共查询到20条相似文献,搜索用时 12 毫秒
1.
Long Huang Chen Zhu Liang Yi Huifeng Yue Rajesh Kancherla Magnus Rueping 《Angewandte Chemie (International ed. in English)》2020,59(1):457-464
Chemical transformations based on cascade reactions have the potential to simplify the preparation of diverse and architecturally complex molecules dramatically. Herein, we disclose an unprecedented and efficient method for the cross‐coupling of radical precursors, dienes, and electrophilic coupling partners via a photoredox‐ and nickel‐enabled cascade cross‐coupling process. The cascade reaction furnishes a diverse array of saturated carbo‐ and heterocyclic scaffolds, thus providing access to a quick gain in C?C bond saturation. 相似文献
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有机化合物特定位点嵌入氟原子或含氟片段,可以产生独特的生物或物理性质改变.单氟取代烯基是生物医药领域理想的酰胺键替代物,在医药化学、药物研发等方向已经获得广泛的应用.通过溴化镍(Ⅱ)二乙二醇二甲醚复合物、4,4'-二叔丁基-2,2'-二吡啶的催化体系,实现了多种氟代烯基硼酯与一级烷基卤化物碘代物、溴代物以及二级烷基溴代物的Suzuki偶联反应.该反应具有良好的收率和优秀的官能团兼容性,能够兼容酯基、氰基、醇羟基等多种具有有机合成化学价值的官能团,为单氟取代烯烃的合成提供了方法.机理实验表明该反应可能经历烷基卤化物自由基均裂历程. 相似文献
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Cross‐Coupling of Sodium Sulfinates with Aryl,Heteroaryl, and Vinyl Halides by Nickel/Photoredox Dual Catalysis 下载免费PDF全文
《Angewandte Chemie (International ed. in English)》2018,57(5):1371-1375
An efficient photoredox/nickel catalyzed sulfonylation reaction of aryl, heteroaryl, and vinyl halides has been achieved for the first time. This newly developed sulfonylation protocol provides a versatile method for the synthesis of diverse aromatic sulfones at room temperature and shows excellent functional group tolerance. The electrophilic coupling partners are not limited to aryl, heteroaryl, and vinyl bromides and iodides, but also includes less reactive aryl chlorides as suitable substrates for this transformation. 相似文献
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Highly Chemoselective Iridium Photoredox and Nickel Catalysis for the Cross‐Coupling of Primary Aryl Amines with Aryl Halides 下载免费PDF全文
Dr. Martins S. Oderinde Natalie H. Jones Antoine Juneau Prof. Mathieu Frenette Dr. Brian Aquila Sharon Tentarelli Dr. Daniel W. Robbins Dr. Jeffrey W. Johannes 《Angewandte Chemie (International ed. in English)》2016,55(42):13219-13223
A visible‐light‐promoted iridium photoredox and nickel dual‐catalyzed cross‐coupling procedure for the formation C?N bonds has been developed. With this method, various aryl amines were chemoselectively cross‐coupled with electronically and sterically diverse aryl iodides and bromides to forge the corresponding C?N bonds, which are of high interest to the pharmaceutical industries. Aryl iodides were found to be a more efficient electrophilic coupling partner. The coupling reactions were carried out at room temperature without the rigorous exclusion of molecular oxygen, thus making this newly developed Ir‐photoredox/Ni dual‐catalyzed procedure very mild and operationally simple. 相似文献
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Kirsten A. Hewitt Claire A. Herbert Alissa C. Matus Elizabeth R. Jarvo 《Molecules (Basel, Switzerland)》2021,26(19)
Herein, we report a Kumada cross-coupling reaction of benzylic sulfonamides. The scope of the transformation includes acyclic and cyclic sulfonamide precursors that cleanly produce highly substituted acyclic fragments. Preliminary data are consistent with a stereospecific mechanism that allows for a diastereoselective reaction. 相似文献
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Dr. Long Huang Dr. Chen Zhu M. Sc. Liang Yi Dr. Huifeng Yue Dr. Rajesh Kancherla Prof. Dr. Magnus Rueping 《Angewandte Chemie (Weinheim an der Bergstrasse, Germany)》2020,132(1):465-472
Chemical transformations based on cascade reactions have the potential to simplify the preparation of diverse and architecturally complex molecules dramatically. Herein, we disclose an unprecedented and efficient method for the cross-coupling of radical precursors, dienes, and electrophilic coupling partners via a photoredox- and nickel-enabled cascade cross-coupling process. The cascade reaction furnishes a diverse array of saturated carbo- and heterocyclic scaffolds, thus providing access to a quick gain in C−C bond saturation. 相似文献
7.
