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Perfluoroalkyl Editing of Fluoroalkynes: Chemo-, Regio-, and Stereoselective Synthesis of (E)-(2-Amino-fluoroalkenyl)pyrimidines
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-02-26 DOI: 10.1021/acs.orglett.5c00381
Xiao-Ying Li, Ming-Yao Tang, Qian Tong, Danhua Ge, Mengtao Ma, Zhi-Liang Shen, Xue-Qiang Chu
{"title":"Perfluoroalkyl Editing of Fluoroalkynes: Chemo-, Regio-, and Stereoselective Synthesis of (E)-(2-Amino-fluoroalkenyl)pyrimidines","authors":"Xiao-Ying Li, Ming-Yao Tang, Qian Tong, Danhua Ge, Mengtao Ma, Zhi-Liang Shen, Xue-Qiang Chu","doi":"10.1021/acs.orglett.5c00381","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00381","url":null,"abstract":"A chemo-, regio-, and stereoselective condensation reaction of perfluoroalkyl alkynes (PFAAs), (CH<sub>2</sub>O)<sub>n</sub>, and (NH<sub>4</sub>)<sub>2</sub>CO<sub>3</sub> through the cleavage of five inert C(sp<sup>3</sup>)-F bonds at three distinct carbon sites, thereby establishing an unprecedented platform for synthesizing structurally unique (<i>E</i>)-(2-amino-fluoroalkenyl)pyrimidines, is first developed. Remarkably, this reaction features mild reaction conditions, good compatibility with various functional groups, excellent <i>E</i>-stereoselectivity, late-stage modification of complex molecules, scalability, and versatile synthetic transformations of the resulting heterocyclic compounds.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"18 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-02-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143496171","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
Photoinduced Reductive [4 + 2] Cycloaddition of Nitroarenes
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-02-26 DOI: 10.1021/acs.orglett.4c04657
Taiki Kaneko, Rin Ito, Toshitaka Okamura, Takaaki Sato
{"title":"Photoinduced Reductive [4 + 2] Cycloaddition of Nitroarenes","authors":"Taiki Kaneko, Rin Ito, Toshitaka Okamura, Takaaki Sato","doi":"10.1021/acs.orglett.4c04657","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04657","url":null,"abstract":"Direct C–N bond formation from nitroarenes is a valuable synthetic tool for quick access to aniline derivatives. Transformation via nitroso intermediates could be useful due to their unique properties, but the generation of nitrosoarenes in situ from nitroarenes is challenging due to the tendency for various side reactions. Herein we report the photoinduced reductive [4 + 2] cycloaddition of nitroarenes. The method begins with the photoinduced reduction of nitroarenes to give nitrosoarenes by hydrogen atom abstraction (HAA). The generated nitrosoarenes undergo a nitroso Diels–Alder (NDA) reaction. The key to success is the use of N-heterocyclic carbene (NHC) borane, which promotes efficient HAA, enabling the NDA reaction to proceed without the need for transition metals, strong bases, or elevated temperatures. The developed conditions allow high functional group tolerance, enabling late-stage functionalization and further derivatization of biologically active compounds.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"22 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-02-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143496169","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
Anionic Stereogenic-at-Cobalt(III) Complex-Enabled Asymmetric Oxidation of N,N-Dialkyl Sulfenamides
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-02-26 DOI: 10.1021/acs.orglett.4c04857
Yue Shen, Xiao-Bao Wu, Hua-Jie Jiang, Liu-Zhu Gong
{"title":"Anionic Stereogenic-at-Cobalt(III) Complex-Enabled Asymmetric Oxidation of N,N-Dialkyl Sulfenamides","authors":"Yue Shen, Xiao-Bao Wu, Hua-Jie Jiang, Liu-Zhu Gong","doi":"10.1021/acs.orglett.4c04857","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04857","url":null,"abstract":"An asymmetric oxidation of <i>N</i>,<i>N</i>-dialkyl sulfenamides is exhibited by using anionic stereogenic-at-cobalt(III) complexes as catalysts. This protocol provides an alternative approach to access a diverse set of chiral tertiary sulfinamides with high enantioselectivities (24 examples, up to 94:6 e.r.). Additionally, control experiments suggest that this protocol could be accomplished through a chiral cationic S(IV) intermediate.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"51 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-02-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143496168","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
Asymmetric Hydrogenation of Polysubstituted Isoquinolines with Chiral Boranes
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-02-26 DOI: 10.1021/acs.orglett.5c00272
Fuqu Zou, Xiangqing Feng, Haifeng Du
