Xuhong Zhao, Lian Ma, Meng Wang, Weishuang Li, Yaoyao Zhang, Bojie Li, Zhongpu Fang, Bo Xiong, Lei Zhu
Chiral organoboron compounds are essential intermediates in various significant reactions. However, there are still few efficient catalysts for their synthesis. This paper reports a novel catalytic material for chiral asymmetric boron conjugate addition reactions: mesoporous Cu₂O nanospheres (M‐Cu₂O). M‐Cu₂O is approximately 0.55 μm, exhibiting dense and uniformly distributed worm‐like pores. It features a specific surface area of 15.7 m²/g and an average pore size of 14.3 nm. Under the conditions of Toluene:H2O = 9:1, with a chiral ligand amount of 3.6 mol% and no additional base, it achieves a high yield (98% yield) and impressive enantioselectivity (98% ee ) for the template substrate chalcone using only 3.0 mol% of the catalyst. Notably, the catalyst can be easily recovered and maintains robust catalytic performance after seven cycles, yielding 92% and an ee value of 90%. This work presents a mild and effective method for synthesizing chiral boron compounds in an aqueous phase, significantly enhancing the application potential of mesoporous copper oxide nanospheres.
{"title":"Preparation of mesoporous Cu₂O nanospheres for green synthesis in the enantioselective boron conjugate addition of α,β‐unsaturated chiral compounds in aqueous phase","authors":"Xuhong Zhao, Lian Ma, Meng Wang, Weishuang Li, Yaoyao Zhang, Bojie Li, Zhongpu Fang, Bo Xiong, Lei Zhu","doi":"10.1002/adsc.202401501","DOIUrl":"https://doi.org/10.1002/adsc.202401501","url":null,"abstract":"Chiral organoboron compounds are essential intermediates in various significant reactions. However, there are still few efficient catalysts for their synthesis. This paper reports a novel catalytic material for chiral asymmetric boron conjugate addition reactions: mesoporous Cu₂O nanospheres (M‐Cu₂O). M‐Cu₂O is approximately 0.55 μm, exhibiting dense and uniformly distributed worm‐like pores. It features a specific surface area of 15.7 m²/g and an average pore size of 14.3 nm. Under the conditions of Toluene:H2O = 9:1, with a chiral ligand amount of 3.6 mol% and no additional base, it achieves a high yield (98% yield) and impressive enantioselectivity (98% ee ) for the template substrate chalcone using only 3.0 mol% of the catalyst. Notably, the catalyst can be easily recovered and maintains robust catalytic performance after seven cycles, yielding 92% and an ee value of 90%. This work presents a mild and effective method for synthesizing chiral boron compounds in an aqueous phase, significantly enhancing the application potential of mesoporous copper oxide nanospheres.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"6 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-01-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142937431","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
The burgeoning field of asymmetric catalysis has significantly advanced the construction of axially chiral compounds, recognized for their distinct three‐dimensional structures that are relevant in drug discovery, catalyst design and material science. Particularly, the atropisomeric aldehydes, characterized by a chiral axis and the presence of an aldehyde functionality, are of increasing value and interest in chemistry‐related domains, such as serving as privileged chiral catalysts for activation of amines. In recent years, elegant environmentally‐friendly metal‐free catalytic asymmetric methodologies based on de novo formation of (hetero)aromatic rings, dynamic kinetic resolution and desymmetrization have been established to build this fascinating class of atropisomers. In this review, we would like to highlight recent research progress on enantioselective synthesis of atropisomeric aldehydes by means of organocatalysis and biocatalysis, including their scopes, limitations, mechanisms, synthetic applications and provide some insights into future development. 1. Introduction 2. Ring Formation 3. Dynamic Kinetic Resolution 4. Desymmetrization 5. Conclusions and Outlook 6. References
