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Hypervalent Iodine-mediated One-pot Synthesis of C3,6-Dithioquinolin-2-ones 高价碘介导的一锅法合成C3,6-二硫代喹啉-2-酮
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-04-09 DOI: 10.1039/d5qo00337g
Yukun Xie, Xiaodan Meng, Chenrui Liu, Xiaoxiang Zhang, Zhuan Zhang, Taoyuan Liang
{"title":"Hypervalent Iodine-mediated One-pot Synthesis of C3,6-Dithioquinolin-2-ones","authors":"Yukun Xie, Xiaodan Meng, Chenrui Liu, Xiaoxiang Zhang, Zhuan Zhang, Taoyuan Liang","doi":"10.1039/d5qo00337g","DOIUrl":"https://doi.org/10.1039/d5qo00337g","url":null,"abstract":"This study presents a transition-metal-free one-pot synthetic strategy for the efficient construction of C3,6-dithioquinolin-2-ones, which employs N-substituted tetrahydroquinolines and disulfides in a direct reaction, utilizing 2-iodoxybenzoic acid (IBX) as the oxidant and water as co-solvent to achieve regioselective oxidative desulfurization and functionalization of quinoline C–H bonds under mild conditions. In contrast to conventional approaches, this protocol eliminates the need for transition-metal catalysts (e.g., Pd, Ru) and directing groups, significantly reducing environmental risks associated with toxic reagents and lowering synthesis costs, and demonstrates high atom and step economy. Furthermore, the mixed solvent system (DCE/H₂O) reduces organic solvent consumption, while the broad substrate scope. Derivatization experiments confirm the straightforward conversion of products into functional molecules, offering a sustainable pathway for synthesizing complex heterocycles and providing a powerful means to expand diverse synthetic routes.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"21 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-04-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143813777","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
Correction: Transition-metal-free borylation of propargylic alcohols: structurally variable synthesis in ionic liquid medium 更正：丙炔醇的无过渡金属硼烷基化：离子液体介质中结构可变的合成方法
IF 4.6 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-04-09 DOI: 10.1039/D5QO90027A
Sangepu Bhavanarushi, Yin Xu, Imran Khan, Zhibin Luo, Bin Liu and Jimin Xie
{"title":"Correction: Transition-metal-free borylation of propargylic alcohols: structurally variable synthesis in ionic liquid medium","authors":"Sangepu Bhavanarushi, Yin Xu, Imran Khan, Zhibin Luo, Bin Liu and Jimin Xie","doi":"10.1039/D5QO90027A","DOIUrl":"10.1039/D5QO90027A","url":null,"abstract":"<p >Correction for ‘Transition-metal-free borylation of propargylic alcohols: structurally variable synthesis in ionic liquid medium’ by Sangepu Bhavanarushi <em>et al.</em>, <em>Org. Chem. Front.</em>, 2019, <strong>6</strong>, 1895–1899, https://doi.org/10.1039/C9QO00322C.</p>","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":" 9","pages":" 3143-3144"},"PeriodicalIF":4.6,"publicationDate":"2025-04-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.rsc.org/en/content/articlepdf/2025/qo/d5qo90027a?page=search","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143806576","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Nickel/Photo-Cocatalyzed Three-Component Silylarylation of Electron-Deficient Alkenes 镍/光共催化缺电子烯烃的三组分硅芳基化反应
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-04-08 DOI: 10.1039/d5qo00346f
Pei Fan, Xiao-Xue Huang
{"title":"Nickel/Photo-Cocatalyzed Three-Component Silylarylation of Electron-Deficient Alkenes","authors":"Pei Fan, Xiao-Xue Huang","doi":"10.1039/d5qo00346f","DOIUrl":"https://doi.org/10.1039/d5qo00346f","url":null,"abstract":"Herein we report a nickel/photo-cocatalyzed silylarylation of electron-deficient alkenes with aryl bromides and hydrosilanes, providing new access to a variety of β-silyl-α-aryl propionates with good functionality tolerance. Tetrabutylammonium decatungstate-mediated chemoselective radical Si-H activation via hydrogen atom transfer, sila-Giese addition, and nickel-mediated C‒C bond formation constitute the key elementary steps of this process.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"31 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-04-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143797668","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
Photo and Earth-Abundant Metal Dual Catalysis in Organic Synthesis 有机合成中的光与富土金属双重催化
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-04-08 DOI: 10.1039/d5qo00102a
Guannan Li, Tongtong Li, Lifeng Luo, Yan Tan, Zhan Lu
{"title":"Photo and Earth-Abundant Metal Dual Catalysis in Organic Synthesis","authors":"Guannan Li, Tongtong Li, Lifeng Luo, Yan Tan, Zhan Lu","doi":"10.1039/d5qo00102a","DOIUrl":"https://doi.org/10.1039/d5qo00102a","url":null,"abstract":"This review summarizes the latest research progress on photocatalytic reactions involving typical metal catalysts Sc, Ti, V, Cr, Mn, Fe, Co, Ni, and Cu, and mainly focuses on the role of metals and light in the reaction process.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"63 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-04-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143797665","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 norbornene derivatives-mediated ortho-C−H silylation: access to divergent silicon-containing carbazoles 钯（II）催化降冰片烯衍生物介导的正位c−H硅基化：获得发散的含硅咔唑
