Organic Chemistry Frontiers最新文献

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Recent advances in post Ugi-4CR dearomatizations for constructing spiro heterocycles 用于构建螺杂环的 Ugi-4CR 后脱芳香化反应的最新进展
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2024-07-12 DOI: 10.1039/d4qo01060d
Xiao Tang, Qianqian Tao, Liangliang Song, Erik V Van der Eycken
{"title":"Recent advances in post Ugi-4CR dearomatizations for constructing spiro heterocycles","authors":"Xiao Tang, Qianqian Tao, Liangliang Song, Erik V Van der Eycken","doi":"10.1039/d4qo01060d","DOIUrl":"https://doi.org/10.1039/d4qo01060d","url":null,"abstract":"The Ugi reaction has obtained broad interest due to mild reaction conditions and high variability. The versatile Ugi adducts provide myriad opportunities for post-transformations, leading to countless heterocycles, bioactive molecules, macrocycles, polymers, natural products and drugs. Recently, dearomatization strategies have been employed in post-Ugi transformations. Through transition metal catalysis and metal-free methods, different kinds of three dimensional complex molecules are formed in an atom- and step-economic manner. This review summarizes recent advances in the combination of the Ugi-4CR and dearomatization strategies for the synthesis of spirocycles.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":null,"pages":null},"PeriodicalIF":5.4,"publicationDate":"2024-07-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141597549","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
Photoredox/Cu dual catalyzed 1,4-cyanosulfonylation enabled by remote cyano migration 光氧化/铜双催化 1,4-氰基磺酰化作用可实现氰基远程迁移
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2024-07-12 DOI: 10.1039/d4qo00827h
Xiaofei Xie, Yan Li, Zhengyuan Bo, Yingguang Zhu, Kang Chen
{"title":"Photoredox/Cu dual catalyzed 1,4-cyanosulfonylation enabled by remote cyano migration","authors":"Xiaofei Xie, Yan Li, Zhengyuan Bo, Yingguang Zhu, Kang Chen","doi":"10.1039/d4qo00827h","DOIUrl":"https://doi.org/10.1039/d4qo00827h","url":null,"abstract":"A photoredox/Cu dual catalyzed 1,4-cyanosulfonylation of NHPI esters with readily available sodium arylsulfinates has been established under mild conditions, which provides an expedient approach to a variety of δ-sulfonyl nitriles with good regioselectivity and functional group tolerance. A mechanism involving the decarboxylation-triggered remote cyano migration has been proposed.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":null,"pages":null},"PeriodicalIF":5.4,"publicationDate":"2024-07-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141597396","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
Electrooxidative iridium-catalyzed sp2 C−H activation-annulation leading to cationic π-extended heteroaromatics 电氧化铱催化 sp2 C-H 活化-annulation,产生阳离子π-扩展杂芳烃
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2024-07-12 DOI: 10.1039/d4qo01019a
Qi-Liang Yang, Na-Na Guo, Shu-Xian Liu, Bei-Ning Zhang, Guo-Dong Zou, Dong-Chao Wang, Haixia Wang, Hai-Ming Guo
{"title":"Electrooxidative iridium-catalyzed sp2 C−H activation-annulation leading to cationic π-extended heteroaromatics","authors":"Qi-Liang Yang, Na-Na Guo, Shu-Xian Liu, Bei-Ning Zhang, Guo-Dong Zou, Dong-Chao Wang, Haixia Wang, Hai-Ming Guo","doi":"10.1039/d4qo01019a","DOIUrl":"https://doi.org/10.1039/d4qo01019a","url":null,"abstract":"This study demonstrates an electrochemically driven, Ir(III)-catalyzed method for pyridine-, azo-, and purine-directed olefinic and aromatic C(sp2)−H activation and regioselective annulation with alkynes for the synthesis of biologically useful quaternary ammonium salts. This approach notably eliminates the need for stoichiometric amounts of external oxidants, offering a broader substrate scope along with improved product regioselectivity under mild electrolysis conditions as compared to previously employed strong oxidant conditions. Detailed mechanistic insights, including the isolation, characterization, and cyclovoltammetric analysis of catalytically relevant iridium(III) and iridium(I) intermediates, provided strong supporting evidence for an Ir(III/I) catalytic cycle operation.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":null,"pages":null},"PeriodicalIF":5.4,"publicationDate":"2024-07-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141597431","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