{"title":"Research Progress on Organocatalytic Asymmetric Synthesis of Atropisomeric Aldehydes","authors":"Xing-Xing Liu, Zi-Rou Hu, Ming-Fei Duan, Dao-Juan Cheng","doi":"10.1002/adsc.202401553","DOIUrl":"https://doi.org/10.1002/adsc.202401553","url":null,"abstract":"The burgeoning field of asymmetric catalysis has significantly advanced the construction of axially chiral compounds, recognized for their distinct three‐dimensional structures that are relevant in drug discovery, catalyst design and material science. Particularly, the atropisomeric aldehydes, characterized by a chiral axis and the presence of an aldehyde functionality, are of increasing value and interest in chemistry‐related domains, such as serving as privileged chiral catalysts for activation of amines. In recent years, elegant environmentally‐friendly metal‐free catalytic asymmetric methodologies based on de novo formation of (hetero)aromatic rings, dynamic kinetic resolution and desymmetrization have been established to build this fascinating class of atropisomers. In this review, we would like to highlight recent research progress on enantioselective synthesis of atropisomeric aldehydes by means of organocatalysis and biocatalysis, including their scopes, limitations, mechanisms, synthetic applications and provide some insights into future development. 1. Introduction 2. Ring Formation 3. Dynamic Kinetic Resolution 4. Desymmetrization 5. Conclusions and Outlook 6. References","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"24 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-01-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142937430","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
A novel and efficient palladium‐catalyzed cyclization amination of propargylamines and 1,3‐dienes is reported for the first time, yielding a series of chloromethylene pyrrolidines with high efficiency and excellent selectivity. This method was successfully applied to the late‐stage modification of natural products and drug molecules, providing molecular backbones with potential applications. The reaction was shown to achieve regioselective modulation of the product molecules through the resonance between the solvent and allylpalladium. Additionally, the E‐form products were found to be thermodynamically stable.
{"title":"Palladium‐Catalyzed Cyclization Amination of Propargylamine and 1,3‐Dienes","authors":"Biao Yao, Wenfang Xiong, Wanqing Wu, Huanfeng Jiang","doi":"10.1002/adsc.202401464","DOIUrl":"https://doi.org/10.1002/adsc.202401464","url":null,"abstract":"A novel and efficient palladium‐catalyzed cyclization amination of propargylamines and 1,3‐dienes is reported for the first time, yielding a series of chloromethylene pyrrolidines with high efficiency and excellent selectivity. This method was successfully applied to the late‐stage modification of natural products and drug molecules, providing molecular backbones with potential applications. The reaction was shown to achieve regioselective modulation of the product molecules through the resonance between the solvent and allylpalladium. Additionally, the E‐form products were found to be thermodynamically stable.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"56 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-01-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142937432","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
The reaction of alkenyl boronates and bromodifluoroacetates in the presence of copper powder and TMEDA as the catalytic system was developed. The corresponding C–C coupling products were obtained in 35–93% yield. The method tolerated a variety of functional groups, namely, phenol, (thio)ether, protected amino-, hydroxy-, ketone, and carboxylic acid moieties, as well as various saturated carbo- and heterocycles, and was compatible with multigram scale-up (to 76 g). The diastereoselectivity of the process was typically low so that ca. 1:1 <i>E</i>/<i>Z</i> isomeric mixtures were formed from pure <i>E</i> or <i>Z</i> alkenyl boronates. Further functional group transformations demonstrated the utility of the prepared compounds as valuable building blocks for synthetic and medicinal chemistry. Based on the obtained results and the literature data, a plausible reaction mechanism was proposed involving the formation of radical and organocopper intermediates.
