Green Synthesis and Catalysis最新文献

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Synthesis of naphtho[1,2-b]furan-2-carbaldehydes and naphtho[2,1-b]furan-2-carbaldehydes via electrocatalytic 3,3-rearrangement/cyclization of propargylic aryl ethers under mild conditions 在温和条件下通过电催化丙炔基芳基醚的 3,3-重排/环化合成萘并[1,2-b]呋喃-2-羰基醛和萘并[2,1-b]呋喃-2-羰基醛

Green Synthesis and Catalysis

Pub Date : 2024-06-01 DOI: 10.1016/j.gresc.2024.05.008

Kaili Cen, Mixia Ouyang, Guojun He, Zhouting Zeng, Qiaolin Wang, Xin Yu, Feng Zhao, Jinhui Cai

引用次数: 0

Stereoselective oxidative C3-N bond dehydrogenation and aromatization of 1-carboxyl substituted tetrahydroisoquinolines employing pipecolate oxidase 利用哌啶醇氧化酶对 1-羧基取代的四氢异喹啉进行立体选择性 C3-N 键氧化脱氢和芳香化反应

Green Synthesis and Catalysis

Pub Date : 2024-06-01 DOI: 10.1016/j.gresc.2024.06.001

Shuyun Ju, Xiaoshu Zhou, Huanhuan Jin, Yang Yang, Lirong Yang, Jianping Wu

引用次数: 0

Photocatalyzed chemodivergent aerobic oxidation of naturally occurring Viridicatin and derivatives 光催化化学发散有氧氧化天然维甲酸及其衍生物

Green Synthesis and Catalysis

Pub Date : 2024-06-01 DOI: 10.1016/j.gresc.2024.05.010

Yingxian Li, Hui Wang, Xuemin Jia, Bing Guo, Yuanyong Yang, Lei Tang, Zhiyong Jiang

引用次数: 0

Modulating regioselectivity of CYP107J3-catalyzed isophorone hydroxylation by disrupting the hydrophobic balance of the substrate binding pocket 通过破坏底物结合袋的疏水平衡调节 CYP107J3 催化的异佛尔酮羟基化的区域选择性

Green Synthesis and Catalysis

Pub Date : 2024-05-31 DOI: 10.1016/j.gresc.2024.05.007

Meng Dai, Xiaojuan Yu, Xiaogang Peng, Zhiyong Guo, Huili Yu, Aitao Li

4-Hydroxyisophorone (4HIP) is an oxygenated intermediate derived from isophorone, serving as an important flavor and fragrance and chiral synthon of pharmaceutical drugs. In this study, a newly identified P450CYP107J3 from was found to prefer 4-hydroxylation of isophorone (80% regioselectivity) with 4HIP as the predominant product (59% product proportion). Bioinformatic analyses, including homologous modelling and molecular docking, reveal that four potential “hotspot” residues (L98, T300, M401 and V296) located on both sides of the substrate in the active pocket may control regioselectivity. By introducing polar residues to these hotspots to disrupt the hydrophobic balance, significant improvement in C4-regioselectivity was achieved by variants of L98, T300, and M401, with the most effective L98N exhibiting a notable enhancement of 93% C4-regioselectivity including 81% of 4HIP. Following, the double mutant L98N-M401F further improved both C4-regioselectivity (97%) and the proportion of 4HIP (86%). Remarkably, variant V296T essentially shifted regioselectivity from 4HIP to 6-hydroxyisophorone (6HIP) with an 80% preference for the latter, indicating the crucial role of V296 in controlling regioselectivity. Subsequently, the mechanism of regioselectivity of isophorone hydroxylation catalyzed by CYP107J3 was revealed by computational analysis. Furthermore, we demonstrated the generality of conserved hotspots L98 and V296 in mediating regioselectivity control in the CYP107J family members like CYP107J1 and CYP107J5. Overall, our study not only expands the biocatalytic toolbox for producing 4HIP and the -hydroxy ketone 6HIP but also provides efficient engineering strategy and knowledge for the regioselectivity control of P450s in potential applications.