X-ray Characterization of core-modified N-confused fused porphyrinogen and genesis of () (anti)Aromatic N-confused fused porphyrinoids 核心修饰的 N-混淆融合卟啉原的 X 射线特征和 () (反)芳香族 N-混淆融合卟啉的形成
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2024-07-11 DOI: 10.1039/d4qo01162g
Harapriya Rath, Manik Jana, Gunasekaran Velmurugan, Peter Comba
{"title":"X-ray Characterization of core-modified N-confused fused porphyrinogen and genesis of () (anti)Aromatic N-confused fused porphyrinoids","authors":"Harapriya Rath, Manik Jana, Gunasekaran Velmurugan, Peter Comba","doi":"10.1039/d4qo01162g","DOIUrl":"https://doi.org/10.1039/d4qo01162g","url":null,"abstract":"Rational synthesis, spectroscopic and solid-state structural isolation of an unprecedented core modified N-confused fused porphyrinogen 7 as a single isomer has been achieved in near quantitative yield. The solid-state crystal structure reveals a non planar structure as a result of four sp3 meso carbons for 7. All possible stereoisomers of the S2N3 hybrid N-confused fused porphyrinogen 7 have been unravelled via thorough DFT studies. The genesis of the porphyrinogen-porpho(mono/di)methene-porphyrin skeleton rearrangements have been unravelled via controlled chemical oxidation methods. The  and  (anti)aromaticity of the porphyrinoids 9 and 10 have been thoroughly investigated via spectroscopic and in-depth DFT studies.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":null,"pages":null},"PeriodicalIF":5.4,"publicationDate":"2024-07-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141584522","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 Allenynylative C–P Couplings of Diynylic Acetates with Hydrophosphoryl Compounds Leading to Phosphorylated Allenynes 铜催化二炔基乙酸酯与氢磷酸化合物的 C-P 偶联反应,生成磷酸化烯炔类化合物
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2024-07-10 DOI: 10.1039/d4qo01021c
Shaoqing Liu, Kaixin Yin, Yishuai Fan, Li-Biao Han, Ruwei Shen
{"title":"Copper-Catalyzed Allenynylative C–P Couplings of Diynylic Acetates with Hydrophosphoryl Compounds Leading to Phosphorylated Allenynes","authors":"Shaoqing Liu, Kaixin Yin, Yishuai Fan, Li-Biao Han, Ruwei Shen","doi":"10.1039/d4qo01021c","DOIUrl":"https://doi.org/10.1039/d4qo01021c","url":null,"abstract":"A highly efficient copper-catalyzed coupling reaction of diynylic acetates with hydrophosphoryl compounds is developed based on a concept of site-selective nucleophilic interception of copper-cumulenylidene-type intermediates. This reaction provides an expeditious synthesis of a novel class of conjugated allenynylphosphoryl compounds in good to high yields from readily available materials under mild conditions.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":null,"pages":null},"PeriodicalIF":5.4,"publicationDate":"2024-07-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141566054","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
Photoredox-Enabled Ring-Opening of Cyclobutanes via the Formation of a Carbon Radical 通过形成碳自由基实现环丁烷的光氧化开环作用
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2024-07-10 DOI: 10.1039/d4qo00996g
Chunhang Zhao, Wenjing Ma, Kairui Liu, Ruoyang Xu, Xiuya Ma, Yan Zhang