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-04-07 DOI: 10.1039/d5qo00409h
Wenguang Li, Jing Tao, Heyun Sheng, Man Cao, Ming Chen, Wenchao Gao, Xu Zhang, Wentao Li, Yongqi Yu, Ting Li
{"title":"Palladium(II)-catalyzed norbornene derivatives-mediated ortho-C−H silylation: access to divergent silicon-containing carbazoles","authors":"Wenguang Li, Jing Tao, Heyun Sheng, Man Cao, Ming Chen, Wenchao Gao, Xu Zhang, Wentao Li, Yongqi Yu, Ting Li","doi":"10.1039/d5qo00409h","DOIUrl":"https://doi.org/10.1039/d5qo00409h","url":null,"abstract":"A palladium(II)-catalyzed norbornene derivatives-mediated selective <em>ortho</em>-C−H silylation of free NH-carbazoles has been developed for the synthesis of arylsilanes. Such a conversion provides access to a range of arylsilanes with exclusive selectivity using norbornene (NBE) derivatives as the transient directing mediators. The kinetic experiments show that C–H activation is the rate determining step for the conversion. Notably, a six-membered palladacycle intermediate was involved in this case.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"28 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-04-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143790100","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 Photoredox Catalyzed Kornblum Oxidation Reactions for Unnatural Amino Acids Synthesis† 光氧化还原催化合成非天然氨基酸的Kornblum氧化反应
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-04-07 DOI: 10.1039/d4qo02281e
Li Fan Deng, Mingxing Huang, Weichen Wang, Shiyang Xu, Xiang Pu, Rong Tian, Yingwei Wang
{"title":"A Photoredox Catalyzed Kornblum Oxidation Reactions for Unnatural Amino Acids Synthesis†","authors":"Li Fan Deng, Mingxing Huang, Weichen Wang, Shiyang Xu, Xiang Pu, Rong Tian, Yingwei Wang","doi":"10.1039/d4qo02281e","DOIUrl":"https://doi.org/10.1039/d4qo02281e","url":null,"abstract":"Unnatural amino acids are important building blocks in organic synthesis and drug discovery. They are also frequently inte-grated into peptides or proteins for biological studies. However, the direct and simplified synthesis of UAAs remains a great challenge. At the same time, vast known peptide modifications are based on carbon-heteroatom bonds. There are no general methods for peptide modifications via the construction of C–C bonds. To address this challenge, herein we propose styrene could serve as an alternative alkene substrate for the synthesis of UAAs. Leveraging the p-π conjugation-assisted effect to generate intermediates to build C–C bond. This protocol has obvious advantages such as good functional group tolerance, biocompatible reaction conditions, and retained stereochemistry. This strategy was successfully utilized for the synthesis of unnatural amino acids and direct modifications of peptides.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"21 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-04-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143797666","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 three-component 1, 2-boroarylation and carbopyridylation of alkene 光催化烯烃的三组分1,2 -硼芳基化和碳吡啶化
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-04-07 DOI: 10.1039/d5qo00380f
Jia Cao, Baobao Ji, Zhixiang Wang, Ruijuan Wang, Liuzhou Gao
{"title":"Photocatalytic three-component 1, 2-boroarylation and carbopyridylation of alkene","authors":"Jia Cao, Baobao Ji, Zhixiang Wang, Ruijuan Wang, Liuzhou Gao","doi":"10.1039/d5qo00380f","DOIUrl":"https://doi.org/10.1039/d5qo00380f","url":null,"abstract":"Herein we present photocatalytic three-component 1,2-boroarylation of alkene with readily available alkene, bis(pinacolato)diboron, and (hetero)aryl nitriles in the presence of base and photocatalyst, providing diverse boryl-enriched 1,1-diarylalkane compounds. Alkylboronic pinacol esters are also suitable substrates to give the corresponding carbopyridylation products. Control experiments and DFT calculations supported our proposed photoinduced generations of a boryl unit and aryl nitrile radical anion, which sequential coupled to alkene. This protocol exhibits mild reaction conditions, good functional tolerances and one-pot procedure, complementing the transition metal-catalyzed coupling reaction.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"37 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-04-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143790095","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
Metal and photocatalyst-free alkylboration of [1.1.1]propellane enabled by red-light-induced electron transfer 通过红光诱导的电子转移实现 [1.1.1]propellane 的无金属和无光催化剂烷基硼化
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-04-04 DOI: 10.1039/d5qo00357a
Yuying Wang, Jianyang Dong, Yulin Xiao, Zhilin Wang, Weilin Wu, Dong Xue
