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Room-temperature nickel-catalyzed borylation/cyclization synthesis of benzoxaboroles and benzodiazaborines 室温镍催化硼化/环化合成苯并恶硼和苯并二氮杂硼
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-06-13 DOI: 10.1039/d5qo00728c
Xiaoning Yang, Shuyan Wu, Jiayi Wang, Yanqing Peng, Gonghua Song
{"title":"Room-temperature nickel-catalyzed borylation/cyclization synthesis of benzoxaboroles and benzodiazaborines","authors":"Xiaoning Yang, Shuyan Wu, Jiayi Wang, Yanqing Peng, Gonghua Song","doi":"10.1039/d5qo00728c","DOIUrl":"https://doi.org/10.1039/d5qo00728c","url":null,"abstract":"Benzoxaboroles and benzodiazaborines are pivotal in medicinal chemistry due to their unique biological activities and potential as therapeutic agents. Herein, we present a room-temperature, nickel-catalyzed borylation protocol for the efficient synthesis. Utilizing an inexpensive nickel catalyst system, this method provides a facile synthetic method for a wide range of target compounds. This cost-effective approach offers a sustainable alternative to traditional palladium-based methods, aligning with green chemistry principles by reducing energy input and enhancing reaction efficiency. In addition to expanding the range of boronic acid derivatives, the developed methodology holds significant promise for advancing applications in drug discovery.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"1 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-06-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144278650","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
Bicyclic 2-Pyridone, with Fused Heterocyclic Rings, a Facile Core for Pure Type I Photosensitizers 具有融合杂环的双环2-吡啶酮，纯I型光敏剂的易溶核心
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-06-12 DOI: 10.1039/d5qo00684h
Zhicheng Ban, Ning Ma, Hui Tang, Xiaoyun Ran, Qian Zhou, Yahui Zhang, Zhouyu Wang, Xiao-Qi Yu
{"title":"Bicyclic 2-Pyridone, with Fused Heterocyclic Rings, a Facile Core for Pure Type I Photosensitizers","authors":"Zhicheng Ban, Ning Ma, Hui Tang, Xiaoyun Ran, Qian Zhou, Yahui Zhang, Zhouyu Wang, Xiao-Qi Yu","doi":"10.1039/d5qo00684h","DOIUrl":"https://doi.org/10.1039/d5qo00684h","url":null,"abstract":"Effectively improving the ability of electron transfer is the cornerstone of designing pure type I photosensitizers (PSs). At present, the bright strategies are to introduce the electron-rich structures to promote electron transfer capacity. Herein, we developed a novel core with fused heterocyclic ring (bicyclic 2-pyridone, BCP) based on which a series of excellent pure type I PSs can subsequently be constructed. BCP, with the fused heterocyclic rings, can act as an “electronic pool” for forming electron-rich environment. Electrochemical experiments and theoretical calculations prove that BCP has a more significant electron transfer phenomenon compared to the non-conjugated one. Based on BCP, the pure type I PSs core, triphenylamine (electron donor, D) was introduced to produce a molecule (BCP-TPA) with near infrared emission and high type I PDT efficiency by the typical D-π-D structure. BCP-TPA showed superior ability to produce pure type I ROS, which effectively inhibited tumor growth in in vivo experiments. This work provides a new core to synthesize pure type I PSs, combining fused heterocyclic rings to form electron-rich environment.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"22 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-06-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144268961","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(I)-Catalyzed Tandem C−N Coupling/Condensation Cyclization for the Synthesis of Benzothiadiazine 1‑Oxides 铜(I)催化串联C−N偶联/缩合环化合成苯并噻嗪1 -氧化物
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-06-11 DOI: 10.1039/d5qo00681c
Sihan Zhou, Qingle Zeng
{"title":"Copper(I)-Catalyzed Tandem C−N Coupling/Condensation Cyclization for the Synthesis of Benzothiadiazine 1‑Oxides","authors":"Sihan Zhou, Qingle Zeng","doi":"10.1039/d5qo00681c","DOIUrl":"https://doi.org/10.1039/d5qo00681c","url":null,"abstract":"A highly efficient and straightforward strategy for the synthesis of benzothiadiazine 1-oxides has been developed, involving copper(I)-catalyzed tandem C–N coupling/condensation cyclization of ortho-haloaryl organyl NH-sulfoximines and aromatic/aliphatic amidines. This protocol exhibits several notable advantages, including the absence of the requirement for an additional nitrogen source, a broad substrate scope, mild reaction conditions, and significant potential for application in the industrial production of benzothiadiazine 1-oxides.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"6 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-06-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144260761","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
