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Catalytic Transformations of Alkenes via Nickelacycles
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2024-06-28 DOI: 10.1039/d4qo00737a
Meng-Ying Qian, Kai-Xiang Zhang, Li-Jun Xiao
{"title":"Catalytic Transformations of Alkenes via Nickelacycles","authors":"Meng-Ying Qian, Kai-Xiang Zhang, Li-Jun Xiao","doi":"10.1039/d4qo00737a","DOIUrl":"https://doi.org/10.1039/d4qo00737a","url":null,"abstract":"Alkenes are fundamental components in synthetic chemistry, extensively used in the production of complex molecules for pharmaceuticals, materials science, and agrochemicals. Nickel-catalyzed transformations of alkenes via nickelacycle intermediates, formed by the oxidative cyclization of alkenes with other π-components on Ni(0), offer a promising approach characterized by high atom and step economy. Although numerous C–C bond formation reactions involving nickelacycles have been widely studied, there is a notable scarcity of comprehensive reviews that focus on transformations of alkenes. Recent progress in ligand design has enhanced control reactivity and selectivity, enabling a variety of nickel-catalyzed couplings. These include reactions of alkenes with carbon dioxide, isocyanates, alkynes, α,β-unsaturated carbonyls, aldehydes, ketones, and imines. This lack of in-depth discussion highlights the need for a detailed review that encompasses recent advancements in this field. This review summarizes these recent developments in nickel-catalyzed transformations of alkenes via nickelacycles, highlighting the advantages and challenges of this innovative strategy. The goal is to inspire new researchers to explore and contribute to this dynamic field, emphasizing nickelacycle intermediates as versatile tools for effective reactions with various π-components and identifying them as promising avenues for future research.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":null,"pages":null},"PeriodicalIF":5.4,"publicationDate":"2024-06-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141462560","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Palladium(II)-Catalyzed 1,3-Heteroaryl Acyloxylation of Propargylic Electrophiles
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2024-06-27 DOI: 10.1039/d4qo00869c
Shenghan Teng, Peiyao Liang, Lin Hu, Siyi Chen, Shoulei Wang, Wei Huang
{"title":"Palladium(II)-Catalyzed 1,3-Heteroaryl Acyloxylation of Propargylic Electrophiles","authors":"Shenghan Teng, Peiyao Liang, Lin Hu, Siyi Chen, Shoulei Wang, Wei Huang","doi":"10.1039/d4qo00869c","DOIUrl":"https://doi.org/10.1039/d4qo00869c","url":null,"abstract":"We report a 1,3-heteroaryl acyloxylation of 3-substituted propargylic esters with readily available heteroarenes including indoles, pyrroles, furans and thiophenes under palladium catalysis. The heteroaryl-functionalized Z-enol ester products are obtained in a single step with complete levels of γ-regioselectivity and anti-hydroacetoxylation stereocontrol. The use of palladium-tri(2-furyl)phosphine complex in polyfluorinated alcoholic solvents has proven to be crucial to the reactivity of the desired pathway based on control experiments. High atom economy, mild conditions (30 °C) and broad functional group tolerance make this protocol attractive. Finally, the synthetic utility of this method is demonstrated by gram-scale synthesis and downstream derivatizations of the product.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":null,"pages":null},"PeriodicalIF":5.4,"publicationDate":"2024-06-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141461948","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Green synthesis of glutaramides, piperidino[1,2-a]benzimidazol-1-ones and N-cyclopentenyl benzimidazolones enabled by microwave assisted domino reactions of cyclic 2-diazo-1,3-diketones with aniline derivatives 通过环状 2-重氮-1,3-二酮与苯胺衍生物的微波辅助多米诺反应实现戊二酰胺、哌啶并[1,2-a]苯并咪唑-1-酮和 N-环戊烯基苯并咪唑酮的绿色合成
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2024-06-26 DOI: 10.1039/d4qo00613e
