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Photocatalyst for Visible-Light-Driven Sm(II)-Mediated Reductions
IF 4.9 1区 化学
Organic Letters Pub Date : 2024-12-11 DOI: 10.1021/acs.orglett.4c0372310.1021/acs.orglett.4c03723
Monika Tomar, Caroline Bosch, Jules Everaert, Rohan Bhimpuria, Anders Thapper, Andreas Orthaber and K. Eszter Borbas*, 
{"title":"Photocatalyst for Visible-Light-Driven Sm(II)-Mediated Reductions","authors":"Monika Tomar,&nbsp;Caroline Bosch,&nbsp;Jules Everaert,&nbsp;Rohan Bhimpuria,&nbsp;Anders Thapper,&nbsp;Andreas Orthaber and K. Eszter Borbas*,&nbsp;","doi":"10.1021/acs.orglett.4c0372310.1021/acs.orglett.4c03723","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c03723https://doi.org/10.1021/acs.orglett.4c03723","url":null,"abstract":"<p >Commercially available coumarin 343 in combination with reducible Sm(III) ions catalyzed divalent lanthanide-mediated C═O, C–halogen, P–Cl, and N═N reductions at ambient temperature in aqueous solvent mixtures. The catalyst absorbs visible light efficiently. The active divalent species is formed by photoinduced electron transfer from coumarin 343 to the stable trivalent precursor, and the coumarin could be regenerated by strictly 1 equiv of ascorbic acid.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"26 50","pages":"10752–10756 10752–10756"},"PeriodicalIF":4.9,"publicationDate":"2024-12-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.acs.org/doi/epdf/10.1021/acs.orglett.4c03723","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142858700","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
Quinazolinone-to-Isoquinoline Metamorphosis by Ruthenium-Catalyzed [4+2] Annulation with Sulfoxonium Ylides
IF 5.2 1区 化学
Organic Letters Pub Date : 2024-12-10 DOI: 10.1021/acs.orglett.4c04103
Xiaogang Wang, Fei Yuan, Michal Szostak
{"title":"Quinazolinone-to-Isoquinoline Metamorphosis by Ruthenium-Catalyzed [4+2] Annulation with Sulfoxonium Ylides","authors":"Xiaogang Wang, Fei Yuan, Michal Szostak","doi":"10.1021/acs.orglett.4c04103","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04103","url":null,"abstract":"Molecular editing of quinazolinones to isoquinolines by a novel ruthenium-catalyzed [4+2] annulation with sulfoxonium ylides has been developed. The method permits the precise and rapid assembly of multisubstituted aminoisoquinolines, a class of heterocycles that play a privileged role in organic synthesis and pharmaceutical development. This new catalytic process exhibits novel programmability, including directed C–H acetylation, nucleophilic cyclization, and alcoholysis. Remarkably, various 2-arylquinazolinones and sulfoxonium ylides could be employed in excellent yields with broad functional group tolerance. This heterocycle-to-heterocycle protocol is compatible with green chemistry using an EtOH solvent and releasing H<sub>2</sub>O and dimethyl sulfoxide as byproducts.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"77 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2024-12-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142797813","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-Catalyzed Asymmetric Tertiary Radical Cyanation for the Synthesis of Chiral Tetrasubstituted Monofluoroacyl Nitriles
IF 5.2 1区 化学
Organic Letters Pub Date : 2024-12-10 DOI: 10.1021/acs.orglett.4c03914
Li Liu, Qi Jiang, Long Tang, Chao Liu, Yanzhao Wang, Fanhong Wu, Jingjing Wu
