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Pyridyloxy-Directed, Pd(II)-Catalyzed Late-Stage C(sp2)-H Alkynylation and Olefination of Tyrosine Oligopeptides. 吡啶氧导向，Pd（II）催化酪氨酸寡肽后期C(sp2)-H炔化和烯烃化。
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-05-19 DOI: 10.1021/acs.joc.5c00118
Qing-Sheng Zhao,Shu Yang,Ting-Ting Guo,Jian-Bo Ma,Xiao-Hong Cheng,Sheng-Jiao Yan
{"title":"Pyridyloxy-Directed, Pd(II)-Catalyzed Late-Stage C(sp2)-H Alkynylation and Olefination of Tyrosine Oligopeptides.","authors":"Qing-Sheng Zhao,Shu Yang,Ting-Ting Guo,Jian-Bo Ma,Xiao-Hong Cheng,Sheng-Jiao Yan","doi":"10.1021/acs.joc.5c00118","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00118","url":null,"abstract":"Peptides and peptidomimetics have gained increasing interest as therapeutics due to their unique properties as small molecules and proteins. Herein, we report the pyridyloxy-directed Pd (II)-catalyzed C(sp2)-H alkynylation and olefination of tyrosine residues in peptides with high chemo- and site-selectivity. This method achieved the functionalization of tyrosine at any position of the amino acid for alkynylation and olefination. Furthermore, this approach can be used to synthesize peptide-biomolecule conjugates.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"17 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-05-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144087796","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}
引用次数: 0
Fe-Catalyzed Radical Trifluoromethylation and Cyclization of Ortho-Vinyl Enaminones with 1-(Trifluoromethyl)-1,3-benzo-[d][1,2]iodaoxol-3(1H)-one to Construct Functionalized Quinolines. 铁催化邻乙烯基胺酮与1-（三氟甲基）-1,3-苯并-[d][1,2]碘-3(1H)- 1自由基三氟甲基化和环化构建功能化喹啉。
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-05-19 DOI: 10.1021/acs.joc.5c00811
Qin Luo,Zhi-Bo Xie,Cen Jian,Kun-Rong Yang,Kun Huang,Sheng-Jiao Yan
{"title":"Fe-Catalyzed Radical Trifluoromethylation and Cyclization of Ortho-Vinyl Enaminones with 1-(Trifluoromethyl)-1,3-benzo-[d][1,2]iodaoxol-3(1H)-one to Construct Functionalized Quinolines.","authors":"Qin Luo,Zhi-Bo Xie,Cen Jian,Kun-Rong Yang,Kun Huang,Sheng-Jiao Yan","doi":"10.1021/acs.joc.5c00811","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00811","url":null,"abstract":"Herein, we present a protocol for the construction of functionalized quinolines, i.e., 3-acyl-4-(2,2,2-trifluoro-ethyl)quinolines (ATFQLs) 4, from ortho-vinyl enaminones and 1-(trifluoromethyl)-1,3-benzo-[d][1,2]-iodaoxol-3(1H)-one, which was catalyzed by FeCp2 and promoted by FeCl3 (Lewis acid) additives in solvents (i.e., acetonitrile and toluene). This strategy first utilized the FeCp2-catalyzed functionalization of alkenes with trifluoromethyl radicals. The intermediate formed was captured by the ortho-iodobenzoate substrate, yielding intermediate 3, which then underwent the FeCl3-catalyzed elimination of ortho-iodobenzoate at a higher temperature to form an α,β-unsaturated intermediate. The subsequent intramolecular Michael reaction of the intermediate yielded the final target compound 4. In summary, a series of ATFQLs 4 were synthesized through the formation of two bonds (C═C and C-C).","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"9 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-05-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144087795","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}
引用次数: 0
Ruthenium-Catalyzed Decarboxylative Direct 2-Pyridination of α,β-Unsaturated Carboxylic Acids. 钌催化α，β-不饱和羧酸的脱羧直接2-吡啶化。
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-05-19 DOI: 10.1021/acs.joc.5c00375
Jiaojiao Guo,Ying Zhu,Jing Zhang