{"title":"Asymmetric Hydrogenation of Polysubstituted Isoquinolines with Chiral Boranes","authors":"Fuqu Zou, Xiangqing Feng, Haifeng Du","doi":"10.1021/acs.orglett.5c00272","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00272","url":null,"abstract":"This paper describes an asymmetric hydrogenation of 1,3-disubstituted isoquinolines catalyzed by chiral borane derived from chiral alkene, giving the desired <i>cis</i>-products in high yields with up to 96% ee. In particular, the asymmetric hydrogenation of challenging 1,3,4-trisubstituted isoquinolines could proceed smoothly to afford the corresponding products in high yields with moderate ee’s for the first time.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"6 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-02-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143496170","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 Dearomative para-/ortho-Cycloaddition Cascades of N-Allylanilines with 1,4-Enynes and CO via Skeletal Reorganization
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-02-25 DOI: 10.1021/acs.orglett.4c04520
Qi Xue, Yang Li, Ming Hu, Hu Cai, Jin-Heng Li
{"title":"Palladium-Catalyzed Dearomative para-/ortho-Cycloaddition Cascades of N-Allylanilines with 1,4-Enynes and CO via Skeletal Reorganization","authors":"Qi Xue, Yang Li, Ming Hu, Hu Cai, Jin-Heng Li","doi":"10.1021/acs.orglett.4c04520","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04520","url":null,"abstract":"A selectivity-control approach for palladium-catalyzed dearomative <i>para</i>-/<i>ortho</i>-cycloaddition cascades of aromatic compounds with 1,4-enynes and CO via a skeletal reorganization process to produce polycycle-fused bicyclo[2.2.2]octenes is reported. This mechanistically novel process depends on a skeletal reorganization that consists of a sequence of dearomative [4 + 2] <i>para</i>-cycloaddition, 3,3-Cope rearrangement, and carbon–carbon bond activation/[4 + 2] cycloaddition.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"9 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-02-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143486332","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
Near-Infrared Twisted Polycyclic Arene-Fused BisBODIPYs through a Tandem Inter- and Intramolecular Scholl Reaction
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-02-25 DOI: 10.1021/acs.orglett.5c00311
Huiquan Zuo, Qinghua Wu, Long Wang, Zhengxin Kang, Heng Li, Hua Wang, Xing Guo, Jiangang Gao, Erhong Hao, Lijuan Jiao
{"title":"Near-Infrared Twisted Polycyclic Arene-Fused BisBODIPYs through a Tandem Inter- and Intramolecular Scholl Reaction","authors":"Huiquan Zuo, Qinghua Wu, Long Wang, Zhengxin Kang, Heng Li, Hua Wang, Xing Guo, Jiangang Gao, Erhong Hao, Lijuan Jiao","doi":"10.1021/acs.orglett.5c00311","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00311","url":null,"abstract":"Five novel polyaromatic-ring-fused bisBODIPYs have been synthesized from corresponding readily available α-arylBODIPYs through a FeCl<sub>3</sub>-mediated tandem inter- and intramolecular oxidative aromatic coupling reaction. These resultant bisBODIPYs show twisted planar conformations, strong absorptions (ε up to 1.8 × 10<sup>5</sup> M<sup>–1</sup> cm<sup>–1</sup>), and good fluorescence emissions in the near-infrared region (NIR, 660–734 nm) and good intersystem crossing efficiencies (Φ<sub>Δ</sub> = 18.9% for dimer <b>2d</b> in toluene), demonstrating their promising potential applications as heavy-atom-free photosensitizers.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"26 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-02-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143486015","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
Stereoselective Synthesis of Biology-Oriented Pentacyclic Pyrrolo[2,1-a]isoquinoline Scaffolds by Photoredox-Induced Radical Annulations
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-02-25 DOI: 10.1021/acs.orglett.5c00277
Zi-Qi Yi, Wenhui Zhang, Bing Yi, Chang Liu, Yanjun Xie, Maoqing Li, Yi Xiong, Weidong Wu, Jian-Ping Tan
{"title":"Stereoselective Synthesis of Biology-Oriented Pentacyclic Pyrrolo[2,1-a]isoquinoline Scaffolds by Photoredox-Induced Radical Annulations","authors":"Zi-Qi Yi, Wenhui Zhang, Bing Yi, Chang Liu, Yanjun Xie, Maoqing Li, Yi Xiong, Weidong Wu, Jian-Ping Tan","doi":"10.1021/acs.orglett.5c00277","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00277","url":null,"abstract":"We report a visible-light photoredox-induced stereoselective radical 1,3-dipolar cycloaddition between tetrahydroisoquinolines and coumarin derivatives, providing a platform for the efficient synthesis of pseudo-natural-inspired fused pentacyclic scaffolds. Using this protocol, a diverse range of valuable fused pentacyclic pyrrolo[2,1-<i>a</i>]isoquinolines were efficiently obtained in moderate to good yields and excellent diastereoselectivities. Mechanistic investigations including radical control experiments and light on/off studies indicated that the reaction underwent a visible-light induced radical process. The insights gained from our studies are expected to advance general efforts toward the green synthesis of biology-oriented pseudo-natural products and heterocyclic skeletons.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"25 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-02-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143496173","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 Glycosylation Protocol Based on 1,4-Naphthoquinone-Derived Thioglycosides