{"title":"Copper-Catalyzed Asymmetric Tertiary Radical Cyanation for the Synthesis of Chiral Tetrasubstituted Monofluoroacyl Nitriles","authors":"Li Liu, Qi Jiang, Long Tang, Chao Liu, Yanzhao Wang, Fanhong Wu, Jingjing Wu","doi":"10.1021/acs.orglett.4c03914","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c03914","url":null,"abstract":"The construction of chiral tetrasubstituted α-fluoro-α-cyano carbonyl compounds remains a key challenge in synthetic organic chemistry because of their popularity in multiple disciplines. In this paper, we report the copper-catalyzed asymmetric fluorinated tertiary radical cyanation reaction of cyclic α-iodo-α-fluoroindanones with TMSCN to achieve chiral nitriles with carbon–fluorine quaternary stereogenic centers. Thus, an array of optically active tetrasubstituted monofluoroacyl nitriles were synthesized with high reaction efficiency and excellent enantioselectivities (up to 91% yield, 99% ee). Moreover, mechanistic investigations, including experiments, were conducted to clarify the reaction pathway and stereochemical outcomes.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"78 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2024-12-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142797811","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 Cascade Cyclization of 1-(2-(Arylethynyl)benzoyl)indoles into Sulfonated Benazepino[1,2-a]indolones
IF 5.2 1区 化学
Organic Letters Pub Date : 2024-12-10 DOI: 10.1021/acs.orglett.4c04145
Liangke Guo, Zhiyang Zhang, Fuyi Zhang, Kai Sun, Bing Yu
{"title":"Visible-Light-Induced Cascade Cyclization of 1-(2-(Arylethynyl)benzoyl)indoles into Sulfonated Benazepino[1,2-a]indolones","authors":"Liangke Guo, Zhiyang Zhang, Fuyi Zhang, Kai Sun, Bing Yu","doi":"10.1021/acs.orglett.4c04145","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04145","url":null,"abstract":"1-(2-(Arylethynyl)benzoyl)indoles were developed as an innovative scaffold for radical cascade cyclization under visible-light and mild conditions, enabling efficient synthesis of sulfonated benazepino[1,2-<i>a</i>]indolones. This method operates at room temperature and demonstrates broad substrate compatibility and scalability, with promising potential for sunlight-driven reactions.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"47 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2024-12-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142805051","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
Cu-Catalyzed Electrochemical Activation of Nitromethane to Access Aldoxime-Substituted Nitrile Oxide for Huisgen Reaction 铜催化电化学活化硝基甲烷以获得用于惠斯根反应的醛肟取代腈氧化物
IF 5.2 1区 化学
Organic Letters Pub Date : 2024-12-10 DOI: 10.1021/acs.orglett.4c04146
Zhichao Shao, Yulin Li, Liumin Wang, Tao Pan, Shuying Liu, Meng Xue, Lixing Zhao, Yuexia Zhang
{"title":"Cu-Catalyzed Electrochemical Activation of Nitromethane to Access Aldoxime-Substituted Nitrile Oxide for Huisgen Reaction","authors":"Zhichao Shao, Yulin Li, Liumin Wang, Tao Pan, Shuying Liu, Meng Xue, Lixing Zhao, Yuexia Zhang","doi":"10.1021/acs.orglett.4c04146","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04146","url":null,"abstract":"Here, we report an electrochemical approach to generate an aldoxime-substituted nitrile oxide via the activation of nitromethane. The Cu-catalyzed Huisgen reaction of this 1,3-dipole with alkynes enables successful preparation of 48 new isoxazole aldoximes, which are typically challenging to synthesize by other methods, in 52 to 97% yields with excellent regioselectivity and chemoselectivity in a single step. Moreover, 20 3,3′-bisisoxazoles are prepared from the isoxazole aldoxime products in good yields via a two-step sequence.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"20 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2024-12-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142797814","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
Rh(II)-Catalyzed Selective C(sp3)–H/C(sp2)–H Bonds Cascade Insertion to Construct [6–8–6] Benzo-Fused Scaffold
IF 5.2 1区 化学
Organic Letters Pub Date : 2024-12-10 DOI: 10.1021/acs.orglett.4c03619
Tao Yu, Feifei Fang, Haowen Shou, Yazhou Li, Zhiyan Qu, Feiyang Chen, Yu Zhang, Jiang Wang, Hong Liu