Kinetic resolution of trifluoromethylated heterobenzhydrols via hydrogen-acceptor-free Ir-catalyzed heteroaryl-selective C−H silylation 通过无氢受体ir催化的异芳基选择性C - H硅基化动力学拆分三氟甲基化杂苯氢
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-06-11 DOI: 10.1039/d5qo00725a
Yoshihiko Yamamoto, Takeshi Yasui, Ryu Tadano
{"title":"Kinetic resolution of trifluoromethylated heterobenzhydrols via hydrogen-acceptor-free Ir-catalyzed heteroaryl-selective C−H silylation","authors":"Yoshihiko Yamamoto, Takeshi Yasui, Ryu Tadano","doi":"10.1039/d5qo00725a","DOIUrl":"https://doi.org/10.1039/d5qo00725a","url":null,"abstract":"Kinetic resolution of benzhydrols via intramolecular C−H silylation is an efficient method for the preparation of chiral benzhydrols. However, the previously reported methods required sterically demanding phenyl rings to achieve group-selective C−H silylation. Herein, we report the kinetic resolution of trifluoromethylated heterobenzhydrols, bearing both phenyl and thiophene rings, via heteroaryl-selective C−H silylation. We conducted computational studies on the factors influencing the enantioselectivity and heteroaryl selectivity.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"6 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-06-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144268909","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
Tandem reductive alkylation of quinolines to functionalized tetrahydroquinolines enabled by HFIP 用HFIP催化喹啉串联还原烷基化制功能化四氢喹啉
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-06-11 DOI: 10.1039/d5qo00519a
Animesh Das, Siddhartha Kumar Senapati, Tapashi Das
{"title":"Tandem reductive alkylation of quinolines to functionalized tetrahydroquinolines enabled by HFIP","authors":"Animesh Das, Siddhartha Kumar Senapati, Tapashi Das","doi":"10.1039/d5qo00519a","DOIUrl":"https://doi.org/10.1039/d5qo00519a","url":null,"abstract":"Hexafluoroisopropanol (HFIP)-mediated a one-pot tandem reduction of quinolines to tetrahydroquinolines followed by reductive alkylation by the aldehyde has been demonstrated through H-bonding network-enabled substrate activation. This step-economical synthetic approach is well suited for late-stage functionalization of complex bioactive molecules. The reaction is highly chemoselective and tolerates a wide range of reducible-sensitive functional groups. The current reductive N-alkylation approach was also successfully utilized to synthesize novel tricyclic oxazino-fused-tetrahydroquinoline/ benzoxazine compounds via tandem reductive cyclization of 1-aryl-2-(8-quinolinyloxy) ethanones and synthesis of Lilolidine derivatives through the reductive N-alkylation of quinoline followed by dehydration cyclization sequence. Scope of the reaction has been further extended to C-functionalized N-alkylated THQ derivatives in a one-pot by using para-quinone methides (p-QMs) or nitroolefins as alkylating precursors. The elucidation of the underlying mechanism was achieved through a combination of several control experiments, kinetic studies, and isotopic labelling experiments.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"64 2 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-06-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144260760","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
Negatively curved carbonyl-bridged triphenylamine 负弯曲羰基桥接三苯胺
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-06-11 DOI: 10.1039/d5qo00794a
Lin Wan, Yude Ji, Zikang Ma, Chengguo Yan, Weifan Wang, Gang Zhang
{"title":"Negatively curved carbonyl-bridged triphenylamine","authors":"Lin Wan, Yude Ji, Zikang Ma, Chengguo Yan, Weifan Wang, Gang Zhang","doi":"10.1039/d5qo00794a","DOIUrl":"https://doi.org/10.1039/d5qo00794a","url":null,"abstract":"The planar and positively curved carbonyl-bridged triphenylamine derivatives with five- and six-membered rings around the central nitrogen atom have been extensively studied. However, the incorporation of seven-membered ring to form negatively curved carbonyl-bridged triphenylamine derivatives is still scarce. Herein we report the synthesis of negatively curved carbonyl-bridged triphenylamine compound bearing double hexagonal rings and a heptagonal ring around the central nitrogen atom. The peripheral double bond of the heptagonal ring can be oxidized to generate adjacent diketone compound with room temperature phosphorescence. Naphthalene and quinoxaline units can be fused to the seven-membered ring to give the saddle-shaped derivatives, which can assemble with C60 in 1:1 ratio with different binding constants in toluene depending on the fused units.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"6 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-06-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144260600","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: Twisted organic TADF triads based on a diindolocarbazole donor for efficient photoisomerization of stilbene and photo-arylation of heteroarenes 更正：基于二吲哚咔唑供体的扭曲有机TADF三合体，用于二苯乙烯的高效光异构化和杂芳烃的光芳化
