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Visible-Light-Driven Benzylic C-H Oxidation Catalyzed by Bisphosphonium Salt. 双膦盐催化可见光驱动苯基C-H氧化。
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-05-14 DOI: 10.1021/acs.joc.5c00495
Anfen Zhang,Wenfeng Zhao,Nan Jiang,Mao Liu,Qingmei Ge,Hang Cong
{"title":"Visible-Light-Driven Benzylic C-H Oxidation Catalyzed by Bisphosphonium Salt.","authors":"Anfen Zhang,Wenfeng Zhao,Nan Jiang,Mao Liu,Qingmei Ge,Hang Cong","doi":"10.1021/acs.joc.5c00495","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00495","url":null,"abstract":"An efficient photocatalytic method for the synthesis of carbonyl compounds through the oxidation of benzyl C-H bonds was developed. A series of acetophenone derivatives were successfully synthesized by utilizing a bisphosphonium salt catalyst and molecular oxygen as the oxidant. Preliminary mechanistic studies indicated that the reaction mechanism involved a free-radical pathway.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"74 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-05-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143945236","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
Gold-Catalyzed Intramolecular Coupling Reduction for Direct Synthesis of Indole-Fused Iminosugars. 金催化的分子内偶联还原直接合成吲哚-融合亚糖。
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-05-14 DOI: 10.1021/acs.joc.5c00593
Lijing Feng,Likai Zhou,Weilin Yang,Xiaoyan Huang,Yuhui Liu,Jilai Wu,Chao Wei,Hua Chen
{"title":"Gold-Catalyzed Intramolecular Coupling Reduction for Direct Synthesis of Indole-Fused Iminosugars.","authors":"Lijing Feng,Likai Zhou,Weilin Yang,Xiaoyan Huang,Yuhui Liu,Jilai Wu,Chao Wei,Hua Chen","doi":"10.1021/acs.joc.5c00593","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00593","url":null,"abstract":"In the presence of Hantzsch ester and with JohnPhosAuCl/AgOMs as catalysts, a series of indole-fused iminosugars were obtained in good yields by the intramolecular reductive coupling reaction of iminosugar C-glycoside, in which the terminal alkyne could be coupled with indole and further reduced to methyl. The substrates of iminosugar C-glycosides were conveniently prepared by a three-component reaction of tosylated/mesylated sugar, propargylamine, and indole derivatives. The advantages of this protocol are its simplicity and efficiency in constructing the complex indole-fused iminosugars.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"1 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-05-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143945237","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
Photoinduced PhI(OAc)2-Mediated Cross-Dehydrogenative Heteroarylation of Aldehydes 光诱导PhI(OAc)2介导的醛的交叉脱氢异芳基化
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-05-14 DOI: 10.1021/acs.joc.5c00655
Lusina Mantry, Parthasarathy Gandeepan
{"title":"Photoinduced PhI(OAc)2-Mediated Cross-Dehydrogenative Heteroarylation of Aldehydes","authors":"Lusina Mantry, Parthasarathy Gandeepan","doi":"10.1021/acs.joc.5c00655","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00655","url":null,"abstract":"Direct acylation of heteroarenes with aldehydes has been established through a photoinduced hypervalent iodine-mediated cross-dehydrogenative coupling reaction. The reaction proceeds through the in situ generation of nucleophilic acyl radicals from aldehydes via acyl C–H hydrogen atom transfer (HAT), followed by a Minisci-type reaction with heteroarenes. The developed reaction system proved to be suitable for cross-coupling a diverse range of heterocycles and aldehydes.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"6 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-05-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143945804","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
Total Synthesis of (-)-Herbindoles A, B, and C and (+)-trans-Herbindole A via a Convergent Benzannulation Strategy. （-）-苯并多酚A、B、C和(+)-反式苯并多酚A的聚合苯并合成
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-05-14 DOI: 10.1021/acs.joc.5c00653
Nathan H Faialaga,Rick L Danheiser
{"title":"Total Synthesis of (-)-Herbindoles A, B, and C and (+)-trans-Herbindole A via a Convergent Benzannulation Strategy.","authors":"Nathan H Faialaga,Rick L Danheiser","doi":"10.1021/acs.joc.5c00653","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00653","url":null,"abstract":"The herbindoles are cyclopent[g]indole alkaloids whose structures incorporate a fully substituted benzenoid ring and, as such, have served as useful platforms for the testing and refinement of methods for the construction of highly substituted indoles. Herein we report efficient and convergent total syntheses of four herbindole alkaloids, including the first enantioselective total synthesis of trans-(+)-herbindole A. The pivotal step in the synthetic strategy is the application of our vinylketene-based benzannulation in which a thermal Wolff rearrangement generates a vinylketene which combines with an ynamide derivative in the first step of a pericyclic cascade that produces a highly substituted aniline intermediate primed for cyclization to form the cyclopent[g]indole ring system. Subsequent cross-coupling reactions allow for the elaboration of a common precursor to herbindoles of the A, B, and C series.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"4 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-05-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143945347","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