{"title":"Rh(II)-Catalyzed Selective C(sp3)–H/C(sp2)–H Bonds Cascade Insertion to Construct [6–8–6] Benzo-Fused Scaffold","authors":"Tao Yu, Feifei Fang, Haowen Shou, Yazhou Li, Zhiyan Qu, Feiyang Chen, Yu Zhang, Jiang Wang, Hong Liu","doi":"10.1021/acs.orglett.4c03619","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c03619","url":null,"abstract":"The fused eight-membered carbocycles (EMCs) play vital roles in the medicinal and biological investigations of many natural products and marketed drugs. The traditional synthesis of [6–8–6] benzo-fused derivatives involves multistep reactions and low yields, making the development of a one-step synthesis method a more challenging work. Here, we present a novel strategy for one-step construction of [6–8–6] benzo-fused scaffold from propargyl diazoacetates substituted with benzyl-nitrogen heterocyclic ring via Rh(ll)-catalyzed carbene/alkyne metathesis (CAM) and selective C–H bond insertion. This method exhibits a specific substrate scope, simple operation, mild reaction conditions, and high atom efficiency. Mechanistically, the process involves sequential CAM, 1,3-H-shift, intramolecular nucleophilic attack, and selective C(sp<sup>3</sup>)–H/C(sp<sup>2</sup>)–H bonds cascade insertion. Notably, the unique spirocyclic zwitterionic intermediate generated in this sequence contributes to <i>N</i>-heterocycle migration and fused eight-membered carbocycle formation. Additionally, the C(sp<sup>3</sup>)–H bond insertion connected to the oxygen atom rather than the nitrogen atom has been unexpectedly confirmed with the assistance of the spirocyclic zwitterionic intermediate. Overall, our findings open up a new avenue for the construction of [6–8–6] benzo-fused scaffold.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"71 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2024-12-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142805047","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-Catalyzed Asymmetric Tertiary Radical Cyanation for the Synthesis of Chiral Tetrasubstituted Monofluoroacyl Nitriles
IF 4.9 1区 化学
Organic Letters Pub Date : 2024-12-10 DOI: 10.1021/acs.orglett.4c0391410.1021/acs.orglett.4c03914
Li Liu, Qi Jiang, Long Tang, Chao Liu, Yanzhao Wang*, Fanhong Wu* and Jingjing Wu*, 
{"title":"Copper-Catalyzed Asymmetric Tertiary Radical Cyanation for the Synthesis of Chiral Tetrasubstituted Monofluoroacyl Nitriles","authors":"Li Liu,&nbsp;Qi Jiang,&nbsp;Long Tang,&nbsp;Chao Liu,&nbsp;Yanzhao Wang*,&nbsp;Fanhong Wu* and Jingjing Wu*,&nbsp;","doi":"10.1021/acs.orglett.4c0391410.1021/acs.orglett.4c03914","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c03914https://doi.org/10.1021/acs.orglett.4c03914","url":null,"abstract":"<p >The construction of chiral tetrasubstituted α-fluoro-α-cyano carbonyl compounds remains a key challenge in synthetic organic chemistry because of their popularity in multiple disciplines. In this paper, we report the copper-catalyzed asymmetric fluorinated tertiary radical cyanation reaction of cyclic α-iodo-α-fluoroindanones with TMSCN to achieve chiral nitriles with carbon–fluorine quaternary stereogenic centers. Thus, an array of optically active tetrasubstituted monofluoroacyl nitriles were synthesized with high reaction efficiency and excellent enantioselectivities (up to 91% yield, 99% ee). Moreover, mechanistic investigations, including experiments, were conducted to clarify the reaction pathway and stereochemical outcomes.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"26 50","pages":"10833–10839 10833–10839"},"PeriodicalIF":4.9,"publicationDate":"2024-12-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142858624","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-Mediated Nucleophilic Addition of Alkene with Aldehyde: Synthesis of Secondary Alcohols
IF 4.9 1区 化学
Organic Letters Pub Date : 2024-12-10 DOI: 10.1021/acs.orglett.4c0381910.1021/acs.orglett.4c03819