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-02-25 DOI: 10.1021/acs.orglett.5c00473
Mengyu Li, Xi Xiang, Zijie Zhou, Xin Zhou, Meifang Yang, Yitian Zhao, Xiangwei Zheng, Houchao Tao
{"title":"Copper-Catalyzed Glycosylation Protocol Based on 1,4-Naphthoquinone-Derived Thioglycosides","authors":"Mengyu Li, Xi Xiang, Zijie Zhou, Xin Zhou, Meifang Yang, Yitian Zhao, Xiangwei Zheng, Houchao Tao","doi":"10.1021/acs.orglett.5c00473","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00473","url":null,"abstract":"We report a copper-catalyzed glycosylation protocol utilizing 2-(<i>para</i>-methoxyphenylethynyl)-1,4-naphthoquinone-3-thioglycosides (NQTs) as effective glycosyl donors. These novel donors, characterized by a naphthoquinone scaffold, enable rapid and efficient preparation through a one-pot, two-step synthesis. Additionally, they are efficiently activated by cost-effective Cu(II) salts, facilitating glycosylation with a broad range of substrates. The practicality of NQT donors is further demonstrated by their compatibility with latent-active glycosylation strategies and their applicability in the versatile one-pot synthesis of saccharides.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"51 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-02-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143496174","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
Access to Chiral Dihydro-1,4-Benzoxazine-2-Carboxylates through NHC-Catalyzed Dynamic Kinetic Resolution
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-02-25 DOI: 10.1021/acs.orglett.5c00119
Bin Liu, Qinqin Liu, Guanbin Wei, Zaihui Yang, Qing He, Rong-Hua Wang, Chao Yang, Tianyuan Zhang, Xiangkai Kong, Jiayu Huang, Weike Liao, Jianta Wang, Lei Tang
{"title":"Access to Chiral Dihydro-1,4-Benzoxazine-2-Carboxylates through NHC-Catalyzed Dynamic Kinetic Resolution","authors":"Bin Liu, Qinqin Liu, Guanbin Wei, Zaihui Yang, Qing He, Rong-Hua Wang, Chao Yang, Tianyuan Zhang, Xiangkai Kong, Jiayu Huang, Weike Liao, Jianta Wang, Lei Tang","doi":"10.1021/acs.orglett.5c00119","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00119","url":null,"abstract":"A chiral carbene-catalyzed dynamic kinetic resolution for the facile synthesis of enantioenriched dihydro-1,4-benzoxazine-2-carboxylates is disclosed. The reaction conditions are mild, and a diversity of substituents are well-tolerated in this transformation. In addition, our methodology also provides an efficient strategy for building chiral chromane-2-carboxylate and 2,3-dihydro-1,4-benzodioxane-2-carboxylate. The optically pure products generated from this protocol can be easily derived as the key intermediates of chiral drugs and bioactive molecules.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"28 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-02-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143496172","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
Sc(OTf)3-Catalyzed C–C Bond Cleavage of Unactivated Acylazaarenes with 1,2-Diamines to Afford Azaarenes and Imidazoles
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-02-25 DOI: 10.1021/acs.orglett.5c00026
Bo Pang, Hai-Long Xin, Jeesoo Choi, Hiroyuki Morimoto, Takashi Ohshima
{"title":"Sc(OTf)3-Catalyzed C–C Bond Cleavage of Unactivated Acylazaarenes with 1,2-Diamines to Afford Azaarenes and Imidazoles","authors":"Bo Pang, Hai-Long Xin, Jeesoo Choi, Hiroyuki Morimoto, Takashi Ohshima","doi":"10.1021/acs.orglett.5c00026","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00026","url":null,"abstract":"We report a method for cleaving the C(O)–sp<sup>2</sup>C bonds of unactivated acylazaarenes via benzimidazoline intermediates using a mild redox neutral catalytic system involving scandium triflate. This method avoids the need for preactivation or transition metal catalysts, enabling efficient C–C bond cleavage in a broad range of substrates, including 2-acylimidazoles, 2-acylpyridines, 2-acylpyrole, and even nonchelating 3-acylindole, in which direct C–C bond cleavage has not been previously achieved.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"5 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-02-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143486333","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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