Organic Chemistry Frontiers最新文献_第3页

Diverse C(sp3)–H functionalizations through electrochemical benzylic oxygenation 不同的C(sp3) -H通过电化学苯氧化功能化

IF 5.4 1区化学

Organic Chemistry Frontiers Pub Date : 2025-01-16 DOI: 10.1039/d4qo02022g

Yan He, Tian-Sheng Chen, Xuesen Fan, Hai-Chao Xu

{"title":"Diverse C(sp3)–H functionalizations through electrochemical benzylic oxygenation","authors":"Yan He, Tian-Sheng Chen, Xuesen Fan, Hai-Chao Xu","doi":"10.1039/d4qo02022g","DOIUrl":"https://doi.org/10.1039/d4qo02022g","url":null,"abstract":"Despite significant advances in C(sp3)–H bond functionalization, the development of methods that are site-selective and capable of diverse bond formation remains a challenge. In addition, the preparation of olefins from aliphatics through cleavage of vicinal C(sp3)–H bonds remains difficult due to a lack of stereoselectivity and over-oxidation. To address these challenges, we have developed a transition metal catalyst- and external oxidant-free electrochemical C(sp3)–H oxygenation platform that enables highly stereoselective synthesis of aryl alkenes and diverse benzylic functionalizations to form various C–C and C–heteroatom bonds. This method involves site-selective benzylic C(sp3)–H trifluoroacetoxylation followed by elimination or substitution with diverse carbon- or heteroatom-based nucleophiles to form functionalized products. The utility of this protocol is further demonstrated by the desaturation of methyl dehydroabietate at the decagram scale and transformations of the resulting alkene. This study provides a platform for the diversity-oriented functionalization of both simple alkyl arenes and complex molecules.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"23 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-01-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142986061","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}

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Synthesis of Antimicrobial Active 9,10-Phenanthrenequinones by Carbene Organocatalytic Tandem Reactions 用卡宾有机催化串联反应合成具有抗菌活性的9,10-菲醌

IF 5.4 1区化学

Organic Chemistry Frontiers Pub Date : 2025-01-15 DOI: 10.1039/d4qo02193b

Yaoluo Hu, Ya Hong, Yuting Zheng, Yi Huang, Jixiang Chen, Xingxing Wu

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Recent advances in enantioselective construction of C–N bonds involving radical intermediate 含自由基中间体的C-N键对映选择性构建研究进展

IF 5.4 1区化学

Organic Chemistry Frontiers Pub Date : 2025-01-14 DOI: 10.1039/d4qo02268h

Jiaqiong Sun, Guangfan Zheng, Ge Zhang, Yan Li, Qian Zhang

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Recent Advances in Catalytic Asymmetric Reactions of Morita–Baylis–Hillman adducts Morita-Baylis-Hillman加合物催化不对称反应的研究进展

IF 5.4 1区化学

Organic Chemistry Frontiers Pub Date : 2025-01-14 DOI: 10.1039/d4qo02212b

Xu-Hong Duan, Hui-Ru Du, Yong-Xing Song

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Constructing less-conjugated olefins via unusual regioselective hydrogen atom transfer from acetals 通过不寻常的区域选择性从缩醛转移氢原子来构造共轭性较低的烯烃

IF 5.4 1区化学

Organic Chemistry Frontiers Pub Date : 2025-01-14 DOI: 10.1039/d4qo02099e

Zhaoshan Wang, Huiying Liu, Tian-Tian Liu, Qixiang Wang, Youhao Wei, Xiaoguang Bao, Xinxin Wu

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Influencing Optical and Charge Transport Properties by Controlling the Molecular Interactions of Merocyanine Thin Films 通过控制Merocyanine薄膜的分子相互作用影响其光学和电荷输运性质

IF 5.4 1区化学

Organic Chemistry Frontiers Pub Date : 2025-01-14 DOI: 10.1039/d4qo02088j

Klaus Meerholz, Lukas Böher, Philipp Weitkamp, Thorsten Limböck, Nora Gildemeister, Daniele Fazzi, Manuela Schiek, Ruth Bruker, Roland Schaefer, Dirk Hertel, Klas Lindfors