4-羟基异佛尔酮（4HIP）是异佛尔酮衍生的含氧中间体，是一种重要的香精香料和药物手性合成物。本研究发现，新发现的 P450CYP107J3 偏好异佛尔酮的 4- 羟基化（80% 的区域选择性），4HIP 是主要产物（产物比例为 59%）。包括同源建模和分子对接在内的生物信息学分析表明，位于活性袋底物两侧的四个潜在 "热点 "残基（L98、T300、M401 和 V296）可能控制着区域选择性。通过在这些热点残基上引入极性残基以破坏疏水平衡，L98、T300 和 M401 的变体显著提高了 C4 区域选择性，其中最有效的 L98N 显著提高了 93% 的 C4 区域选择性，包括 81% 的 4HIP。随后，双突变体 L98N-M401F 进一步提高了 C4regi 选择性（97%）和 4HIP 的比例（86%）。值得注意的是，变体 V296T 从根本上将区域选择性从 4HIP 转移到了 6-羟基异佛尔酮（6HIP），对后者的偏好达到了 80%，这表明 V296 在控制区域选择性方面起着至关重要的作用。随后，我们通过计算分析揭示了 CYP107J3 催化异佛尔酮羟基化的区域选择性机制。此外，我们还证明了保守热点 L98 和 V296 在 CYP107J 家族成员（如 CYP107J1 和 CYP107J5）中介导区域选择性控制的普遍性。总之，我们的研究不仅扩展了生产 4HIP 和-羟基酮 6HIP 的生物催化工具箱，而且为潜在应用中 P450s 的区域选择性控制提供了有效的工程策略和知识。

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引用次数: 0

Asymmetric synthesis of allylic sulfonamides with axially and central chirality via palladium-catalyzed of atroposelective N-allylic alkylation 通过钯催化的反选择性 N-烯丙基烷基化不对称合成具有轴向和中心手性的烯丙基磺酰胺类化合物

Green Synthesis and Catalysis

Pub Date : 2024-05-25 DOI: 10.1016/j.gresc.2024.05.006

Dayuan Wang, Jiayi Zong, Bowen Wang, Longwu Sun, Xiao Xiao, Huri Piao, Miaolin Ke, Fener Chen

引用次数: 0

Catalyst-free electrochemical dearomatization of pyridine derivatives 吡啶衍生物的无催化剂电化学脱芳烃反应

Green Synthesis and Catalysis

Pub Date : 2024-05-01 DOI: 10.1016/j.gresc.2022.06.006

Kui Wang , Yingjun Tian , Baoying Li , Ling Wang , Wei Gao , Xiaofei Jia , Ruiming Wang , Yanping Zhu , Jianbin Chen

We demonstrated herein an electrochemical dearomatizative alkylation of Katritzky salts, wherein Katritzky salts were harnessed as both radical acceptors and donors. A wide range of privileged dihydropyridine scaffolds was constructed with good to excellent yields. Cyclic voltammetry (CV) and electron paramagnetic resonance (EPR) results confirmed the key intermediates-dihydropyridine radicals and gram-scale reaction highlighted the practical and sustainable feature of the newly developed protocol.

我们在此展示了卡氏盐的电化学脱芳烃烷基化反应，其中卡氏盐既可用作自由基受体，也可用作自由基供体。研究人员以良好至极佳的产率构建了多种特效二氢吡啶支架。循环伏安法（CV）和电子顺磁共振（EPR）结果证实了二氢吡啶自由基的关键中间体，而克级反应则突出了新开发方案的实用性和可持续性。

引用次数: 0

Cascade reaction of 3-formylchromones: Highly selective synthesis of 4-oxo-3-(1H-pyrrol-3-yl)-4H-chromenes 3- 甲酰基色素的级联反应：高选择性合成 4-氧代-3-(1H-吡咯-3-基)-4H-色烯

Green Synthesis and Catalysis

Pub Date : 2024-05-01 DOI: 10.1016/j.gresc.2022.10.003

Ying Lv, Li Chen, Xinghan Yun, Kun Li, Shengjiao Yan

A novel method for the preparation of highly functionalized 4-oxo-3-(1H-pyrrol-3-yl)-4H-chromenes (OPCMs) from 3-formylchromones and α-isocyanoacetates via an unprecedented three-component [1 + 1 + 3] cycloaddition reaction in one pot was developed. The three-component cascade reaction was enabled by refluxing a mixture of the substrates in 1,4-dioxane in the presence of Ag₂CO₃ as a Lewis acid promoter. As a result, a series of functionalized pyrroles (OPCMs, 3), was prepared regioselectively and in high yields (80%–88%) through the formation of three bonds. This protocol can be used in the synthesis of OPCMs rather than through conventional, multi-step reactions and is suitable for both combinatorial and parallel syntheses of pyrroles.