{"title":"Copper-mediated C–C Coupling of Alkenyl Boronates and Bromodifluoroacetates","authors":"Yevhen Yurov, Kamila Laniush, Oleksandr Hryshchuk, Oleksandr Liashuk, Oleksandr Grygorenko","doi":"10.1002/adsc.202401489","DOIUrl":"https://doi.org/10.1002/adsc.202401489","url":null,"abstract":"The reaction of alkenyl boronates and bromodifluoroacetates in the presence of copper powder and TMEDA as the catalytic system was developed. The corresponding C–C coupling products were obtained in 35–93% yield. The method tolerated a variety of functional groups, namely, phenol, (thio)ether, protected amino-, hydroxy-, ketone, and carboxylic acid moieties, as well as various saturated carbo- and heterocycles, and was compatible with multigram scale-up (to 76 g). The diastereoselectivity of the process was typically low so that ca. 1:1 <i>E</i>/<i>Z</i> isomeric mixtures were formed from pure <i>E</i> or <i>Z</i> alkenyl boronates. Further functional group transformations demonstrated the utility of the prepared compounds as valuable building blocks for synthetic and medicinal chemistry. Based on the obtained results and the literature data, a plausible reaction mechanism was proposed involving the formation of radical and organocopper intermediates.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"28 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-01-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142939640","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Guilherme Lutz, Fabiola Caldeira, Marcela Felix, Davi Back, Victor Deflon, Cristina Wayne Nogueira, Gilson Zeni
A methodology for the synthesis and functionalization of quinolines was developed. This approach involves the cyclization of 2-amino arylalkynyl ketones to 3-(organoselanyl)-4-iodoquinolines through a sequential reaction pathway. The process includes: (i) in situ formation of an electrophilic organoselenyl species, (ii) activation of the alkyne's carbon-carbon bond via a seleniranium ion intermediate, (iii) anti-nucleophilic attack of iodide on the activated triple bond, and (iv) subsequent condensation. The resulting 3-(organoselanyl)-4-iodoquinolines were demonstrated to be versatile substrates, efficiently undergoing Sonogashira cross-coupling to produce 4-alkynyl-quinolines and Ullmann-type reactions to yield the corresponding sulfides. Furthermore, the 4-alkynyl-quinolines were readily converted into selenophene derivatives via halogen-promoted electrophilic cyclization, highlighting the broad applicability of the developed method.
{"title":"Synthesis of 3-Organoselenyl Quinolines through the Reduction of Alkynes Mediated by Electrophilic Organoselenium Compounds","authors":"Guilherme Lutz, Fabiola Caldeira, Marcela Felix, Davi Back, Victor Deflon, Cristina Wayne Nogueira, Gilson Zeni","doi":"10.1002/adsc.202401514","DOIUrl":"https://doi.org/10.1002/adsc.202401514","url":null,"abstract":"A methodology for the synthesis and functionalization of quinolines was developed. This approach involves the cyclization of 2-amino arylalkynyl ketones to 3-(organoselanyl)-4-iodoquinolines through a sequential reaction pathway. The process includes: (i) in situ formation of an electrophilic organoselenyl species, (ii) activation of the alkyne's carbon-carbon bond via a seleniranium ion intermediate, (iii) anti-nucleophilic attack of iodide on the activated triple bond, and (iv) subsequent condensation. The resulting 3-(organoselanyl)-4-iodoquinolines were demonstrated to be versatile substrates, efficiently undergoing Sonogashira cross-coupling to produce 4-alkynyl-quinolines and Ullmann-type reactions to yield the corresponding sulfides. Furthermore, the 4-alkynyl-quinolines were readily converted into selenophene derivatives via halogen-promoted electrophilic cyclization, highlighting the broad applicability of the developed method.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"6 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-01-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142939638","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Maria Nicolas, Jan-Dirk Küsters-Spöring, Chiara Aufderheide, Helen Traving, Carina Kipp, Victoria Pfennig, Carsten Bolm, Petra Siegert, Dörte Rother
Chiral, vicinal diols are of high interest for academic research and industrial applications. For synthesizing chiral diols, enzymes are important catalysts due to their high selectivity and ability to work under tolerable temperature and no pressure. In this study, two consecutive enzyme-catalyzed steps were used for the asymmetric synthesis of aliphatic, vicinal diols with high product concentrations and chiral purity. The reaction comprised a ligation step employing lyases and a subsequent reduction step using oxidoreductases. Either in an aqueous buffer or an organic solvent, the potentially biobased aldehydes acetaldehyde, propanal, butanal, and pentanal were used as substrates. Here, all possible stereoisomers of 2,3-butanediol, 3,4-hexanediol, 4,5-octanediol, and 5,6-decanediol were produced with isomeric content values between 72% and > 99%, and concentrations and conversions between 4.1 and 60 mM. This work shows how four symmetric, chiral, vicinal diols can be synthesized by combining enzymes in a modular way, including exemplarily scaling.