Cheng Zhao, Xiao-Wei Hu, Yi-Bing Xu, Xiong-Wei Liu, You-Ping Tian, Yun-Lin Liu
{"title":"Green synthesis of glutaramides, piperidino[1,2-a]benzimidazol-1-ones and N-cyclopentenyl benzimidazolones enabled by microwave assisted domino reactions of cyclic 2-diazo-1,3-diketones with aniline derivatives","authors":"Cheng Zhao, Xiao-Wei Hu, Yi-Bing Xu, Xiong-Wei Liu, You-Ping Tian, Yun-Lin Liu","doi":"10.1039/d4qo00613e","DOIUrl":"https://doi.org/10.1039/d4qo00613e","url":null,"abstract":"Microwave assisted divergent domino reactions between cyclic 2-diazo-1,3-diketones and aniline derivatives selectively leading to either glutaramides, piperidino[1,2-a]benzimidazol-1-ones or N-cyclopentenyl benzimidazolones are described. This synthetic protocol features easy operation, shrort reaction time, and environmental friendliness.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":null,"pages":null},"PeriodicalIF":5.4,"publicationDate":"2024-06-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141453101","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
A Novel Approach to the Tetracyclic Frameworks of Anislactone-type Sesquiterpenoids 研究茴香内酯类四环框架的新方法
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2024-06-26 DOI: 10.1039/d4qo00915k
Long He, Xiaocheng Zhang, Sen Li, Xuexue Tian, Yimeng Han, Haitao Xie, Weiqing Xie
{"title":"A Novel Approach to the Tetracyclic Frameworks of Anislactone-type Sesquiterpenoids","authors":"Long He, Xiaocheng Zhang, Sen Li, Xuexue Tian, Yimeng Han, Haitao Xie, Weiqing Xie","doi":"10.1039/d4qo00915k","DOIUrl":"https://doi.org/10.1039/d4qo00915k","url":null,"abstract":"Herein, we present a novel approach to construct the A-B-C-D ring system of anislactone-type sesquiterpenoids. This innovative strategy involves a H2O2-mediated oxidative ring contraction reaction to form a 5/5 fused skeleton, while simultaneously generating contiguous quaternary carbon centers (CQCCs). Additionally, the γ-lactones (A- and D- rings) are assembled through Pummerer reaction initiated cyclization and sequential Mukaiyama hydration/translactonization, respectively. Despite our efforts to introduce a hydroxyl group at C7 via C-H oxidation, these endeavors ultimately proved unsuccessful.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":null,"pages":null},"PeriodicalIF":5.4,"publicationDate":"2024-06-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141453143","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Copper-catalyzed Annulation Reaction of Diazo Esters with Propargyl Amines for the Synthesis of 2,5-Dihydropyrroles 铜催化重氮酯与丙炔胺的环化反应以合成 2,5-二氢吡咯
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2024-06-26 DOI: 10.1039/d4qo00751d
Haodong Xie, Wei Zhao, Heping Wei, Yang Yu, Lili Zhao, Jonathan B. Baell, Fei Huang
{"title":"Copper-catalyzed Annulation Reaction of Diazo Esters with Propargyl Amines for the Synthesis of 2,5-Dihydropyrroles","authors":"Haodong Xie, Wei Zhao, Heping Wei, Yang Yu, Lili Zhao, Jonathan B. Baell, Fei Huang","doi":"10.1039/d4qo00751d","DOIUrl":"https://doi.org/10.1039/d4qo00751d","url":null,"abstract":"2,5-Dihydropyrrole derivatives are considered privileged structures as reflected by their presence in many biological activities and therapeutic agents. Herein, we develop a concise and efficient method utilizing a commercially available copper salt as catalyst to facilitate the formation of 2,5-dihydropyrrole from propargyl amine and diazo ester. This reaction proceeds via the formation of N-ylide followed by bond cleavage/recombination. Control experiments and density functional theory (DFT) calculations provide a detailed analysis of the reaction pathway. The key features of this protocol include simple operation, readily available starting materials, mild conditions, and high atom economy. In addition, the gram-scale preparation experiment and the transformations of 2,5-dihydropyrroles demonstrate the potential applicability of our synthetic method.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":null,"pages":null},"PeriodicalIF":5.4,"publicationDate":"2024-06-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141452814","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Photocatalytic C-P bonds formation based on the reaction of carbon-centered radicals with phosphides 基于碳中心自由基与磷化物反应的光催化 C-P 键形成