Dawei Zhang Xing Gao Qiao-Qiao Min Dr. Yucheng Gu Dr. Guillaume Berthon Prof. Dr. Xingang Zhang 《Chemistry (Weinheim an der Bergstrasse, Germany)》2022,28(26):e202200642
A nickel-catalyzed cross-coupling of heteroaryl halides with chlorodifluoroacetamides and chlorodifluoroacetate has been developed. The combination of NiCl2 ⋅ DME with 4,4′-diNon-bpy, co-ligand PPh3, and additive LiCl renders the catalytic system efficient for the synthesis of medicinal interest heteroaryldifluoroacetamides. The application of the method leads to short and highly efficient synthesis of biologically active molecules, providing a facile route for applications in medicinal chemistry and agrochemistry. 相似文献
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Matteo Chierchia Peilin Xu Gabriel J. Lovinger James P. Morken 《Angewandte Chemie (International ed. in English)》2019,58(40):14245-14249
A hybrid transition‐metal/radical process is described that results in the addition of organozinc reagents and alkyl halides across alkenyl boron reagents in an enantioselective catalytic fashion. The reaction can be accomplished both intermolecularly and intramolecularly, providing useful product yields and high enantioselectivities in both manifolds. 相似文献
11.
Fan Song Fang Wang Lei Guo Xiaoliang Feng Yanyan Zhang Lingling Chu 《Angewandte Chemie (International ed. in English)》2020,59(1):177-181
A stereodivergent reductive coupling reaction between allylic carbonates and vinyl triflates to furnish both E‐ and Z‐configured 1,4‐dienes has been achieved by visible‐light‐induced photoredox/nickel dual catalysis. The mild reaction conditions allow good compatibility of both vinyl triflates and allylic carbonates. Notably, the stereoselectivity of this synergistic cross‐electrophile coupling can be tuned by an appropriate photocatalyst with a suitable triplet‐state energy, providing a practical and stereodivergent means to alkene synthesis. Preliminary mechanistic studies shed some light on the coupling step as well as the control of the stereoselectivity step. 相似文献
12.
Nurtalya Alandini Luca Buzzetti Gianfranco Favi Tim Schulte Lisa Candish Karl D. Collins Paolo Melchiorre 《Angewandte Chemie (International ed. in English)》2020,59(13):5248-5253
Herein, we report a one‐electron strategy for catalytic amide synthesis that enables the direct carbamoylation of (hetero)aryl bromides. This radical cross‐coupling approach, which is based on the combination of nickel and photoredox catalysis, proceeds at ambient temperature and uses readily available dihydropyridines as precursors of carbamoyl radicals. The method's mild reaction conditions make it tolerant of sensitive‐functional‐group‐containing substrates and allow the installation of an amide scaffold within biologically relevant heterocycles. In addition, we installed amide functionalities bearing electron‐poor and sterically hindered amine moieties, which would be difficult to prepare with classical dehydrative condensation methods. 相似文献
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结合可见光促进氧化还原和镍催化的碳碳键合成研究,是对过渡金属催化的交叉偶联反应的重要补充,具有广阔的发展空间和应用前景,是近年来有机光化学合成的前沿热点领域之一。本文依据反应设计的模式划分,小结目前该领域的研究进展。 相似文献
14.