{"title":"Ruthenium-Catalyzed Decarboxylative Direct 2-Pyridination of α,β-Unsaturated Carboxylic Acids.","authors":"Jiaojiao Guo,Ying Zhu,Jing Zhang","doi":"10.1021/acs.joc.5c00375","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00375","url":null,"abstract":"We report a ruthenium-catalyzed decarboxylative direct mono-2-pyridination of α,β-unsaturated carboxylic acids, offering a selective method for synthesizing 2-(1-arylalkenyl)pyridines. Under redox-neutral conditions, the reaction demonstrates broad substrate scope, high functional group tolerance, and significant potential for further derivatization. Mechanistic studies reveal that selective activation of the allylic C(sp3)-H bond, directed by the pyridine group, underpins the observed mono-2-pyridination. This work provides an efficient and selective strategy for the catalytic decarboxylative transformation of α,β-unsaturated carboxylic acids, expanding the toolbox for functionalizing pyridine derivatives.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"2 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-05-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144087793","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}
引用次数: 0
Conjugated Donor-Acceptor Macrocycles: Synthesis and Oxidation of ortho-Phenylene Bridged Cyclic Tetra(benzo[c][1,2,5]thiadiazole). 共轭给受体大环：邻苯二烯桥接环四元（苯并[c][1,2,5]噻二唑）的合成与氧化。
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-05-18 DOI: 10.1021/acs.joc.5c00373
Zhihao Ma,Shijun Gu,Xiuqin Lu,Keisuke Tajima,Fengkun Chen
{"title":"Conjugated Donor-Acceptor Macrocycles: Synthesis and Oxidation of ortho-Phenylene Bridged Cyclic Tetra(benzo[c][1,2,5]thiadiazole).","authors":"Zhihao Ma,Shijun Gu,Xiuqin Lu,Keisuke Tajima,Fengkun Chen","doi":"10.1021/acs.joc.5c00373","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00373","url":null,"abstract":"Here, we reported the synthesis of an ortho-phenylene bridged cyclic tetra(benzo[c][1,2,5]thiadiazole) (3) by stepwise Suzuki-Miyaura couplings. Subsequent oxidation of 3 yielded a two-sided fused product 4, identified as an ortho-phenylene bridged cyclic triphenyleno[1,2-c:7,8-c']bis([1,2,5]thiadiazole) dimer. The structures of 3 and 4 were confirmed by high-resolution mass spectroscopies (HRMS) and NMR techniques. Their photophysical and electrochemical properties were fully characterized by ultraviolet-visible (UV-vis), fluorescence spectroscopy, cyclic voltammetry, and density functional theory (DFT) calculations.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"56 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-05-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144087797","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}
引用次数: 0
Strain-Release-Driven Alder-Ene Reaction of Bicyclo[1.1.0]butanes with β-Fluoroalkyl-α,β-Unsaturated Ketones. 菌株释放驱动的双环[1.1.0]丁烷与β-氟烷基-α、β-不饱和酮的醛烯反应
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-05-18 DOI: 10.1021/acs.joc.5c00455
Wenjie Xu,Zhiyi Zhang,Hao Wu,Dachang Bai
{"title":"Strain-Release-Driven Alder-Ene Reaction of Bicyclo[1.1.0]butanes with β-Fluoroalkyl-α,β-Unsaturated Ketones.","authors":"Wenjie Xu,Zhiyi Zhang,Hao Wu,Dachang Bai","doi":"10.1021/acs.joc.5c00455","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00455","url":null,"abstract":"The Alder-ene reaction of the C-C bond in bicyclo[1.1.0]butanes would provide a unique and efficient synthesis route for cyclobutene frameworks. Herein, we report a regio- and diastereoselective Alder-ene reaction of bicyclo[1.1.0]butanes with β-fluoroalkyl-α,β-unsaturated ketones, giving a wide variety of cyclobutenes with two contiguous centers and diene products. The reaction features atoms and step economies and exhibits broad substrate scope. Several downstream transformations of these cyclobutenes were performed.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"24 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-05-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144087725","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}