{"title":"Metal and photocatalyst-free alkylboration of [1.1.1]propellane enabled by red-light-induced electron transfer","authors":"Yuying Wang, Jianyang Dong, Yulin Xiao, Zhilin Wang, Weilin Wu, Dong Xue","doi":"10.1039/d5qo00357a","DOIUrl":"https://doi.org/10.1039/d5qo00357a","url":null,"abstract":"Highly strained 1,3-disubstituted bicyclo[1.1.1]pentanes (BCPs) have emerged as bioisosteres of para-disubstituted benzene rings because of the ability of the former to impart valuable pharmacokinetic properties. However, challenges such as the lack of convenient and green access to useful BCP building blocks continue to hinder early-stage discovery research. Herein, we report a metal and photocatalyst-free method for deaminative borylation of [1.1.1]propellane for the synthesis of BCP boronates. This method involves the generation of alkyl or α-ester alkyl radicals via red-light-induced formation of a ternary electron donor–acceptor complex between a Katritzky salt, Cs2CO3, and B2pin2. Selective addition of the radicals to [1.1.1]propellane produces BCP radicals that undergo polarity-matched addition to B2pin2, leading to BCP difunctionalization. The method, which does not require metals or photocatalysts, allows for direct construction of alkyl species from readily available amines and α-amino acids and concurrent introduction of synthetically versatile pinacol boronate (Bpin) groups onto the BCP substructure. We demonstrate the synthetic utility of our method through several important transformations of the Bpin and hydroxyl functional groups of the products, including photoinduced cross-coupling reactions of BCP-BF3K derived from BCP-Bpin.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"7 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-04-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143775779","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
Garynthone A–I, PPAPs with diverse skeletons isolated from Garcinia yunnanensis and their immunosuppressive activity Garynthone A-I、云南藤黄不同骨架PPAPs及其免疫抑制活性研究
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-04-04 DOI: 10.1039/d5qo00414d
Zifeng Guo, Pengxue Ji, Shengnan Yang, Zhiyuan Li, Yongbo Yu, Jingming Jia, Anhua Wang
{"title":"Garynthone A–I, PPAPs with diverse skeletons isolated from Garcinia yunnanensis and their immunosuppressive activity","authors":"Zifeng Guo, Pengxue Ji, Shengnan Yang, Zhiyuan Li, Yongbo Yu, Jingming Jia, Anhua Wang","doi":"10.1039/d5qo00414d","DOIUrl":"https://doi.org/10.1039/d5qo00414d","url":null,"abstract":"This study reports the isolation and structural characterization of 17 PPAPs from <em>G. yunnanensis</em>, including the novel Garynthone A (<strong>1</strong>) featuring an unprecedented 5-oxapentacyclo [7,3,1,1<small><sup>4,7</sup></small>,1<small><sup>6,11</sup></small>,0<small><sup>1,6</sup></small>] pentadecane skeleton, along with eight previously undescribed PPAPs (<strong>2–9</strong>). NMR data analysis, coupling constants analysis, quantum calculations, modified mosher's method, X-ray single-crystal crystallography, ECD spectra, computer-assisted structure elucidation (CASE), and DP5/DP4 probability analyses were employed to characterize their structures and revise the structure of garcoblone E (<strong>10</strong>). Compounds (+)-<strong>2</strong>, <strong>3</strong>, (+)-<strong>4</strong>, <strong>5</strong>, (±)-<strong>6</strong>, (±)-<strong>7</strong>, <strong>9</strong>, <strong>14</strong>, <strong>16</strong>, and <strong>17</strong> exhibited moderate inhibition of T-cell proliferation, with IC<small><sub>50</sub></small> values ranging from 2.02 to 19.41 μM.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"27 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-04-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143775781","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
Photo-induced energy transfer mediated O2-initiated deboronative generation of alkyl radicals from alkyl boronic acids and its application in radical Smiles rearrangement 光诱导能量转移介导o2引发的烷基硼酸自由基的波解生成及其在自由基Smiles重排中的应用
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-04-04 DOI: 10.1039/d5qo00323g
Jinpeng Wu, Yongsheng Tian, Xue Zhao, Shuai Liu, Liang Xu, Huanhuan Song
{"title":"Photo-induced energy transfer mediated O2-initiated deboronative generation of alkyl radicals from alkyl boronic acids and its application in radical Smiles rearrangement","authors":"Jinpeng Wu, Yongsheng Tian, Xue Zhao, Shuai Liu, Liang Xu, Huanhuan Song","doi":"10.1039/d5qo00323g","DOIUrl":"https://doi.org/10.1039/d5qo00323g","url":null,"abstract":"A visible-light-induced, energy-transfer mechanism for O2-initiated deboronative generation of alkyl radical approaches from alkylboronic acids and guided to a Smiles rearrangement reaction has been developed. This protocol utilizes tetracoordinate boron (AQDAB) as an energy transfer photosensitizer and features mild conditions, a broad substrate scope, and excellent functional group compatibility, providing a facile method for synthesizing all-carbon quaternary center amide compounds.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"141 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-04-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143775777","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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