Roberto del Río-Rodríguez Laura Blanco Dr. Alba Collado Dr. Jose A. Fernández-Salas Dr. José Alemán 《Chemistry (Weinheim an der Bergstrasse, Germany)》2022,28(54):e202201644
A nickel-catalysed reductive cross-coupling reaction between benzyl sulfonium salts and benzyl bromides is reported. Simple, stable and readily available sulfonium salts have shown their ability as leaving groups in cross-electrophile coupling, allowing the formation of challenging sp3–sp3 carbon-carbon bonds, towards the synthesis of interesting dihydrostilbene derivatives. In addition, benzyl tosyl derivatives have been demonstrated to be suitable substrates for reductive cross-coupling by in-situ formation of the corresponding sulfonium salt. 相似文献
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Alessandro Cerveri Riccardo Giovanelli Davide Sella Riccardo Pedrazzani Prof. Magda Monari Dr. Olalla Nieto Faza Prof. Carlos Silva López Prof. Marco Bandini 《Chemistry (Weinheim an der Bergstrasse, Germany)》2021,27(28):7657-7662
A novel asymmetric nickel-based procedure has been developed in which CO2 fixation is achieved as a second step of a truncated Heck coupling. For this, a new chiral ligand has been prepared and shown to achieve enantiomeric excesses up to 99 %. The overall process efficiently furnishes chiral 2,3-dihydrobenzofuran-3-ylacetic acids, an important class of bioactive products, from easy to prepare starting materials. A combined experimental and computational effort revealed the key steps of the catalytic cycle and suggested the unexpected participation of Ni(I) species in the coupling event. 相似文献
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Synthesis of Non‐Classical Arylated C‐Saccharides through Nickel/Photoredox Dual Catalysis 下载免费PDF全文
Dr. Audrey Dumoulin Jennifer K. Matsui Dr. Álvaro Gutiérrez‐Bonet Prof. Gary A. Molander 《Angewandte Chemie (International ed. in English)》2018,57(22):6614-6618
The development of synthetic tools to introduce saccharide derivatives into functionally complex molecules is of great interest, particularly in the field of drug discovery. Herein, we report a new route toward highly functionalized, arylated saccharides, which involves nickel‐catalyzed cross‐coupling of photoredox‐generated saccharyl radicals with a range of aryl‐ and heteroaryl bromides, triggered by an organic photocatalyst. In contrast to existing methods, the mild reaction conditions achieve arylation of saccharide motifs while leaving the anomeric carbon available, thus providing access to a class of arylated glycosides that has been underexplored until now. To demonstrate the potential of this strategy in late‐stage functionalization, a variety of structurally complex molecules incorporating saccharide moieties were synthesized. 相似文献
18.
利用密度泛函理论(DFT)计算研究了镍催化的溴苯(R1)与对溴苯甲酸甲酯(R2)生成非对称联芳化合物的还原性交叉偶联反应的机理.结果表明,相对于一价镍的催化机理,零价镍作为活性催化剂更有利于反应的进行,零价镍催化剂首先与R1络合或者首先与R2络合的反应机理十分相似,其决速步在气相时的能垒分别是70.50或者49.66 kJ?mol-1.零价镍催化机理包括如下步骤:一次氧化加成;还原;二次氧化加成;还原消除以及催化剂再生.另外,计算结果还表明有机锌试剂在这个反应体系中很难生成. 相似文献
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Jacqkis Davis Mojgan Gharaee Dr. Chamini V. Karunaratne Jose Cortes Vazquez Mikayla Haynes Prof. Weiwei Luo Dr. Vladimir N. Nesterov Prof. Thomas Cundari Prof. Hong Wang 《Chemistry (Weinheim an der Bergstrasse, Germany)》2022,28(27):e202200224
Cooperative enamine-metal Lewis acid catalysis has emerged as a powerful tool to construct carbon-carbon and carbon-heteroatom bond forming reactions. A concise synthetic method for asymmetric synthesis of chromans from cyclohexanones and salicylaldehydes has been developed to afford tricyclic chromans containing three consecutive stereogenic centers in good yields (up to 87 %) and stereoselectivity (up to 99 % ee and 11 : 1 : 1 dr). This difficult organic transformation was achieved through bifunctional enamine-metal Lewis acid catalysis. It is believed that the strong activation of the salicylaldehydes through chelating to the metal Lewis acid and the bifunctional nature of the catalyst accounts for the high yields and enantioselectivity of the reaction. The absolute configurations of the chroman products were established through X-ray crystallography. DFT calculations were conducted to understand the mechanism and stereoselectivity of this reaction. 相似文献
20.
Liu Yang Huan-Huan Lu Chu-Hui Lai Dr. Gang Li Prof. Dr. Wei Zhang Prof. Dr. Rui Cao Prof. Dr. Fengyi Liu Dr. Chao Wang Prof. Dr. Jianliang Xiao Prof. Dr. Dong Xue 《Angewandte Chemie (Weinheim an der Bergstrasse, Germany)》2020,132(31):12814-12819
A highly effective C−O coupling reaction of (hetero)aryl electrophiles with primary and secondary alcohols is reported. Catalyzed by a NiII-aryl complex under long-wave UV (390–395 nm) irradiation in the presence of a soluble amine base without any additional photosensitizer, the reaction enables the etherification of aryl bromides and aryl chlorides as well as sulfonates with a wide range of primary and secondary aliphatic alcohols, affording synthetically important ethers. Intramolecular C−O coupling is also possible. The reaction appears to proceed via a NiI–NiIII catalytic cycle. 相似文献