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A Continuous Flow Protocol for the Synthesis of Alkenyl Thioethers Based on the Photochemical Activation of Halogen-Bonding Complexes 基于卤素键合物光化学活化的烯基硫醚连续流合成方案
IF 2 4区 化学 Q3 CHEMISTRY, ORGANIC Pub Date : 2024-06-15 DOI: 10.1055/a-2346-1091
Helena F. Piedra, Carlos Valdes, M. Plaza
Herein, we report a useful flow protocol for the preparation of alkenyl thioethers from alkenyl bromides and thiols in basic media with visible light irradiation. The reactions exhibit a wide functional group tolerance, proceed under mild conditions, are stereoselective and do not require the use of catalysts. The transformations could be successfully scaled up to 5 mmol scale without compromising yield. The key to the success of these reactions is the photochemical excitation of halogen-bonding complexes to form alkenyl and sulfur-centered radicals, a protocol recently developed in our laboratories.
在此,我们报告了在可见光照射下,在碱性介质中利用烯基溴和硫醇制备烯基硫醚的有效流程方案。该反应具有广泛的官能团耐受性,在温和的条件下进行,具有立体选择性,且无需使用催化剂。在不影响产率的情况下,这些转化反应可成功放大到 5 毫摩尔的规模。这些反应成功的关键在于光化学激发卤键络合物形成以烯基和硫为中心的自由基,这是我们实验室最近开发的一种方案。
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引用次数: 0
SYNFORM ISSUE 2024/07 第 2024/07 期
IF 2 4区 化学 Q2 Chemistry Pub Date : 2024-06-14 DOI: 10.1055/s-0043-1763988
M. Zanda
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引用次数: 0
Ni(OTf)2-Catalyzed Michael Addition Reactions of 4-Hydroxycoumarins to α,β-Unsaturated 2-Acyl Imidazoles Ni(OTf)2 催化的 4-羟基香豆素与 α、β-不饱和 2-酰基咪唑的迈克尔加成反应
IF 2 4区 化学 Q3 CHEMISTRY, ORGANIC Pub Date : 2024-06-14 DOI: 10.1055/a-2310-0924
Honghong Wang, Fan Gong, Ping Xue, Helin Lu, Xiaobo Wang, Jun Gong

An efficient Michael addition of 4-hydroxycoumarins to α,β-unsaturated 2-acyl imidazoles catalyzed by Ni(OTf)2 as a Lewis acid has been developed. A series of 4-hydroxycoumarin derivatives were obtained in excellent yields (up to 96%) with a 2 mol% catalyst loading under mild conditions. Additionally, when a chiral-at-metal rhodium complex was used as the catalyst, moderate enantioselectivity was observed (74% ee).

在作为路易斯酸的 Ni(OTf)2 催化下,研究人员开发了一种将 4-羟基香豆素与 α、β-不饱和 2-酰基咪唑进行高效迈克尔加成的方法。在温和的条件下,催化剂负载量为 2 摩尔%时,可获得一系列 4-羟基香豆素衍生物,收率极高(高达 96%)。此外,当使用手性金属铑络合物作为催化剂时,还观察到了适度的对映体选择性(74% ee)。
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引用次数: 0
Electrosynthesis of Quinoxalines via Intermolecular Cyclization/Dehydrogenation of Ketones with o-Phenylenediamines 通过酮与邻苯二胺的分子间环化/脱氢反应电合成喹喔啉类化合物
IF 2 4区 化学 Q3 CHEMISTRY, ORGANIC Pub Date : 2024-06-14 DOI: 10.1055/a-2339-2832
Yi Tao, Jiahui Zhang, Yangyang Hu, Huiying Liu, Jingwen Sun, Lei Liu

In this study, we proposed a novel electrochemical dehydrogenative synthetic method for preparing 2-substituted quinoxalines by intermolecular cyclization of aryl alkyl ketones and o-phenylenediamines. This method gave various quinoxalines in yields ranging from 35% to 71%. This novel protocol employs mild reaction conditions and offers moderate to excellent yields, a wide substrate scope, and broad functional-group compatibility. Furthermore, a late-stage functionalization and the wide substrate scope demonstrated the synthetic utility of this protocol.

在这项研究中,我们提出了一种新型的电化学脱氢合成方法,通过芳基烷基酮和邻苯二胺的分子间环化来制备 2-取代的喹喔啉类化合物。这种方法可以制备出各种喹喔啉类化合物,收率在 35% 到 71% 之间。这种新型方案采用温和的反应条件,具有中等到极好的产率、广泛的底物范围和广泛的官能团兼容性。此外,后期官能化和广泛的底物范围也证明了该方法的合成实用性。
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引用次数: 0
Nickel-Catalyzed Regio- and Enantioselective Hydrofluorination in Unactivated Alkenes 镍催化未活化烯烃的区域和对映选择性氢氟化反应
IF 2 4区 化学 Q3 CHEMISTRY, ORGANIC Pub Date : 2024-06-13 DOI: 10.1055/a-2334-6568
Minseok Kim, Seunghoon Han, Sungwoo Hong

