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Palladium-catalyzed dearomative Heck/[4 + 3] decarboxylative cyclization of indoles with α-oxocarboxylic acids via C−H activation
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2024-12-19 DOI: 10.1039/d4qo02024c
Liwei Zhou, Pengyang Jing, Wenbo Deng, Shuyi Guo, Yun Liang, Yuan Yang
{"title":"Palladium-catalyzed dearomative Heck/[4 + 3] decarboxylative cyclization of indoles with α-oxocarboxylic acids via C−H activation","authors":"Liwei Zhou, Pengyang Jing, Wenbo Deng, Shuyi Guo, Yun Liang, Yuan Yang","doi":"10.1039/d4qo02024c","DOIUrl":"https://doi.org/10.1039/d4qo02024c","url":null,"abstract":"Herein, we report a novel palladium-catalyzed dearomative Heck/[4 + 3] decarboxylative cyclization of C2-tethered indoles with α-oxocarboxylic acids via C−H activation. In this reaction, dearomatization of C2-tethered indoles occurs via a Heck reaction pathway, leading to the formation of the alkyl-Pd(II) species. Subsequently, this species undergoes C−H activation, rather than the typical nucleophilic trapping or β−H elimination, to generate C,C-palladacycles, which are then captured by α-oxocarboxylic acids to afford hexacyclic and octocyclic fused indolines containing a seven-membered ring.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"36 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-12-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142849705","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
Ball-milling and piezoelectric materials enabled radical trifluoromethylation of enamides and acrylamides
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2024-12-19 DOI: 10.1039/d4qo01911c
Vitalii Solomin, Matthias Liard, Philippe Jubault, Thomas Castanheiro
{"title":"Ball-milling and piezoelectric materials enabled radical trifluoromethylation of enamides and acrylamides","authors":"Vitalii Solomin, Matthias Liard, Philippe Jubault, Thomas Castanheiro","doi":"10.1039/d4qo01911c","DOIUrl":"https://doi.org/10.1039/d4qo01911c","url":null,"abstract":"A mechanochemical radical direct C(sp2)-H trifluoromethylation of enamide derivatives was developed using Togni II reagent. Under a mechanochemical compression, application of 0.5 to 1.0 equivalent of piezoelectric materials enabled the solid-state formation of the key CF3 radical intermediate under mild and sustainable conditions. Catalytic amount of piezoelectric material proved to be just as efficient. The protocol showed a general efficiency and tolerance to multiple functional groups accessing trifluoromethylated enamides with up to 88% yield with a full stereoselectivity. The reaction conditions were applied to acrylamide substrates enabling trifluoromethylated oxindole derivatives synthesis through a radical cascade cyclization initiated from CF3 radical addition on electron-poor C-C double bonds. Radical quenching experiments highlighted a radical mechanism, and control experiments showcased the crucial need of piezoelectric materials/ball-milling system.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"31 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-12-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142858052","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
Bipolarsterol A, a steroid with an unprecedented 6/5/6/5 carbon skeleton from the phytopathogenic fungus Bipolaris oryzae
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2024-12-19 DOI: 10.1039/d4qo02057j
Meijia Zheng, Xiaotian Zhang, Xinran Zhang, Yingjie Liu, Qin Li, Lidan Mao, Weiguang Sun, Chunmei Chen, Yonghui Zhang, Hucheng Zhu
{"title":"Bipolarsterol A, a steroid with an unprecedented 6/5/6/5 carbon skeleton from the phytopathogenic fungus Bipolaris oryzae","authors":"Meijia Zheng, Xiaotian Zhang, Xinran Zhang, Yingjie Liu, Qin Li, Lidan Mao, Weiguang Sun, Chunmei Chen, Yonghui Zhang, Hucheng Zhu","doi":"10.1039/d4qo02057j","DOIUrl":"https://doi.org/10.1039/d4qo02057j","url":null,"abstract":"Bipolarsterols A−H (<strong>1</strong>−<strong>8</strong>), eight undescribed steroids were isolated from <em>Bipolaris oryzae</em>, along with nine known congeners. Their structures and absolute configurations were elucidated by comprehensive spectroscopic techniques, NMR and ECD calculations. Compound <strong>1</strong> presents the first example of a 19(l0→5)-abeo-7(8→9)-abeo-ergostane, featuring an unusual spiro[4.5]decan-6-one system, and compound <strong>2</strong> is a new member of the rare steroid-phenylpropanoid hybrid. Compound <strong>5</strong> showed remarkable cytotoxicity against HT29 cells with an IC<small><sub>50</sub></small> value of 5.8 <em>μ</em>M. Compound <strong>8</strong> showed significant inhibitory effect on NO production in RAW264.7 with an IC<small><sub>50</sub></small> value of 2.7 <em>μ</em>M, through the inhibition of iNOS levels at the transcription and protein levels as well as the NF-<em>κ</em>B pathway.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"271 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-12-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142849829","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
Organocatalytic Enantioselective [2 + 2] Cycloadditions towards Chiral Fused -Trifluoromethyl Azetidines
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2024-12-19 DOI: 10.1039/d4qo01942c
Song Zhang, Xingjie Luo, Si-Qiang Fang, Jia-Hong Wu, Jianke Pan, Zhipeng Xu, Tianli Wang