{"title":"Photoredox-Enabled Ring-Opening of Cyclobutanes via the Formation of a Carbon Radical","authors":"Chunhang Zhao, Wenjing Ma, Kairui Liu, Ruoyang Xu, Xiuya Ma, Yan Zhang","doi":"10.1039/d4qo00996g","DOIUrl":"https://doi.org/10.1039/d4qo00996g","url":null,"abstract":"The high strain energy of cyclobutanes has been utilized for the selective ring-opening, enabling the synthesis of valuable linear aliphatic compounds. Although significant progress was observed recently, most of the approaches appear to be limited to two major manifolds, namely transition metal catalyzed carbon–carbon (C–C) oxidative addition or cyclobutyloxy radical-initiated ring opening. In sharp contrast, we describe the photoinduced C–C activation through a cyclobutylcarbinyl radical to access γ,δ-unsaturated ketones obtained from cyclobutyl tertiary alcohol and sulfonyl chlorides through the strain release strategy associated with the formation of a stabilized radical. Furthermore, the ketocarbonyl group also enabled diverse post-synthetic modifications. Overall, out approach is characterized by broad functional group tolerance, ample substrate scope, and scalability. Our findings represent an alternative method to the aforementioned methods for remote 1,4-difunctionalizations, accompanied by a synthetically useful C–C double bond persisting in the obtained products.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":null,"pages":null},"PeriodicalIF":5.4,"publicationDate":"2024-07-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141566051","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
Asymmetric Synthesis of 1H-pyrazolo[3,4-b]pyridine Analogues Catalyzed by Chiral-at-Metal Rh(III) Complexes 在手性金属 Rh(III) 配合物催化下不对称合成 1H-吡唑并[3,4-b]吡啶类似物
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2024-07-10 DOI: 10.1039/d4qo01100g
Xiang Ji, Shijie Zhu, Yongsheng Li, Zhifei Zhao, Shi-Wu Li
{"title":"Asymmetric Synthesis of 1H-pyrazolo[3,4-b]pyridine Analogues Catalyzed by Chiral-at-Metal Rh(III) Complexes","authors":"Xiang Ji, Shijie Zhu, Yongsheng Li, Zhifei Zhao, Shi-Wu Li","doi":"10.1039/d4qo01100g","DOIUrl":"https://doi.org/10.1039/d4qo01100g","url":null,"abstract":"An efficient asymmetric Friedel-Craft-type alkylation /Cyclization of 5-aminopyrazoles with α,β-unsaturated 2-acyl imidazoles has been developed, affording the corresponding pyrazolo[3,4-b] pyridine analogues in 81-98% yield with 85-99% enantioselectivity. Remarkably, this protocol exhibits extraordinary advantages in terms of reactivity and enantioselectivity, given the fact that as low as 0.05 mol % of chiral Rh(III) complex can promote the title reaction on gram scale to afford desired product with excellent enantioselectivity (96% ee). Application of the methodology in an efficient synthesis of pyrazolo[3,4-b] pyridine via dehydrogenation, is reported.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":null,"pages":null},"PeriodicalIF":5.4,"publicationDate":"2024-07-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141566052","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
Total Synthesis of (‒)-Deglycocadambine (-)-Deglycocadambine 的全合成
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2024-07-10 DOI: 10.1039/d4qo01122h
Fang-Xin Wang, Ying-Tao Chen, Hui Liu, Hengshan Wang, Hong Liang, Zhen-Feng Chen, Yonggui Robin Chi
{"title":"Total Synthesis of (‒)-Deglycocadambine","authors":"Fang-Xin Wang, Ying-Tao Chen, Hui Liu, Hengshan Wang, Hong Liang, Zhen-Feng Chen, Yonggui Robin Chi","doi":"10.1039/d4qo01122h","DOIUrl":"https://doi.org/10.1039/d4qo01122h","url":null,"abstract":"The first total synthesis of monoterpene indole alkaloid (–)-deglycocadambine is achieved in 12 steps with (+)-genipin as the chiral starting material. The reported synthetic approach is characterized with the orchestrated cascade annulation between tryptamine and the highly functionalized dialdehyde precursor to rapidly introduce the unique 6/5/6/7/6-fused pentacyclic skeleton and the functional group ketone at C19 in a convergent manner. The successful implementation of the transannular oxidative cyclization at C3 for the bridged oxazolidine formation in the late-stage synthetic campaign ensured the final total synthesis of this molecule.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":null,"pages":null},"PeriodicalIF":5.4,"publicationDate":"2024-07-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141566053","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 Ligand-assisted Manganese-enabled Direct C-H Difluoromethylation of Arenes 配体辅助的锰催化烯的直接 C-H 二氟甲基化反应
