Green Synthesis and Catalysis最新文献

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Development of a more efficient catalyst for the redox-neutral organocatalytic mitsunobu reaction by DFT-guided catalyst design 采用dft导向设计一种更高效的氧化还原-中性有机催化mitsunobu反应催化剂

Green Synthesis and Catalysis

Pub Date : 2024-11-01 DOI: 10.1016/j.gresc.2023.11.002

Dingguo Song , Changjun Zhang , Yuqi Cheng , Linlin Chen, Jie Lin, Changdi Zheng, Ting Liu, Yuxin Ding, Fei Ling, Weihui Zhong

The study of a Mitsunobu reaction is an important topic. Denton and co-workers first reported a novel (2-hydroxybenzyl)diphenylphosphine oxide for realizing the catalytic Mitsunobu reaction via a five-membered phosphonium species. However, it is still worth investigating how to improve catalysts with higher efficiency. Guided by computational and experimental studies, we designed a new type of biphenyl-based phosphine oxide that would form a six-membered phosphonium species as a key intermediate to trigger the catalytic Mitsunobu reaction with a lower barrier of the rate-determining step (30.3 kcal/mol). DFT calculations revealed that only trans dehydration was participated in our catalytic progress and a strong π-π interaction and small spatial constraint of TS-V were crucial for high behavior. This readily accessible, highly stable, easily recyclable and efficient catalyst would boost the catalytic Mitsunobu reaction.

光信反应的研究是一个重要的课题。Denton及其同事首次报道了一种新的（2-羟基苄基）二苯基氧化膦通过五元磷实现催化Mitsunobu反应。然而，如何提高催化剂的效率仍值得进一步研究。在计算和实验研究的指导下，我们设计了一种新型的基于联苯的氧化膦，它可以形成六元磷，作为催化Mitsunobu反应的关键中间体，具有较低的定速步垒（30.3 kcal/mol）。DFT计算表明，催化过程只涉及反式脱水，强π-π相互作用和TS-V的小空间约束是高行为的关键。这种易于获取、高度稳定、易于回收和高效的催化剂将促进催化光信反应。

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引用次数: 0

Pictet-spengler/transamination cascade reaction of indoles for modular synthesis of marinoquinoline analogues 喹啉类似物模块化合成中吲哚的Pictet-spengler/转氨化级联反应

Green Synthesis and Catalysis

Pub Date : 2024-11-01 DOI: 10.1016/j.gresc.2023.09.002

Jinjin Chen , Pingyu Jiang , Xinping Liu , Huawen Huang , Guojiang Mao , Guo-Jun Deng

The Pictet-Spengler/transamination cascade reaction enables modular synthesis of marinoquinoline analogues through three-component indole ring-expansion/cyclization in the manner of novel N1–C2 cleavage of indoles. This metal-free protocol exhibits very broad functional group tolerance with up to quantitative yields. Preliminary studies on the antitumor activity of the resultant marinoquinoline analogues reveal that the indolyl-attached pyrrolo[2,3-c]quinoline product (5d) shows great potential (IC₅₀ of 0.32 μg/mL to HeLa cells) as a promising anticancer agent in clinic.

picet - spengler /转氨化级联反应以新颖的吲哚N1-C2裂解方式，通过三组分吲哚扩环/环化，模块化合成了氨基喹啉类似物。这种无金属方案具有非常广泛的官能团耐受性和定量产量。对所得的喹啉类似物抗肿瘤活性的初步研究表明，吲哚偶联吡咯[2,3-c]喹啉产物（5d）对HeLa细胞的IC50为0.32 μg/mL，具有广阔的临床应用前景。

引用次数: 0

Recent advances in (4 + 3) cycloaddition of allenes 烯类化合物(4 + 3)环加成的研究进展

Green Synthesis and Catalysis

Pub Date : 2024-11-01 DOI: 10.1016/j.gresc.2023.11.010

Yanyan Que , Wenli Lei , Yin Fang , Shuzhong He , Yang Chen

Allenes are a class of unsaturated compounds containing a propadiene structural moiety, exhibiting essential physiological, pharmacological, and various reactivities. Their (4 + 3) cycloaddition reaction has become an effective method for synthesizing seven-membered rings, especially for heterocycles. This method has been continuously improved and developed. Herein, we review the (4 + 3) cycloaddition of allenes, focusing on the developed methodologies and the outlook in this field from 2013 to 2023.