本研究开发了一种新方法，以 3-甲酰基色素和 α-异氰基乙酸酯为原料，通过前所未有的三组分 [1 + 1 + 3] 环加成反应，在一锅内制备高度官能化的 4-氧代-3-(1H-吡咯-3-基)-4H-苯并吡喃（OPCMs）。在 Ag2CO3 作为路易斯酸促进剂存在的情况下，通过回流 1,4- 二氧六环中的底物混合物，实现了三组分级联反应。结果，通过形成三个键，一系列官能化吡咯（OPCMs, 3）以高产率（80%-88%）被区域选择性地制备出来。该方案可用于合成 OPCMs，而不是通过传统的多步反应，并且适用于吡咯的组合合成和平行合成。

引用次数: 0

Chemoselective synthesis of α-carboline derivatives via hypervalent iodine-catalyzed [3+3] annulation under metal-free conditions 在无金属条件下通过高价碘催化 [3+3] 环化化学选择性合成 α-咔啉衍生物

Green Synthesis and Catalysis

Pub Date : 2024-05-01 DOI: 10.1016/j.gresc.2023.01.002

Shuowen Wang , Rong Li , Shanping Chen , Guojiang Mao , Wen Shao , Guo-Jun Deng

A strategy for the synthesis of α-carboline derivatives from indole-3-carboxaldehydes and 3-aminocyclohex-2-enones under metal-free conditions has been developed. The combination use of phenyliodine (III) diacetate (PIDA) and benzoic acid could significantly facilitate the corresponding [3 + 3] annulation process. This newly developed strategy featured unextraordinary chemoselectivity, good functional group tolerance and the preservation of the carbonyl group of the ketone substrates, which offers the possibility for further transformation of the products.

我们开发了一种在无金属条件下从吲哚-3-甲醛和 3-氨基环己-2-烯酮合成 α-咔啉衍生物的策略。苯碘 (III) 二乙酸酯 (PIDA) 和苯甲酸的结合使用大大促进了相应的 [3 + 3] 环化过程。这种新开发的策略具有非凡的化学选择性、良好的官能团耐受性以及保留了酮基底物的羰基，从而为产物的进一步转化提供了可能。

引用次数: 0

Rh(II) catalyzed efficient sigmatropic rearrangement reaction of pyridotriazoles and sulfides Rh(II)催化吡啶三唑和硫化物的高效西格玛重排反应

Green Synthesis and Catalysis

Pub Date : 2024-05-01 DOI: 10.1016/j.gresc.2023.04.004

Yuting Chen , Guanghui Lv , Zhiyang Li , Meiling Ye , Tianle Huang , Li Hai , Yong Wu

The [2,3]- and [1,2]-sigmatropic rearrangement reactions between pyridotriazoles and sulfides catalyzed by rhodium(II) were investigated. The utilization of pyridotriazoles as the carbene precursors in this kind of reaction efficiently constructed the C(sp³)-S and C(sp³)-Se bond with broad substrate scope and great functional group tolerance.

研究了铑(II)催化的吡啶三唑与硫化物之间的[2,3]-和[1,2]-异相重排反应。在这种反应中，利用吡啶三唑作为碳烯前体，可以有效地构建 C(sp3)-S 和 C(sp3)-Se 键，具有广泛的底物范围和很强的官能团耐受性。

引用次数: 0

Photochemical nitrene transfer reactions of iminoiodinanes with sulfoxides 亚氨基碘烷与硫氧化物的光化学芘转移反应

Green Synthesis and Catalysis

Pub Date : 2024-05-01 DOI: 10.1016/j.gresc.2024.05.001

Xuemei Zhao, Zhiyuan Tang, Linlin Shi, Yujing Guo, Rene M. Koenigs, Xinqi Hao

引用次数: 0

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