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2024-06-25 DOI: 10.1039/d4qo00933a
Shi-Yi Zhao, Yi-Yun Huang, Shi-Hao Deng, Zhi-Peng Guan, Zhi-Bing Dong
{"title":"Photocatalytic C-P bonds formation based on the reaction of carbon-centered radicals with phosphides","authors":"Shi-Yi Zhao, Yi-Yun Huang, Shi-Hao Deng, Zhi-Peng Guan, Zhi-Bing Dong","doi":"10.1039/d4qo00933a","DOIUrl":"https://doi.org/10.1039/d4qo00933a","url":null,"abstract":"Organophosphorus compounds hold significant importance in the fields of materials science, medicinal chemistry, pesticides and organic synthesis. In particular, alkyl phosphate compounds can be used in sensors, antibacterial, anti-virus, herbicides and organic phosphine ligands, etc. Therefore, the construction of C(sp3)-P bonds has attracted tremendous attention from chemists. Although strategies for the photocatalysis synthesis of alkyl phosphonate esters have been reported, it was mainly limited to the radical addition reaction of a few phosphines with unsaturated bond. In recent years, with the rapid development of photocatalysis, organic chemists have made remarkable progress in the study of visible light-mediated alkyl radical phosphorylation. This review focused on the synthesis of C(sp3)-P bonds by using alkyl radicals with phosphorous compounds of different valence states (PIII, PV, P4) under photocatalysis.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":null,"pages":null},"PeriodicalIF":5.4,"publicationDate":"2024-06-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141452861","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Access to Spiro-bicyclo[2.1.1]hexanes via BF3∙Et2O-Catalyzed Formal [2π + 2σ] Cycloaddition of Bicyclo[1.1.0]butanes with Benzofuran-derived Oxa(aza)dienes 通过 BF3∙Et2O 催化双环[1.1.0]丁烷与苯并呋喃衍生 Oxa(aza)二烯的正规 [2π + 2σ] 环加成获得螺双环[2.1.1]己烷
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2024-06-25 DOI: 10.1039/d4qo00511b
Wei-Ping Deng, Jia-Yi Su, Jian Zhang, Zhiyun Xin, Hao Li, Hanliang Zheng
{"title":"Access to Spiro-bicyclo[2.1.1]hexanes via BF3∙Et2O-Catalyzed Formal [2π + 2σ] Cycloaddition of Bicyclo[1.1.0]butanes with Benzofuran-derived Oxa(aza)dienes","authors":"Wei-Ping Deng, Jia-Yi Su, Jian Zhang, Zhiyun Xin, Hao Li, Hanliang Zheng","doi":"10.1039/d4qo00511b","DOIUrl":"https://doi.org/10.1039/d4qo00511b","url":null,"abstract":"Herein, we have developed a method for the construction of spiro[benzofuran-2,2'-bicyclo[2.1.1]hexanes] via BF3·Et2O-catalyzed formal [2π + 2σ] cycloaddition of bicyclo[1.1.0]butanes with benzofuran-derived oxa(aza)dienes. This transformation allowed for facile access to a variety of functionalized spiro-bicyclo[2.1.1]hexanes in good yields (up to 99% yield) with excellent chemoselectivities and a broad substrate scope (34 examples) under mild reaction conditions. Moreover, the synthetic utility of the cycloadducts was further emphasized through a scale-up experiment and subsequent synthetic transformations.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":null,"pages":null},"PeriodicalIF":5.4,"publicationDate":"2024-06-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141453022","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Palladium-Catalyzed Epoxidation of Olefins Using Electrophiles as Oxidizing Agents 以亲电体为氧化剂的钯催化烯烃环氧化反应
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2024-06-25 DOI: 10.1039/d4qo00732h
Biao Yao, Lujun Zhang, Yupeng Chen, Liren Zhang, Wanqing Wu, Huanfeng Jiang