{"title":"Enzymatic asymmetric synthesis of all stereoisomers of aliphatic, vicinal diols in conventional and non-conventional media","authors":"Maria Nicolas, Jan-Dirk Küsters-Spöring, Chiara Aufderheide, Helen Traving, Carina Kipp, Victoria Pfennig, Carsten Bolm, Petra Siegert, Dörte Rother","doi":"10.1002/adsc.202401143","DOIUrl":"https://doi.org/10.1002/adsc.202401143","url":null,"abstract":"Chiral, vicinal diols are of high interest for academic research and industrial applications. For synthesizing chiral diols, enzymes are important catalysts due to their high selectivity and ability to work under tolerable temperature and no pressure. In this study, two consecutive enzyme-catalyzed steps were used for the asymmetric synthesis of aliphatic, vicinal diols with high product concentrations and chiral purity. The reaction comprised a ligation step employing lyases and a subsequent reduction step using oxidoreductases. Either in an aqueous buffer or an organic solvent, the potentially biobased aldehydes acetaldehyde, propanal, butanal, and pentanal were used as substrates.\tHere, all possible stereoisomers of 2,3-butanediol,\u00003,4-hexanediol, 4,5-octanediol, and 5,6-decanediol were produced with isomeric content values between 72% and > 99%, and concentrations and conversions between 4.1 and 60 mM. This work shows how four symmetric, chiral, vicinal diols can be synthesized by combining enzymes in a modular way, including exemplarily scaling.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"28 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-01-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142939521","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Herein, we report a mild, operationally simple method for synthesis of α,α‐difluoroketones through selective single defluorination of trifluoroketones and subsequent difluoroalkylation of C(sp3)–H bonds at room temperature within a single step. By successfully difluoroalkylating unfunctionalized ethers and benzyl radical precursors, we demonstrated the broad applicability of this method. The mechanistic study supports that the success of the reaction is probably attributed to the dual roles of trimethylsilyl chloride under the photocatalyzed conditions: 1) fluoride anion scavenger; and 2) chlorine radical source which promote hydrogen atom transfer (HAT) reaction.
{"title":"Visible‐light‐induced Difluoroalkylation of C(sp3)–H Bonds with Trimethylsilyl Chloride as a Dual‐function Reagent","authors":"Xiaochen Wang, Senhui Wu, Pengxuan Ding, Yuxiu Liu, Hong-Jian Song, Qing-Min Wang","doi":"10.1002/adsc.202401497","DOIUrl":"https://doi.org/10.1002/adsc.202401497","url":null,"abstract":"Herein, we report a mild, operationally simple method for synthesis of α,α‐difluoroketones through selective single defluorination of trifluoroketones and subsequent difluoroalkylation of C(sp3)–H bonds at room temperature within a single step. By successfully difluoroalkylating unfunctionalized ethers and benzyl radical precursors, we demonstrated the broad applicability of this method. The mechanistic study supports that the success of the reaction is probably attributed to the dual roles of trimethylsilyl chloride under the photocatalyzed conditions: 1) fluoride anion scavenger; and 2) chlorine radical source which promote hydrogen atom transfer (HAT) reaction.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"14 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-01-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142937433","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Chuan-Hua Qu, Lin Zhu, Shan-Shan Chen, Hong-Bo Peng, Si-Si Zhang, Gui-Ting Song
Herein we reported for the first time a photocatalytic dearomative hydroacylation reaction of electron‐deficient indoles with readily available aromatic acids through a phosphoranyl radical‐assisted deoxygenative process. A range of racemic and optically active 2‐acylindoline derivatives were obtained in good yields (up to 94%) with good diastereoselectivity. The synthetic robustness is highlighted by the enantioselective dearomatization of indoles and the late‐stage modification of natural products and pharmaceutical molecules. This protocol features broad substrate scope and mild reaction conditions, providing a reliable entry to developing deoxygenative strategies in dearomatization reactions. Preliminary mechanistic studies and DFT calculations suggest that a Giese‐type radical addition pathway should be involved.