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2024-07-10 DOI: 10.1039/d4qo00786g
Kehan Zhou, Shuang Xia, Yuheng Xiao, Zhi-Bin Huang, Jingyu Zhang, Yingsheng Zhao
{"title":"A Ligand-assisted Manganese-enabled Direct C-H Difluoromethylation of Arenes","authors":"Kehan Zhou, Shuang Xia, Yuheng Xiao, Zhi-Bin Huang, Jingyu Zhang, Yingsheng Zhao","doi":"10.1039/d4qo00786g","DOIUrl":"https://doi.org/10.1039/d4qo00786g","url":null,"abstract":"The incorporation of a difluoromethyl group within an aromatic ring is highly desirable. However, studies based on direct C-H difluromethylation reactions of arenes are sparsely reported in literature. Therefore, in this work a light-induced Mn-enabled Dave-phos-promoted direct C-H difluoromethylation reaction of general arenes has been explored in detail with the variable ArSO2CF2Br as the coupling partner under mild conditions. Various arenes and bioactive molecules were all well tolerated, producing the resultant products in moderate to high yields. Preliminary mechanistic studies suggested that Mn2(CO)10 could not only mediate the halogen-atom transfer process (XAT) to provide active ArSO2CF2• radicals but was also able to coordinate with the arenes through -complexation to activate the aromatic ring. This facilitated the reaction between the aromatic ring and the ArSO2CF2• radical.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":null,"pages":null},"PeriodicalIF":5.4,"publicationDate":"2024-07-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141566050","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
Zwitterion Detection with a Fluorescent Squaramide Cryptand: A Study in Size-Dependent Salt Recognition and Sensing 用荧光水杨酰胺隐体检测齐聚物:尺寸依赖性盐识别和传感研究
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2024-07-09 DOI: 10.1039/d4qo01136h
Marta Zaleskaya, Marcin Wilczek, Łukasz Dobrzycki, Jan Romanski
{"title":"Zwitterion Detection with a Fluorescent Squaramide Cryptand: A Study in Size-Dependent Salt Recognition and Sensing","authors":"Marta Zaleskaya, Marcin Wilczek, Łukasz Dobrzycki, Jan Romanski","doi":"10.1039/d4qo01136h","DOIUrl":"https://doi.org/10.1039/d4qo01136h","url":null,"abstract":"We report the synthesis of a novel squaramide based cryptand incorporating both anion and cation binding domains, and a fluorescent reporter designed to monitor the complexation process. The preorganization of the binding domains in the cryptand structure favored stronger binding of anions as compared with the open chain counterpart. X-ray structural analysis of the cryptand complex with ion pairs confirmed the interaction of ions with binding sites in the solid state. Employing a ball milling technique resolved solubility issues, facilitating the study of interactions between the cryptand and salts. We found that the cryptand exhibits stronger binding affinity for carboxylates than for chloride anions. This property, coupled with the closed structure of the cryptand, was utilized for the selective recognition of zwitterions differing in chain length. Mechanochemical methods allow for qualititative binding of amino acids within the receptor cavity. Fluorescence studies revealed the behavior of cryptand 1 as a sensor enabling the selective recognition of zwitterions, a capability not observed in the sensor with an open structure.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":null,"pages":null},"PeriodicalIF":5.4,"publicationDate":"2024-07-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141561597","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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