Construction of C-S and C-Se Bonds via Photocatalytic Aromatization-Driven Deconstructive Diversification of Spiro-Dihydroquinazolinones Derived from Unstrained Ketones. 光催化芳构化驱动的非张力酮衍生螺-二氢喹唑啉酮的C-S和C-Se键构建
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-05-13 DOI: 10.1021/acs.joc.5c00499
Tao Wang,Jin-Long Dai,Yi-Feng Jiang,Shenghu Yan,Jia-Yin Wang
{"title":"Construction of C-S and C-Se Bonds via Photocatalytic Aromatization-Driven Deconstructive Diversification of Spiro-Dihydroquinazolinones Derived from Unstrained Ketones.","authors":"Tao Wang,Jin-Long Dai,Yi-Feng Jiang,Shenghu Yan,Jia-Yin Wang","doi":"10.1021/acs.joc.5c00499","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00499","url":null,"abstract":"A novel and robust deconstructive functionalization reaction of spiro-dihydroquinazolinones with sulfenylating reagents in the presence of base has been realized under visible light irradiation. This reaction enabled the direct ring-opening of unstrained cyclic ring systems, producing skeletally diverse functionalized quinazolinones with moderate to good yields. A range variety of sulfenylating reagents including diaryl disulfide, thiosulfonate, dithiosulfonate and 1-[(trifluoromethyl)thio]-2,5-pyrrolidinedione were compatible for this transformation. In addition, diaryl diselenide and selenosulfonate could also couple with spiro-dihydroquinazolinones to form C-Se Bonds. Mechanistic studies revealed that the reaction proceeds via a radical-radical coupling pathway.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"27 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-05-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143945292","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
Iron-Catalyzed Three-Component Reactions of Cyclopropanols with Alkenes and N-Heteroarenes via Ring-Opening and C-H Functionalization. 铁催化环丙醇与烯烃和n-杂芳烃的开环和碳氢官能化三组分反应。
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-05-13 DOI: 10.1021/acs.joc.5c00853
Jie Yang,Shuang Wu,Yan-Lin Chu,Ming Hu,Jin-Heng Li
{"title":"Iron-Catalyzed Three-Component Reactions of Cyclopropanols with Alkenes and N-Heteroarenes via Ring-Opening and C-H Functionalization.","authors":"Jie Yang,Shuang Wu,Yan-Lin Chu,Ming Hu,Jin-Heng Li","doi":"10.1021/acs.joc.5c00853","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00853","url":null,"abstract":"An iron-catalyzed ring-opening multicomponent reaction of cyclopropyl alcohols with alkenes and N-heteroarenes involving aryl C(sp2)-H functionalization was developed. This protocol facilitates the regioselective introduction of both the β-carbonyl moiety and an N-heteroarene group across the C═C bond of the alkene, thus allowing a straightforward, efficient, and facile access to 5-heteroarene ketones. In this process, this strategy relies on β-carbonyl alkyl radical formation from the ring-opening of cyclopropyl alcohols, addition across C═C bonds, and heteroaryl C(sp2)-H functionalization cascades. This general approach displays excellent selectivity control and broad functional-group tolerance.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"29 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-05-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143945345","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
Central-to-Axial-to-Central Chirality Transfer in the Au(I)-Catalyzed Cycloisomerization of Propargyl Vinyl Ethers to Cyclopentadienes. 金(I)催化丙炔乙烯基醚环异构化反应中中心-轴-中心手性转移。
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-05-13 DOI: 10.1021/acs.joc.5c00433
Dina Scarpi,Giovanni Turchi,Matteo Fazzini,Lucilla Favero,Ernesto G Occhiato
{"title":"Central-to-Axial-to-Central Chirality Transfer in the Au(I)-Catalyzed Cycloisomerization of Propargyl Vinyl Ethers to Cyclopentadienes.","authors":"Dina Scarpi,Giovanni Turchi,Matteo Fazzini,Lucilla Favero,Ernesto G Occhiato","doi":"10.1021/acs.joc.5c00433","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00433","url":null,"abstract":"An easy approach to the enantioselective synthesis of five-, six-, and seven-membered ring-fused cyclopentadienes (85-99% ee) is based on the Au(I)-catalyzed cycloisomerization of enantiomerically pure or enriched propargyl vinyl ethers, which occurs with complete central-to-axial-to-central chirality transfer. DFT calculations show that the formation of a nonplanar σ-Au(I)-pentadienyl cation intermediate having a helical configuration, which quickly cyclizes to form the target cyclopentadiene, accounts for the lack of erosion of the initial optical purity. From a synthetic point of view, when the cyclopentadienes are subjected to a quick 1,5-H shift and cannot be isolated as pure regioisomers, they can be trapped in situ by suitable dienophiles during or immediately after the gold(I)-catalyzed cycloisomerization to form more complex polycyclic compounds. The synthesis of an enantiomerically pure α-tertiary amine was realized to demonstrate the usefulness of this approach.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"42 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-05-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143945105","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