{"title":"Palladium-Catalyzed Epoxidation of Olefins Using Electrophiles as Oxidizing Agents","authors":"Biao Yao, Lujun Zhang, Yupeng Chen, Liren Zhang, Wanqing Wu, Huanfeng Jiang","doi":"10.1039/d4qo00732h","DOIUrl":"https://doi.org/10.1039/d4qo00732h","url":null,"abstract":"A palladium-catalyzed olefin epoxidation reaction was developed using electrophilic reagents as oxidants. The modular synthesis of various alkyl alcohols, alkyl esters, and alkyl halides was achieved in good to excellent yields. These products can be used to synthesize potential drug ibuprofen derivatives. A preliminary mechanistic study shows that SN2 attack by the nucleophilic reagents in the system creates the final C–O bond and an SN1 reaction of halide ions creates a C–X bond.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":null,"pages":null},"PeriodicalIF":5.4,"publicationDate":"2024-06-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141452940","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Chemoselective Reaction of Methoxyaminomethyl BODIPYs with Unprotected Carbohydrates: A Powerful Tool for Accessing BODIPY Neoglycosides 甲氧基氨基甲基 BODIPYs 与无保护碳水化合物的化学选择性反应：获取 BODIPY 新糖苷的有力工具
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2024-06-25 DOI: 10.1039/d4qo00886c
Ana M Gomez, Luis García-Fernández, Andres G. Santana, Clara Uriel, Leire Gartzia-Rivero, Jorge Bañuelos, Inmaculada Garcia-Moreno, Lourdes Infantes, Maria Rosa Aguilar de Armas, Jose Cristobal Lopez
{"title":"Chemoselective Reaction of Methoxyaminomethyl BODIPYs with Unprotected Carbohydrates: A Powerful Tool for Accessing BODIPY Neoglycosides","authors":"Ana M Gomez, Luis García-Fernández, Andres G. Santana, Clara Uriel, Leire Gartzia-Rivero, Jorge Bañuelos, Inmaculada Garcia-Moreno, Lourdes Infantes, Maria Rosa Aguilar de Armas, Jose Cristobal Lopez","doi":"10.1039/d4qo00886c","DOIUrl":"https://doi.org/10.1039/d4qo00886c","url":null,"abstract":"The neoglycosylation of methoxyaminomethyl-appended BODIPYs with unprotected reducing mono-, di-, and trisaccharides produces, in a regio- and stereoselective manner, cyclic N-glycosyl-N-methyl-BODIPY conjugates, as a relevant class of neoglycosides that display excellent photophysical characteristics in pure water, even at high dye concentrations. In addition, the cellular uptake of some of the neoglycosylated BODIPYs has been confirmed via fluorescence microscopy, and a BODIPY-acarbose conjugate showed comparable enzymatic inhibitory activity to acarbose for two different α-amylases: A. oryzae α-amylase (AOA) and human salivary α-amylase (HSA).","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":null,"pages":null},"PeriodicalIF":5.4,"publicationDate":"2024-06-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141453053","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Nickel-catalyzed arylative cyclization of 1,6-enynes: arylation of unactivated alkene moieties 镍催化的 1,6-烯炔芳基化环化反应：未活化烯烃分子的芳基化反应
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2024-06-25 DOI: 10.1039/d4qo00784k
Jian Gao, Qi Wei, Zeqing Zhang, Zhishan Su, Jialin Ming, Yongmin Zhang
{"title":"Nickel-catalyzed arylative cyclization of 1,6-enynes: arylation of unactivated alkene moieties","authors":"Jian Gao, Qi Wei, Zeqing Zhang, Zhishan Su, Jialin Ming, Yongmin Zhang","doi":"10.1039/d4qo00784k","DOIUrl":"https://doi.org/10.1039/d4qo00784k","url":null,"abstract":"We developed a new type of catalytic arylative cyclization of 1,6-enynes, whereby an aryl group is introduced at an unactivated alkene moiety rather than at an alkyne moiety. The reaction of a 1,6-enyne with an arylboronic acid in the presence of an Ni(cod)<small><sub>2</sub></small>/P(4-MeOC<small><sub>6</sub></small>H<small><sub>4</sub></small>)<small><sub>3</sub></small> complex yields a five-membered ring product incorporating an all-carbon quaternary center. Experimental studies and extensive DFT calculations reveal that an Ni(I) species is involved in the catalytic cycle, which is an uncommon pathway involving transmetalation, cycloisomerization, selective sp3–sp2 carbon–carbon bond formation, and finally hydrolysis.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":null,"pages":null},"PeriodicalIF":5.4,"publicationDate":"2024-06-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141452930","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
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