{"title":"Organocatalytic Enantioselective [2 + 2] Cycloadditions towards Chiral Fused -Trifluoromethyl Azetidines","authors":"Song Zhang, Xingjie Luo, Si-Qiang Fang, Jia-Hong Wu, Jianke Pan, Zhipeng Xu, Tianli Wang","doi":"10.1039/d4qo01942c","DOIUrl":"https://doi.org/10.1039/d4qo01942c","url":null,"abstract":"Access to relatively high energy azetidines in enantioenriched form via a function- and diversity-oriented approach is highly desired in the field of drug-discovery. Although the demands for α-trifluoromethyl azetidines with great biological potential exist, effective strategies for catalytic asymmetric synthesis of these chemical entities with structural diversity remain elusive. To conquer this frontier, we, herein, report the development of a building block protocol for the facile assembly of enantioenriched α-trifluoromethyl azetidines via peptide-mimic phosphonium salt-catalyzed asymmetric [2 + 2] cycloadditions of tethered trifluoromethyl ketimines and allenes. Of note, this methodology could allow for the enantioselective synthesis of a diverse set of six-membered ring-fused α-trifluoromethyl azetidines bearing two densely functionalized carbon stereocenters in high yields with excellent diastereo- and enantioselectivities. Besides the fundamental appeal of this strategy, scale-up experiment and representative transformations could engender its prompt application in synthetic chemistry.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"53 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-12-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142849704","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
From conventional to dual Co/photoredox mediated reductive coupling of alkynes and alkenes
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2024-12-19 DOI: 10.1039/d4qo02143f
Balázs Tóth, Stephanie Grace Elizabeth Amos, Arjan Willem Kleij
{"title":"From conventional to dual Co/photoredox mediated reductive coupling of alkynes and alkenes","authors":"Balázs Tóth, Stephanie Grace Elizabeth Amos, Arjan Willem Kleij","doi":"10.1039/d4qo02143f","DOIUrl":"https://doi.org/10.1039/d4qo02143f","url":null,"abstract":"Metal-catalyzed reductive coupling reactions between alkenes and alkynes are a long-standing tradition as a way to create complex unsaturated building blocks of value in organic synthesis ventures. Here, we review the general synthetic approaches realized under Co-catalysis utilizing chemical reductants, albeit with some limitations in scope and user-friendliness. A more recent advancement shows that these reductive ene-yne coupling reactions can also be accommodated by photoredox catalysis marking a stepping stone in the area, and creating new incentives for this kind of carbon-carbon bond formation and beyond.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"27 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-12-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142849701","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
Visible-light-induced dehydrogenation of dihydroquinolinones via the combination of energy transfer and hydrogen atom transfers
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2024-12-19 DOI: 10.1039/d4qo01902d
Jin Feng, Hanguang Tang, Hao Guo, Aishun Ding
{"title":"Visible-light-induced dehydrogenation of dihydroquinolinones via the combination of energy transfer and hydrogen atom transfers","authors":"Jin Feng, Hanguang Tang, Hao Guo, Aishun Ding","doi":"10.1039/d4qo01902d","DOIUrl":"https://doi.org/10.1039/d4qo01902d","url":null,"abstract":"A visible-light-induced dehydrogenation of dihydroquinolinones was developed using the photocatalyst thioxanthone (TX) and oxidant <em>tert</em>-butyl benzoperoxoate. Various quinolinones, which constitute significant structural skeletons in organic and biological chemistry, were produced through a photocatalytic process involving energy transfer (EnT) and subsequent hydrogen atom transfers (HATs). This approach, involving a completely metal-free dehydrogenation process carried out under mild conditions, further extends the applications of TX in the sphere of photo-dehydrogenation.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"94 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-12-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142849703","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
Enantioselective Synthesis of α-Chiral Sulfonates through Palladium-Catalyzed Tsuji-Trost Sulfonylation with Sulfur Dioxide
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2024-12-18 DOI: 10.1039/d4qo01887g
Xiaochun He, Fei Zhou, Qingqing Wang, Xiaohong Wang, Zhiqian Chang, Xuemei Zhang, Zhong Lian
{"title":"Enantioselective Synthesis of α-Chiral Sulfonates through Palladium-Catalyzed Tsuji-Trost Sulfonylation with Sulfur Dioxide","authors":"Xiaochun He, Fei Zhou, Qingqing Wang, Xiaohong Wang, Zhiqian Chang, Xuemei Zhang, Zhong Lian","doi":"10.1039/d4qo01887g","DOIUrl":"https://doi.org/10.1039/d4qo01887g","url":null,"abstract":"α-Chiral sulfonates have remained largely uncharted territory, primarily due to the intrinsic difficulties associated with achieving stereocontrol. In this study, we present an innovative three-component palladium-catalyzed asymmetric Tsuji-Trost sulfonylation protocol, which introduces a novel strategy for the synthesis of enantiomerically enriched α-chiral sulfonates, utilizing S(VI) complexes as intermediates. This method is versatile, applicable to a diverse array of allylic acetates and alcohols, thereby allowing for the efficient synthesis of α-chiral sulfonates with high yields, exceptional regio- and enantioselectivities (up to 99% ee). In conclusion, this strategy offers a practical and efficient route for the generation of chiral α-substituted linear allylic sulfonates.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"271 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-12-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142849706","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