{"title":"Influencing Optical and Charge Transport Properties by Controlling the Molecular Interactions of Merocyanine Thin Films","authors":"Klaus Meerholz, Lukas Böher, Philipp Weitkamp, Thorsten Limböck, Nora Gildemeister, Daniele Fazzi, Manuela Schiek, Ruth Bruker, Roland Schaefer, Dirk Hertel, Klas Lindfors","doi":"10.1039/d4qo02088j","DOIUrl":"https://doi.org/10.1039/d4qo02088j","url":null,"abstract":"In amorphous organic semiconductors, charge transport typically takes place via slow hopping processes, but it is known that molecular aggregation can lead to enhanced exciton and charge transport through coupling of the transition dipole moments. In this work, we investigate the optical, morphological, and electronic properties of thin films of a merocyanine dye, which aggregates easily due to its dipolar character. Firstly, in spin-coated thin films the degree of aggregation of can be tuned by thermal annealing, leading to strong spectral shift alongside with strong Davydov splitting of > 800 meV. At the same time, the mobility increases by approximately three orders of magnitude. We combine variable angle spectroscopic ellipsometry and polarization-resolved absorption spectroscopy with density functional theory to demonstrate that the aggregated molecules are oriented in an upright, standing configuration (“tip-on”) relative to the substrate surface. This arrangement involves a co-facial orientation of the molecular pi-systems, which is advantageous for lateral charge transport. Secondly, by utilizing highly oriented pyrolytic graphite as an ordered substrate and low-rate vacuum deposition, we are able to template the growth of the merocyanine layer and to substantially improve the in-plane morphological order. By combining atomic force microscopy and photoluminescence microspectroscopy we observe large oriented domains of 100s of µm2 in size, emitting linearly polarized light, whereby maintaining the edge-on molecular arrangement. This promises a further significant enhancement of lateral charge carrier mobility.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"48 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-01-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142975556","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

Highly Selective Visible-Light-Induced Cascade Cyclization of Vinyl Sulfoxonium Ylides with Azides: A Novel Synthetic Approach to Trisubstituted Furans 高选择性可见光诱导叠氮基亚砜酰乙烯级联环化：合成三取代呋喃的新方法

IF 5.4 1区化学

Organic Chemistry Frontiers Pub Date : 2025-01-14 DOI: 10.1039/d4qo02195a

Jia-Huan Cui, Mei Tan, Jun Zhang, Yan He, Xingguang Li, Pei-Nian Liu

引用次数: 0

Three-step alkylaminomethylative α,β-difunctionalization of enones 烯酮的三步烷基胺甲基化α，β-二官能化

IF 5.4 1区化学

Organic Chemistry Frontiers Pub Date : 2025-01-13 DOI: 10.1039/d4qo02259a

Evgeny M. Buev, Vladimir Moshkin, Vyacheslav Sosnovskikh

{"title":"Three-step alkylaminomethylative α,β-difunctionalization of enones","authors":"Evgeny M. Buev, Vladimir Moshkin, Vyacheslav Sosnovskikh","doi":"10.1039/d4qo02259a","DOIUrl":"https://doi.org/10.1039/d4qo02259a","url":null,"abstract":"Aminomethylation of alkenes is a convenient methodology for the synthesis of aliphatic amines. This direction encompasses various methods, mainly allowing functionalization of the C=C bond of the molecule with the aminomethyl fragment at one atom and hydrogen or heteroatom at the other. This paper describes a three-step approach to the aminomethylation of electron-deficient alkenes, facilitating their α,β-difunctionalization and an introduction of two aminomethyl fragments into both positions of the alkene. The initial [3+2]-cycloaddition reaction of nonstabilized azomethine ylide at the C=C double bond of enones and subsequent treatment with alkyl halides lead to the formation of a key intermediate of the process – quaternary ammonium salt of 3-acylpyrrolidine. Heating of such salt in a polar solvent in the presence of a nucleophile results in a tandem Hofmann elimination/Michael addition to give 2-heteromethyl-4-aminobutan-1-ones with high diastereoselectivity and good to high overall yields. The proposed method benefits from inexpensive and available reagents, does not require noble metal catalysis and provides opportunities to apply a wide range of nucleophiles and alkyl halogenides, resulting in broad customization of the introduced heteromethyl moieties.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"74 6 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-01-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142975562","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

Benzofuranone-based spiropyrans: synthesis, temperature-dependent photochromic properties, and DFT calculations 苯并呋喃酮基螺吡喃：合成、温度依赖性光致变色性质和DFT计算

IF 5.4 1区化学

Organic Chemistry Frontiers Pub Date : 2025-01-13 DOI: 10.1039/d4qo02123a

Xincheng Zhou, Zhichao Chang, Yongchun Hu, Jianming Zhong, Jiaying Liao, Chunying Rong, Wang Zhou

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Photocatalyzed anti-Markovnikov addition of carboxylic acids to alkenes: ionic mechanism under radical conditions 光催化羧酸对烯烃的反马尔可夫尼科夫加成：自由基条件下的离子机理

IF 5.4 1区化学

Organic Chemistry Frontiers Pub Date : 2025-01-13 DOI: 10.1039/d4qo02280g

Dmitry L Lipilin, Mikhail O Zubkov, Mikhail Kosobokov, Alexander Dilman

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