，从而构建一个低流动阻力的固定床系统。相应的催化固定床系统对含 N 的不饱和化合物的还原反应生成芳香胺具有良好的流速（8 mL/min）和出色的耐久性。这项工作为具有双活性成分（即石墨烯衍生活性材料和金属纳米颗粒）的纤维状固定床催化剂和连续流工艺中的催化有机合成提供了一种新的设计理念。

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引用次数: 0

Iridium-Catalyzed asymmetric reduction of α,β-Unsaturated nitriles with water 铱催化的α、β-不饱和腈与水的不对称还原反应

Green Synthesis and Catalysis

Pub Date : 2024-08-01 Epub Date: 2023-07-22 DOI: 10.1016/j.gresc.2023.07.002

The nitrile compounds are present in a variety of biologically active natural products and pharmaceuticals, and the nitrile groups are versatile synthetic intermediates to other functionalized compounds. Herein, the asymmetric reduction of α, β-unsaturated nitriles with water as a hydrogen source is reported. The reaction is catalyzed by the complex of [Ir(COD)Cl]₂ and (R_a, S)-Ph-Bn-SiPhox, and allows the preparation of useful enantioenriched chiral 3,3-disubstituted propionitriles with high optical purities in mild conditions.

腈类化合物存在于多种具有生物活性的天然产物和药物中，腈基是合成其他功能化化合物的多功能中间体。本文报告了以水为氢源对 α、β-不饱和腈进行不对称还原的过程。该反应由[Ir(COD)Cl]2 和 (Ra, S)-Ph-Bn-SiPhox 复合物催化，可在温和的条件下制备出光学纯度高的对映体丰富的手性 3,3-二取代丙腈。

引用次数: 0

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Green Synthesis and Catalysis

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