Synthesis of Biological Studies of 3-Trideuteromethylated Chromones and their Heteroatom Analogues
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2024-12-18 DOI: 10.1039/d4qo02081b
Kaiyue Yang, Dongke Zhang, Ce Yang, Xueyan Yang, Jiaxin He, Haofeng Shi, Zichuan Liu, Yunfei Du
{"title":"Synthesis of Biological Studies of 3-Trideuteromethylated Chromones and their Heteroatom Analogues","authors":"Kaiyue Yang, Dongke Zhang, Ce Yang, Xueyan Yang, Jiaxin He, Haofeng Shi, Zichuan Liu, Yunfei Du","doi":"10.1039/d4qo02081b","DOIUrl":"https://doi.org/10.1039/d4qo02081b","url":null,"abstract":"The bioactive trideuteromethylated chromones and their heteroatom analogues were synthesized via trideuteromethylation of chromones and their heteroatom analogues by utilizing Fenton's reagent system with d6-DMSO as the “CD3” source. Mechanistically, it was postulated that the hydroxyl radical generated from Fenton's reagent system first reacted with d6-DMSO to give the electrophilic trideuteromethyl radical, which underwent radical substitution with chromones and their heteroatom analogues to give the title products. The obtained trideuteromethylated compounds were subjected to biological studies and the results revealed that this class of trideuteromethylated chromones and their heteroatom analogues exhibit good to excellent in vitro anti-lung carcinoma and anti-hepatoma activities.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"14 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-12-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142841637","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
Acetic acid-catalyzed synthesis of 1,5-disubstituted 1,2,3-triazoles under azide-free conditions
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2024-12-18 DOI: 10.1039/d4qo02118e
Jiuling Li, Xinyu Jia, Qiangguo Yang, Jiakang Guo, Qianhui Ren, Taichen Liu, Kai Wei, Zheng-Hui Kang
{"title":"Acetic acid-catalyzed synthesis of 1,5-disubstituted 1,2,3-triazoles under azide-free conditions","authors":"Jiuling Li, Xinyu Jia, Qiangguo Yang, Jiakang Guo, Qianhui Ren, Taichen Liu, Kai Wei, Zheng-Hui Kang","doi":"10.1039/d4qo02118e","DOIUrl":"https://doi.org/10.1039/d4qo02118e","url":null,"abstract":"An environmental-friendly and safe method has been developed to synthesize 1,5-disubstituted 1,2,3-triazoles containing difluoromethyl fragments, which can be obtained from readily available 2,2-difluoroarylethylamines under azide-free conditions. The classic conversion mode of acetic acid with tert-butyl nitrite is the critical factor in the reaction, allowing the diazo species in-situ generated to immediately react with the raw materials to give the desired products in good yields. The mild reaction conditions and convenient operations not only indicate such approach providing an attractive alternative method for the synthesis of polysubstituted 1,2,3-triazoles, but also further promote the applications of 2,2-difluoroarylethylamines in organic synthesis.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"69 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-12-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142841639","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
Solvent-controlled C2/C3-regioselective ring-opening/coupling of aziridines with amines and CS2: synthesis of 2-aminoethyl dithiocarbamates
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2024-12-18 DOI: 10.1039/d4qo02148g
Wenxue Li, Xueying Yang, Man Miao, Fengkai Sun, Hui Yuan, Xiaobing Lan, Jianqiang Yu, Jian Zhang, Zhenyu An
{"title":"Solvent-controlled C2/C3-regioselective ring-opening/coupling of aziridines with amines and CS2: synthesis of 2-aminoethyl dithiocarbamates","authors":"Wenxue Li, Xueying Yang, Man Miao, Fengkai Sun, Hui Yuan, Xiaobing Lan, Jianqiang Yu, Jian Zhang, Zhenyu An","doi":"10.1039/d4qo02148g","DOIUrl":"https://doi.org/10.1039/d4qo02148g","url":null,"abstract":"This study presents a solvent-controlled C2/C3-regioselective ring-opening/coupling of aziridines with amines and CS2, yielding two distinct types of 2-aminoethyl dithiocarbamates without the need for additives or non-green activation strategy. Featuring excellent atom economy, low-cost starting materials, broad substrate scope, and compatibility with clinically relevant molecules, this reaction is both efficient and sustainable for practical application. Control experiments and DFT calculations reveal that hydrogen bonding between solvents and aziridines directs selectivity by modulating orbital distributions, clarifying the selective reaction pathways.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"24 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-12-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142841643","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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