引用次数: 0
Synthesis of 3,6-Dihydro-2H-thiopyrans from α-Diazo-β-diketones and Vinylthiiranes via [5 + 1] Annulation [5 + 1]环法制备α-重氮-β-二酮与乙烯基硫烷合成3,6-二氢- 2h -硫吡喃
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-05-17 DOI: 10.1021/acs.joc.5c00330
Yinqiao Wang, Jiaxi Xu
{"title":"Synthesis of 3,6-Dihydro-2H-thiopyrans from α-Diazo-β-diketones and Vinylthiiranes via [5 + 1] Annulation","authors":"Yinqiao Wang, Jiaxi Xu","doi":"10.1021/acs.joc.5c00330","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00330","url":null,"abstract":"Functionalized 3,6-dihydro-2<i>H</i>-thiopyrans are synthesized in moderate to good yields from α-diazo-β-diketones and vinylthiiranes under Cu(hfacac)<sub>2</sub> catalysis and microwave irradiation via [5 + 1] annulation. The reaction mechanism includes a tandem sequence of the Cu-carbenoid generation from α-diazo-β-diketones, nucleophilic attack of vinylthiiranes to the carbenoids, and subsequent [2,3]-sigmatropic rearrangement. The process is a carbene-induced ring expansion of vinylthiiranes.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"77 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-05-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144067334","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}
引用次数: 0
Ru-Catalyzed Asymmetric Hydrogenation of Chiral δ-Hydroxy-β-Keto Acid Derivatives 钌催化手性δ-羟基-β-酮酸衍生物的不对称加氢反应
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-05-17 DOI: 10.1021/acs.joc.4c02766
Limin Xu, Yuxuan Zhang, Yan Lu, Zhaoguo Zhang
{"title":"Ru-Catalyzed Asymmetric Hydrogenation of Chiral δ-Hydroxy-β-Keto Acid Derivatives","authors":"Limin Xu, Yuxuan Zhang, Yan Lu, Zhaoguo Zhang","doi":"10.1021/acs.joc.4c02766","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02766","url":null,"abstract":"Ru-catalyzed stereoselective asymmetric hydrogenation of multifunctionalized ketones has been a formidable challenge, and few related successful works have been reported. Herein, we report our research on Ru-catalyzed asymmetric hydrogenation of chiral δ-hydroxy-β-keto acid derivatives, which achieves excellent diastereoselectivity (up to &gt;99% <i>de</i>). This procedure provides a new route for the synthesis of pure <i>syn</i>- and <i>anti</i>-3,5-dihydroxy acid derivatives, which serve as key intermediates in natural products and drug molecules, such as statins.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"127 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-05-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144067333","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}
引用次数: 0
[3 + 2] Cycloaddition of N-Amino(iso)quinolinium Salts with Vinylsulfonium Salt: Synthesis of Pyrazolo[1,5-a]quinoline and Pyrazolo[5,1-a]isoquinoline Derivatives [3 + 2] n -氨基（异）喹啉盐与乙烯基磺酸盐的环加成：吡唑啉[1,5-a]喹啉和吡唑啉[5,1-a]异喹啉衍生物的合成
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-05-16 DOI: 10.1021/acs.joc.5c00377
Hui Wu, Wenfeng Zhao, Nan Jiang, Mao Liu, Qingmei Ge, Hang Cong