Du Hu, Haowen Dang, Zhen Liang, Donghao Wang, Yunyun Du, Chao Shen, Jiabin Shen* and Min Wang*, 
{"title":"Visible-Light-Mediated Nucleophilic Addition of Alkene with Aldehyde: Synthesis of Secondary Alcohols","authors":"Du Hu,&nbsp;Haowen Dang,&nbsp;Zhen Liang,&nbsp;Donghao Wang,&nbsp;Yunyun Du,&nbsp;Chao Shen,&nbsp;Jiabin Shen* and Min Wang*,&nbsp;","doi":"10.1021/acs.orglett.4c0381910.1021/acs.orglett.4c03819","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c03819https://doi.org/10.1021/acs.orglett.4c03819","url":null,"abstract":"<p >Herein, a photocatalytic strategy for the synthesis of secondary alcohols by nucleophilic addition of an alkene with an aldehyde is described. This operationally simple methodology opens an approach for the synthesis of alcohols using commercially available reagents in moderate to excellent yields. Mechanistic studies indicate that the formation of the radical anion from alkene via single-electron transfer is the key step in this reaction.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"26 50","pages":"10797–10802 10797–10802"},"PeriodicalIF":4.9,"publicationDate":"2024-12-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142858663","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-Mediated Nucleophilic Addition of Alkene with Aldehyde: Synthesis of Secondary Alcohols
IF 5.2 1区 化学
Organic Letters Pub Date : 2024-12-10 DOI: 10.1021/acs.orglett.4c03819
Du Hu, Haowen Dang, Zhen Liang, Donghao Wang, Yunyun Du, Chao Shen, Jiabin Shen, Min Wang
{"title":"Visible-Light-Mediated Nucleophilic Addition of Alkene with Aldehyde: Synthesis of Secondary Alcohols","authors":"Du Hu, Haowen Dang, Zhen Liang, Donghao Wang, Yunyun Du, Chao Shen, Jiabin Shen, Min Wang","doi":"10.1021/acs.orglett.4c03819","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c03819","url":null,"abstract":"Herein, a photocatalytic strategy for the synthesis of secondary alcohols by nucleophilic addition of an alkene with an aldehyde is described. This operationally simple methodology opens an approach for the synthesis of alcohols using commercially available reagents in moderate to excellent yields. Mechanistic studies indicate that the formation of the radical anion from alkene via single-electron transfer is the key step in this reaction.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"38 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2024-12-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142805048","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
Late-Stage Functionalization of Guanine-Based Nucleosides, Nucleotides, and Oligonucleotide: Synthesis and Derivatization of Tricyclic Nucleoside Analogues 鸟嘌呤核苷、核苷酸和寡核苷酸的后期功能化：三环核苷类似物的合成和衍生化
IF 5.2 1区 化学
Organic Letters Pub Date : 2024-12-10 DOI: 10.1021/acs.orglett.4c04024
Ao-Di Ma, Wei-Jia Chen, Wen-Wu Sun, Bin Wu
{"title":"Late-Stage Functionalization of Guanine-Based Nucleosides, Nucleotides, and Oligonucleotide: Synthesis and Derivatization of Tricyclic Nucleoside Analogues","authors":"Ao-Di Ma, Wei-Jia Chen, Wen-Wu Sun, Bin Wu","doi":"10.1021/acs.orglett.4c04024","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04024","url":null,"abstract":"We report here the synthesis of tricyclic nucleoside analogues via acid-catalyzed cyclization of guanine with 1,1,3,3-tetramethoxypropane. The method enables the use of hydroxyl-unprotected antiviral drugs (acyclovir, ganciclovir, and penciclovir), guanosines, oligonucleotide, and triazole-linked nucleoside dimers as substrates. Nucleoside trimer and tetramer were synthesized by derivatization reactions.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"23 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2024-12-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142797812","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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