While enantioselective hydrofluorination methods for activated alkenes represent a notable advance, the resultant enantiomeric excesses remain largely moderate, indicating the necessity for enhancements in precision, efficiency, and scope. We have recently developed an innovative nickel hydride catalytic system that enables regio- and enantioselective C–F bond formation with unactivated alkenes. By utilizing specially designed Bn-BOx ligands for improved selectivity, our approach demonstrates exceptional efficiency and selectivity with β,γ-alkenyl amide substrates. This breakthrough enhances the synthesis of organofluorine compounds, marking a significant advancement in organic synthesis.

1 Introduction

2 Reaction Design of Hydrofluorination

3 Regio- and Enantioselective Hydrofluorination

4 Asymmetric Amplification

5 Conclusions

虽然活化烯烃的对映体选择性氢氟化方法是一个显著的进步,但由此产生的对映体过剩量仍然基本适中,这表明有必要提高精确度、效率和范围。我们最近开发了一种创新的氢化镍催化系统,它能使未活化的烯烃形成具有区域和对映体选择性的 C-F 键。通过利用专门设计的 Bn-BOx 配体来提高选择性,我们的方法在处理 β、γ-烯基酰胺底物时表现出了卓越的效率和选择性。这一突破增强了有机氟化合物的合成,标志着有机合成领域的重大进展。1 引言 2 氢氟化反应设计 3 区域和对映选择性氢氟化反应 4 不对称放大 5 结论
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引用次数: 0
Electromediated Alcohol-Based Passerini-Type Reaction 基于酒精的电促进帕塞里尼式反应
IF 2 4区 化学 Q3 CHEMISTRY, ORGANIC Pub Date : 2024-06-12 DOI: 10.1055/a-2333-8596
Alexandre Simon, Sylvestre P. J. T. Bachollet, Na Pan, Laurence Grimaud, Maxime R. Vitale

An electrochemical variant of the alcohol-based oxidative Passerini reaction is reported here. It relies on an indirect anodic oxidation process followed by a three-component coupling, in which TEMPO serves as a key redox mediator. This electrochemical approach permits to operate without the need for a metal catalyst nor oxygen atmosphere and allows the use of nonactivated alcohols as reaction partners. It could be applied to the preparation of good variety of α-acyloxy-carboxamides in yields ranging from 24% to 80%.

本文报告了一种基于酒精的帕塞里尼氧化反应的电化学变体。该反应依赖于间接阳极氧化过程,然后进行三组分耦合,其中 TEMPO 是关键的氧化还原介质。这种电化学方法无需金属催化剂,也不需要氧气环境,可以使用非活化醇作为反应伙伴。该方法可用于制备多种α-乙酰氧基羧酰胺,产率在 24% 至 80% 之间。
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引用次数: 0
Heterogenization of [Ru(bpy)3]Cl2 on Ordered Mesoporous Silica Materials for Photocatalytic Applications 有序介孔二氧化硅材料上的[Ru(py)3]Cl2异质化,用于光催化应用
IF 2 4区 化学 Q3 CHEMISTRY, ORGANIC Pub Date : 2024-06-11 DOI: 10.1055/a-2317-3672
Malik Sebbat, Anish Lazar, Claire Laurent, Christelle Despas, Neus Vilà, Alain Walcarius, Nathan McClenaghan, Emmanuel Oheix, Bénédicte Lebeau, Morgan Cormier, Jean-Philippe Goddard

Herein, the preparation and characterization of three Ru-based heterogeneous photocatalysts supported on ordered mesoporous silica materials are reported. The photocatalytic activity of these catalysts was evaluated through oxidation, reduction, cycloaddition, and carboxylation reactions and their efficiencies are comparable to the parent [Ru(bpy)3]Cl2 under homogeneous conditions. These photocatalysts are efficiently recovered even after five reaction cycles offering new opportunities in sustainable chemistry.