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-06-10 DOI: 10.1039/d5qo90048d
Sushil Sharma, Sanchita Sengupta
{"title":"Correction: Twisted organic TADF triads based on a diindolocarbazole donor for efficient photoisomerization of stilbene and photo-arylation of heteroarenes","authors":"Sushil Sharma, Sanchita Sengupta","doi":"10.1039/d5qo90048d","DOIUrl":"https://doi.org/10.1039/d5qo90048d","url":null,"abstract":"Correction for ‘Twisted organic TADF triads based on a diindolocarbazole donor for efficient photoisomerization of stilbene and photo-arylation of heteroarenes’ by Sushil Sharma <em>et al.</em>, <em>Org. Chem. Front.</em>, 2023, <strong>10</strong>, 6087–6095, https://doi.org/10.1039/D3QO01542D.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"215 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-06-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144252425","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
Retro-Mukaiyama Aldol reaction-driven silicon catalysis retromukaiyama Aldol反应驱动硅催化
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-06-09 DOI: 10.1039/d5qo00740b
Yongjing Dong, Yue Hu, Yiqing Wang, Liqun Jin, Yinjun Xie
{"title":"Retro-Mukaiyama Aldol reaction-driven silicon catalysis","authors":"Yongjing Dong, Yue Hu, Yiqing Wang, Liqun Jin, Yinjun Xie","doi":"10.1039/d5qo00740b","DOIUrl":"https://doi.org/10.1039/d5qo00740b","url":null,"abstract":"The use of silicon reagent as catalyst has long been an attractive yet challenging goal due to the difficulty of silicon catalyst regeneration. Herein, we report a novel silicon-catalyzed formal hydroformylation of alkynes with aldehydes to access α,β-unsaturated ketones with high efficiency under mild conditions. The success of this method relies on the innovative of retro-Mukaiyama aldol reaction (RMAR)-driven silyl transfer strategy, which enables efficient regeneration of silicon catalyst. Preliminary mechanistic studies reveal the evolution of the key silicon catalysts during this transformation. This protocol provides valuable insights for the design of new chemical transformations based on silicon catalysis.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"10 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-06-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144238261","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
HBF4-Mediated Direct Alcoholysis of Amides Under Mild Conditions 温和条件下hbf4介导的酰胺直接醇解
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-06-06 DOI: 10.1039/d5qo00603a
Shi-Zheng Liu, Wen-Heng Liu, Yaotai Deng, Qiang Li, Mingyu Dou, Yu Cui, Jianmin Dou
{"title":"HBF4-Mediated Direct Alcoholysis of Amides Under Mild Conditions","authors":"Shi-Zheng Liu, Wen-Heng Liu, Yaotai Deng, Qiang Li, Mingyu Dou, Yu Cui, Jianmin Dou","doi":"10.1039/d5qo00603a","DOIUrl":"https://doi.org/10.1039/d5qo00603a","url":null,"abstract":"A metal-free, HBF<small><sub>4</sub></small>-mediated alcoholysis of amides under relatively mild conditions is reported. This operationally simple process provides a new route to amide-ester bond conversion with excellent chemoselectivity. In particular, a wide range of primary, secondary and tertiary amides, including the challenging thioamides, can be esterified in very high yields. In addition, this transformation does not require the use of additional solvent, and many products can be obtained by washing with water.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"39 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-06-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144229280","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 Cascade Synthesis of Tricyclic Quinolin-2(1H)-ones from 1,7-Enynes and Hydroxylamines 钯催化1,7-炔和羟胺级联合成三环喹啉-2(1H)-酮
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-06-05 DOI: 10.1039/d5qo00697j
Jiajun Zhao, Xiaolong Wang, Yan Cao, Jun Ying
{"title":"Palladium-Catalyzed Cascade Synthesis of Tricyclic Quinolin-2(1H)-ones from 1,7-Enynes and Hydroxylamines","authors":"Jiajun Zhao, Xiaolong Wang, Yan Cao, Jun Ying","doi":"10.1039/d5qo00697j","DOIUrl":"https://doi.org/10.1039/d5qo00697j","url":null,"abstract":"A palladium-catalyzed cascade radical cyclization and C-H amination of 1,7-enynes with perfluoroalkyl iodides and hydroxylamine has been developed for the rapid construction of tricyclic quinolin-2(1H)-one scaffolds. The reaction proceeded smoothly to give a series of tricyclic quinolin-2(1H)-one derivatives in high yields. Notably, the late-stage modifications of various drugs were realized by using this method.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"16 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-06-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144219145","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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