烯类化合物是一类含有丙二烯结构的不饱和化合物，具有重要的生理、药理和各种反应活性。他们的(4 + 3)环加成反应已成为合成七元环特别是杂环的有效方法。这种方法得到了不断的改进和发展。本文对(4 + 3)烯的环加成进行了综述，重点介绍了2013 - 2023年这一领域的研究进展和展望。

引用次数: 0

Carbonylative transformation of aryl halides and strong bonds via cheap metal catalysts and sustainable technologies 通过廉价金属催化剂和可持续技术实现芳基卤化物和强键的羰基转化

Green Synthesis and Catalysis

Pub Date : 2024-11-01 DOI: 10.1016/j.gresc.2024.04.008

Maolin Yang , Yukun Liu , Xin Qi , Yanhua Zhao , Xiao-Feng Wu

The development of catalytic carbonylation reactions has increased considerably. Although many reviews/chapters/books on carbonylation reactions have been published, summaries on cheap metal-catalyzed catalytic carbonylation reactions of aryl halides and other chemical bonds with high dissociation energy C–Y (Y = O, N, H) are still very rare. Focusing on green and sustainable chemistry, this review summarizes and discusses the achievements on carbonylative transformations of aryl halides (C(sp²)–X) and strong bonds C–Y (Y = O, N, H) based on non-expensive metal catalysts (Co, Mn, Mo, Ni, Fe, Cu), photochemical and electrochemical systems developed in recent decades.

催化羰基化反应的发展已大大增加。虽然已经发表了很多关于羰基化反应的综述/章节/书籍，但关于廉价金属催化芳基卤化物催化羰基化反应和其他具有高离解能的化学键C-Y （Y = O， N， H）的综述仍然很少。以绿色化学和可持续化学为重点，综述和讨论了近几十年来基于非昂贵金属催化剂（Co, Mn, Mo, Ni, Fe, Cu）和光化学和电化学体系的芳基卤化物（C(sp2) -X）和强键C - Y （Y = O， N， H）羰基化转化的研究进展。

引用次数: 0

Visible-light induced photocatalyst-free difluoromethylation of quinoxalinones with difluorosulfones 可见光诱导的无光催化剂喹啉酮与二氟砜的二氟甲基化

Green Synthesis and Catalysis

Pub Date : 2024-11-01 DOI: 10.1016/j.gresc.2023.08.002

Linlin Shi , Tiantian Li , Wenjing Zhang , Weinan Hu , Xinju Zhu , Yixin Lu , Guang-Jian Mei

Visible-light induced direct C–H difluoromethylation of quinoxalinones with 2-((difluoromethyl)sulfonyl)benzo[d]thiazole has been developed for the first time. A broad range of quinoxalinones were well tolerated and reacted with difluorosulfone smoothly to give the corresponding products in moderate to good yields. Notably, no external photocatalyst or oxidant was required, which provides a practical and green protocol to access difluoromethylated quinoxalinones. Finally, the control experiments demonstrated a radical mechanism, and the density functional theory (DFT) calculations indicated the radicals were generated through the formation of an electron donor−acceptor (EDA) complex.

本文首次报道了喹啉酮类化合物与2-（（二氟甲基）磺酰）苯并[d]噻唑在可见光诱导下的直接C-H二氟甲基化反应。多种喹诺沙林酮具有良好的耐受性，与二氟砜反应平稳，产率中等至较高。值得注意的是，不需要外部光催化剂或氧化剂，这为获取二氟甲基化喹诺沙林酮提供了一种实用和绿色的方案。最后，对照实验证明了自由基机制，密度泛函理论（DFT）计算表明自由基是通过电子供体-受体（EDA）复合物的形成而产生的。

引用次数: 0

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 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

Visible-light-induced radical-cascade alkylation/cyclization of N-methacryloyl-2-phenylbenzimidazole: Access to benzoimidazo[2,1-a]isoquinolin-6(5H)-ones 可见光诱导n-甲基丙烯酰-2-苯基苯并咪唑的自由基级联烷基化/环化：苯并咪唑[2,1-a]异喹啉-6(5H)-酮的制备

Green Synthesis and Catalysis

Pub Date : 2024-11-01 DOI: 10.1016/j.gresc.2023.10.001

Yanhong Wang , Xinlei Zhou , Tao Zhang , Xinxin Ren , Wei Xu , Bin Wang , Weiwei Jin , Yu Xia , Chenjiang Liu , Yonghong Zhang

A metal-free visible-light-induced synthesis of aza-polycyclic aromatic hydrocarbons via cascade alkylation/cyclization of N-methacryloyl-2-phenylbenzimidazole was developed. The reaction was carried out with inactive alkanes and cyclic ethers as alkylation reagents, and phenanthrenequinone (PQ) as a direct hydrogen-atom transfer (HAT) photocatalyst. The desired products were obtained in moderate to good yields at room temperature under air.

研究了n -甲基丙烯酰-2-苯基苯并咪唑级联烷基化/环化在无金属可见光诱导下合成氮杂多环芳烃的方法。以非活性烷烃和环醚为烷基化试剂，邻苯醌（PQ）为直接氢原子转移（HAT）光催化剂进行反应。在室温空气条件下，以中等至良好的产率获得了所需的产品。

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 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 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

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 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

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Green Synthesis and Catalysis

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