本文报告了以有序介孔二氧化硅材料为支撑的三种 Ru 基异相光催化剂的制备和表征。通过氧化、还原、环加成和羧化反应评估了这些催化剂的光催化活性,在均相条件下,它们的效率与母体 [Ru(bpy)3]Cl2 相当。这些光催化剂在经过五个反应循环后仍能有效回收,为可持续化学提供了新的机遇。
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引用次数: 0
Photoredox and Cobalt Co-catalyzed Dehydrogenative Ring-opening/Functionalization of Mono-donor Cyclopropanes 光氧化和钴协同催化的单给体环丙烷脱氢开环/官能化反应
IF 2 4区 化学 Q3 CHEMISTRY, ORGANIC Pub Date : 2024-06-11 DOI: 10.1055/a-2342-8284
Jiyao Zhang, Haohao Huang, Zhijun Zuo
Catalytic ring-opening/functionalization of unactive cyclopropanes has proven to be a significant but challenging task in organic synthesis. Herein, we disclose the photoredox and cobalt co-catalyzed ring-opening/acceptorless dehydrogenative functionalization of mono-donor cyclopropanes, which provides a promising platform to achieve a sustainable and atom-economic approach to assemble allylic N-acyl-acetal derivatives. The reaction features mild condition, broad substrate scopes and excellent functional group compatibilities. The optimized conditions accommodate various cycloalkylamides and primary, secondary and tertiary alcohols, with applications in late-stage functionalization of pharmaceutically relevant compounds, stimulating the further utility in medicinal chemistry. Selective nucleophilic substitutions and further transformations of desired products with various carbon nucleophiles were succeed in a one-pot fashion, thus offering diverse acyclic or cyclic derivatives.
事实证明,非活性环丙烷的催化开环/功能化是有机合成中一项重要但具有挑战性的任务。在此,我们揭示了光氧和钴协同催化单给体环丙烷的开环/无受体脱氢官能化,这为实现可持续的、原子经济的烯丙基 N-酰基乙醛衍生物组装方法提供了一个前景广阔的平台。该反应具有条件温和、底物范围广和官能团兼容性好的特点。优化后的条件适用于各种环烷基酰胺和伯、仲、叔醇,可应用于医药相关化合物的后期官能化,从而促进其在药物化学中的进一步应用。选择性亲核取代和所需产物与各种碳亲核物的进一步转化均以一锅方式完成,从而提供了多种无环或环状衍生物。
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引用次数: 0
Metal-Free Synthesis of 2-Benzylideneindolin-3-ones via a Nucleophilic/Rearrangement/Azide-Alkene Cascade Reaction 通过亲核/重排/叠氮-烯级联反应无金属合成 2-苄叉吲哚啉-3-酮
IF 2 4区 化学 Q3 CHEMISTRY, ORGANIC Pub Date : 2024-06-10 DOI: 10.1055/a-2341-9185
Quan Tang, Hua Wang, Tianyu Long, Han-Han Kong, Qing-Qing Yang, Nianyu Huang, Long Wang
A metal-free synthesis of 2-benzylideneindolin-3-ones via a formal [4+1] annulation reaction from o-azidobenzaldehydes and terminal alkynes has been developed. The method features operational simplicity, mild reaction conditions and ready availability of starting materials. A broad range of 2-benzylideneindolin-3-ones were prepared in moderate to excellent yields. Mechanism studies indicated that the reaction may proceed via a nucleophilic addition/rearrangement/azide-alkene cycloaddition pathway to produce 2-benzylideneindolin-3-ones.
本研究开发了一种无金属合成 2-亚苄基吲哚啉-3-酮的方法,该方法是通过邻氮代苯甲醛和末端炔烃的形式化 [4+1] 环化反应合成 2-亚苄基吲哚啉-3-酮。该方法具有操作简单、反应条件温和、起始原料易得等特点。该方法制备了多种 2-亚苄基吲哚啉-3-酮,收率从中等到极佳。机理研究表明,该反应可通过亲核加成/重排/叠氮-烯环加成途径生成 2-亚苄基吲哚啉-3-酮。
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引用次数: 0
Efficient synthesis of fluorene derivatives via benzannulation of indene dienes with benzoylacetonitrile catalyzed by lipase 在脂肪酶催化下,通过苯甲酰乙腈与茚二烯的苯并环化作用高效合成芴衍生物
IF 2 4区 化学 Q3 CHEMISTRY, ORGANIC Pub Date : 2024-06-10 DOI: 10.1055/a-2341-9274
WENHAN SHI, Yiyao Wang, Fengxi Li, HANQING XIE, Lei Wang, Rui-Qiao Zhao, Zhi Wang
In this work, an enzymatic method for the synthesis of fluorene derivatives via benzannulation of indene dienes with benzoylacetonitrile in non-aqueous solvent was developed. Under the optimal reaction condition (indene diene (0.5 mmol), benzoylacetonitrile (0.5 mmol), ethanol (2 mL), lipase from porcine pancreas (5 mg), 50℃, 24 h.), fluorenes bearing different groups were obtained in satisfactory yields (83 %-93 %). This method not only offers a significant advancement in the synthesis of fluorene derivatives , but also mines a new application of lipase in enzyme catalytic promiscuity.
本研究开发了一种在非水溶剂中通过茚二烯与苯甲酰乙腈的苯腈化反应合成芴衍生物的酶法。在最佳反应条件(茚二烯(0.5 毫摩尔)、苯甲酰乙腈(0.5 毫摩尔)、乙醇(2 毫升)、猪胰脂肪酶(5 毫克)、50℃、24 小时)下,获得了不同基团的芴,产率令人满意(83 %-93 %)。该方法不仅在芴衍生物的合成方面取得了重大进展,而且为脂肪酶在酶催化杂化方面的应用开辟了新途径。
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