{"title":"Photoredox Hydroacylative Dearomatization of Indoles with Aromatic Carboxylic Acids","authors":"Chuan-Hua Qu, Lin Zhu, Shan-Shan Chen, Hong-Bo Peng, Si-Si Zhang, Gui-Ting Song","doi":"10.1002/adsc.202401401","DOIUrl":"https://doi.org/10.1002/adsc.202401401","url":null,"abstract":"Herein we reported for the first time a photocatalytic dearomative hydroacylation reaction of electron‐deficient indoles with readily available aromatic acids through a phosphoranyl radical‐assisted deoxygenative process. A range of racemic and optically active 2‐acylindoline derivatives were obtained in good yields (up to 94%) with good diastereoselectivity. The synthetic robustness is highlighted by the enantioselective dearomatization of indoles and the late‐stage modification of natural products and pharmaceutical molecules. This protocol features broad substrate scope and mild reaction conditions, providing a reliable entry to developing deoxygenative strategies in dearomatization reactions. Preliminary mechanistic studies and DFT calculations suggest that a Giese‐type radical addition pathway should be involved.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"4 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-01-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142935630","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Visible light, as an efficient and renewable resource, has gained significant attention in organic synthesis due to its mild, inexpensive, and environmentally friendly nature. Among the various photocatalytic processes, hydrogen atom transfer (HAT) has become a crucial mechanism for the activation of C−H bonds, with a particular focus on the functionalization of benzylic C(sp³)−H bonds. This review shows recent developments in the area of photoinduced HAT and its use in benzylic C−H bonds functionalization. We discuss halogen atom radicals, N‐centered radical, O‐centered radical, S‐centered radical and C‐centered radical in HAT processes, and influence on reaction selectivity and substrate versatility. The potential of photoinduced HAT to bypass the need for transition metal catalysts and directing groups positions it as a promising approach for constructing intricate organic molecules with high atom economy and sustainability. This review aims to offer a detailed summary of the current state of photoinduced HAT, providing insights into its potential uses in synthetic chemistry.
{"title":"Photoinduced Hydrogen Atom Transfer Activation of Benzylic C−H Bonds Functionalization","authors":"Guozhe Guo, Wen-Duo Li","doi":"10.1002/adsc.202401266","DOIUrl":"https://doi.org/10.1002/adsc.202401266","url":null,"abstract":"Visible light, as an efficient and renewable resource, has gained significant attention in organic synthesis due to its mild, inexpensive, and environmentally friendly nature. Among the various photocatalytic processes, hydrogen atom transfer (HAT) has become a crucial mechanism for the activation of C−H bonds, with a particular focus on the functionalization of benzylic C(sp³)−H bonds. This review shows recent developments in the area of photoinduced HAT and its use in benzylic C−H bonds functionalization. We discuss halogen atom radicals, N‐centered radical, O‐centered radical, S‐centered radical and C‐centered radical in HAT processes, and influence on reaction selectivity and substrate versatility. The potential of photoinduced HAT to bypass the need for transition metal catalysts and directing groups positions it as a promising approach for constructing intricate organic molecules with high atom economy and sustainability. This review aims to offer a detailed summary of the current state of photoinduced HAT, providing insights into its potential uses in synthetic chemistry.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"1 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-01-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142935625","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Hui-Shu Lin, Rongxiuyuan Huang, Xu Wang, Jin-Ping Fu, Yuyuan Liu, Yi Yi, Ying-ming Pan
An I2/cumene hydroperoxide (CHP)‐mediated tandem cyclization of 2‐aminoaryl ketone oximes with isocyanides has been developed. Various 2‐aminoquinazolines were obtained in 49‐96% yields under transition‐metal‐free conditions, and the resulting 4‐phenylquinazolin‐2‐amines show typical fluorescent emission properties. The key to the success of this strategy involves the formation of iminyl radical via the N‐O bond cleavage of hydroxy oxime.
{"title":"Synthesis of 2‐Aminoquinazolines through I2‐Catalyzed Cyclization of 2‐Aminoaryl Ketone Oximes and Isocyanides","authors":"Hui-Shu Lin, Rongxiuyuan Huang, Xu Wang, Jin-Ping Fu, Yuyuan Liu, Yi Yi, Ying-ming Pan","doi":"10.1002/adsc.202401463","DOIUrl":"https://doi.org/10.1002/adsc.202401463","url":null,"abstract":"An I2/cumene hydroperoxide (CHP)‐mediated tandem cyclization of 2‐aminoaryl ketone oximes with isocyanides has been developed. Various 2‐aminoquinazolines were obtained in 49‐96% yields under transition‐metal‐free conditions, and the resulting 4‐phenylquinazolin‐2‐amines show typical fluorescent emission properties. The key to the success of this strategy involves the formation of iminyl radical via the N‐O bond cleavage of hydroxy oxime.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"271 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-01-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142935626","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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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