Rhodium-Catalyzed Aromatic C-H Allylation with α,β-Unsaturated Imines. 铑催化芳香C-H烯丙基化与α，β-不饱和亚胺。
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-05-13 DOI: 10.1021/acs.joc.5c00484
Wei-Tao Hu,Zhong-Xia Wang
{"title":"Rhodium-Catalyzed Aromatic C-H Allylation with α,β-Unsaturated Imines.","authors":"Wei-Tao Hu,Zhong-Xia Wang","doi":"10.1021/acs.joc.5c00484","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00484","url":null,"abstract":"Reaction of 2-arylpyridines with α,β-unsaturated imines in the presence of 2.5 mol % of [Cp*RhCl2]2 and 10 mol % of AgSbF6 in acetone affords allylated 2-arylpyridines with an enamine unit located in the allyl segment. This method features ortho-monoallylation selectivity and Z-selectivity of the C-C double bonds, is applicable to a wide range of substrates, and is compatible with air and functional groups such as halides, CF3, COOMe, OH, MeO, and ketal groups.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"113 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-05-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143945343","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
Fluorescence Emissive Fluorinated Pyrimido[5,4-h]quinazolines: Synthesis, Structure, and Photophysical and Halochromic Properties. 荧光发射氟化嘧啶[5,4-h]喹唑啉：合成、结构、光物理和变色性质。
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-05-13 DOI: 10.1021/acs.joc.5c00506
Kirti Yadav,Taro Udagawa,Yasuhiro Kubota,Toshiyasu Inuzuka,Govindarajan Krishnamoorthy,Kazumasa Funabiki
{"title":"Fluorescence Emissive Fluorinated Pyrimido[5,4-h]quinazolines: Synthesis, Structure, and Photophysical and Halochromic Properties.","authors":"Kirti Yadav,Taro Udagawa,Yasuhiro Kubota,Toshiyasu Inuzuka,Govindarajan Krishnamoorthy,Kazumasa Funabiki","doi":"10.1021/acs.joc.5c00506","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00506","url":null,"abstract":"Planar tricyclic aromatics and azaheteroaromatics are of significant interest to organic chemists in the field of materials science owing to their excellent photoconductivity, electroluminescence and fluorescence properties enabled by their rigid extended π-conjugation. Furthermore, tricyclic azaheteroaromatics are effective ligands for organometallic catalysis and a prominent drug discovery framework. Herein, we present the first one-step synthesis of a less-accessible tricyclic fluorophore comprising a 5,6-difluoro-2,9-diarylpyrimido[5,4-h]quinazoline core entailing the regiospecific tandem condensation of tetrafluoroterephthalonitrile and derivatives of benzamidine hydrochloride in the presence of potassium carbonate or cesium carbonate under mild conditions. Single-crystal X-ray diffractometry studies confirmed the structure of the 5,6-difluoro-2,9-diarylpyrimido[5,4-h]quinazolines, and various interactions such as π-π stacking. Spectroscopic measurements, including ultraviolet-visible (UV-vis) and fluorescence spectroscopy, of the synthesized pyrimido[5,4-h]quinazolines revealed that they have excellent fluorescence properties both in the solution and solid states, displaying red-shifted maximum fluorescence wavelengths in the solid state compared to those in the solution state. Density functional theory (DFT) calculations and electrochemical analyses revealed that the introduction of an electron-withdrawing group, such as a halogen, stabilized the energy levels. Thermogravimetric (TG) analysis indicated high decomposition temperatures for 5,6-difluoro-2,9-diarylpyrimido[5,4-h]quinazolines, confirming their favorable thermal stability. Finally, the halochromism of 5,6-difluoro-2,9-diarylpyrimido[5,4-h]quinazolines arising from the protonation of the amino group and/or pyrimidine backbone is described.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"121 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-05-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143945344","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
Photoinduced Regio- and Stereoselective Hydrotrifluoromethylation of Glycals with Langlois Reagent. Langlois试剂光诱导区域和立体选择性氢化三氟甲基化的研究。
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-05-13 DOI: 10.1021/acs.joc.5c00193
Tian Li,Miao Liu,Zhao-Xiang Luo,Xian-Jin Qin,Xin-Shan Ye,De-Cai Xiong
{"title":"Photoinduced Regio- and Stereoselective Hydrotrifluoromethylation of Glycals with Langlois Reagent.","authors":"Tian Li,Miao Liu,Zhao-Xiang Luo,Xian-Jin Qin,Xin-Shan Ye,De-Cai Xiong","doi":"10.1021/acs.joc.5c00193","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00193","url":null,"abstract":"Fluorination has demonstrated the potential to improve the physicochemical and enzymatic properties of carbohydrates. Hydrotrifluoromethylation is an emerging reaction to introduce trifluoromethyl groups. However, the hydrotrifluoromethylation of glycals has been challenging because of the lack of regioselectivity and stereoselectivity. Herein, we describe an efficient, highly selective, and broadly applicable photoinduced hydrotrifluoromethylation strategy of glycals using cost-effective sodium trifluoromethanesulfonate to give 1,2-dideoxy-2-trifluoromethyl sugars.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"4 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-05-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143945104","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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