{"title":"[3 + 2] Cycloaddition of N-Amino(iso)quinolinium Salts with Vinylsulfonium Salt: Synthesis of Pyrazolo[1,5-a]quinoline and Pyrazolo[5,1-a]isoquinoline Derivatives","authors":"Hui Wu, Wenfeng Zhao, Nan Jiang, Mao Liu, Qingmei Ge, Hang Cong","doi":"10.1021/acs.joc.5c00377","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00377","url":null,"abstract":"In this study, we reported the utilization of vinylsulfonium salt as a highly efficient dipolarophile, leveraging the facile leaving ability of its sulfide moiety, to engage in a [3 + 2] cycloaddition with <i>N</i>-amino(iso)quinolinium salts. This approach facilitates the construction of various C<sub>1</sub>/C<sub>2</sub>-unsubstituted pyrazolo(iso)quinoline skeletons. The transformation is conducted under catalyst- and external oxidant-free conditions. Furthermore, the extended gram-scale reaction demonstrates the practical applicability of the developed protocol.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"8 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-05-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144066178","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}
引用次数: 0
Visible Light-Induced Cascade Phosphorylation/Cyclization to Access Phosphorus-Containing Diazocinocarbazoles. 可见光诱导级联磷酸化/环化以获得含磷重氮氨基咔唑。
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-05-16 DOI: 10.1021/acs.joc.5c00713
Yifan Yin,Fei Liu,Miao Tian,Liangliang Han,Minghan Li,Jianfeng Tao,Qian Liu,Lianglong Sun,Xinming Xu,Kai Sun
{"title":"Visible Light-Induced Cascade Phosphorylation/Cyclization to Access Phosphorus-Containing Diazocinocarbazoles.","authors":"Yifan Yin,Fei Liu,Miao Tian,Liangliang Han,Minghan Li,Jianfeng Tao,Qian Liu,Lianglong Sun,Xinming Xu,Kai Sun","doi":"10.1021/acs.joc.5c00713","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00713","url":null,"abstract":"Herein, we developed a novel radical cascade phosphorylation/cyclization strategy to access phosphorus-containing diazocine-fused carbazoles in moderate to good yields, offering expanded opportunities for the exploration of biologically active molecules. This method features metal-free photochemical tandem, mild conditions, broad substrate scopes, and scale-up ability. Mechanistic experiments implied that this photocatalyzed phosphorylation/cyclization reaction was realized by a sequence of EnT/SET/SET/radical addition/cyclization/SET/deprotonation processes.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"29 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-05-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144065685","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}
引用次数: 0
A One-Pot Synthesis of Substituted Pyrrolo[2,1-a]isoquinolines via an Oxidation/Annulation Sequence of 2-(3,4-Dihydroisoquinolin-2(1H)-yl)malononitriles. 2-（3,4-二氢异喹啉-2(1H)-基）丙二腈的氧化/环化序列一锅法合成取代吡咯[2,1- A]异喹啉
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-05-15 DOI: 10.1021/acs.joc.5c00639
Bang-Hong Zhang,Kai-Long Hou,Run-Ze Li,Fang-Fang Qiu,Ge-Ge Liu,Zi-Qin Wei,Wen Bao,Ye Zhang,Dao-Yong Zhu,Shao-Hua Wang
{"title":"A One-Pot Synthesis of Substituted Pyrrolo[2,1-a]isoquinolines via an Oxidation/Annulation Sequence of 2-(3,4-Dihydroisoquinolin-2(1H)-yl)malononitriles.","authors":"Bang-Hong Zhang,Kai-Long Hou,Run-Ze Li,Fang-Fang Qiu,Ge-Ge Liu,Zi-Qin Wei,Wen Bao,Ye Zhang,Dao-Yong Zhu,Shao-Hua Wang","doi":"10.1021/acs.joc.5c00639","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00639","url":null,"abstract":"A highly effective oxidation/annulation reaction between 2-isocyanoacetates and 2-(3,4-dihydroisoquinolin-2(1H)-yl)malononitriles has been successfully developed to give substituted pyrrolo[2,1-a]isoquinoline derivatives with moderate to good yields in a one-pot manner.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"28 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-05-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143991994","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}
引用次数: 0
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