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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
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
TBHP-Promoted Trifluoromethyl-difluoromethylthiolation of Unactivated Alkenes with CF3SO2Na and PhSO2SCF2H
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-02-25 DOI: 10.1021/acs.orglett.5c00146
Zengrui Liang, Wengui Wang, Shoufeng Wang
{"title":"TBHP-Promoted Trifluoromethyl-difluoromethylthiolation of Unactivated Alkenes with CF3SO2Na and PhSO2SCF2H","authors":"Zengrui Liang, Wengui Wang, Shoufeng Wang","doi":"10.1021/acs.orglett.5c00146","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00146","url":null,"abstract":"A TBHP-promoted trifluoromethyl-difluoromethylthiolation of alkenes was reported. Langlois’ reagent was used as a stable and inexpensive trifluoromethyl source. In the presence of TBHP, the trifluoromethyl radical generated reacted with alkenes, achieving a new alkyl radical, which could be trapped by PhSO<sub>2</sub>SCF<sub>2</sub>H, forming C–C and C–S bonds in one step and incorporating trifluoromethyl and difluoromethylthio groups. The mild conditions and broad functional group tolerance endowed the reaction with great potential in the field of pharmaceuticals and agrochemicals.","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":"143486334","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
Single-Atom Tuning of Pyridine-Strapped Pillar[5]arene Capsules for Specific Guest Binding
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-02-24 DOI: 10.1021/acs.orglett.5c00110
Araya Ruengsuk, Sutthipoj Vigromsitdet, Amporn Saekee, Pornnaphat Wichannananon, Tanagorn Sangtawesin, Mongkol Sukwattanasinitt, Jonggol Tantirungrotechai, David J. Harding, Thanthapatra Bunchuay
{"title":"Single-Atom Tuning of Pyridine-Strapped Pillar[5]arene Capsules for Specific Guest Binding","authors":"Araya Ruengsuk, Sutthipoj Vigromsitdet, Amporn Saekee, Pornnaphat Wichannananon, Tanagorn Sangtawesin, Mongkol Sukwattanasinitt, Jonggol Tantirungrotechai, David J. Harding, Thanthapatra Bunchuay","doi":"10.1021/acs.orglett.5c00110","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00110","url":null,"abstract":"Pyridine bis(carboxamide)-strapped pillar[5]arene capsules were synthesized with the serendipitous formation of macrotricyclic products. The structural integrity of the supramolecular capsules, determined by the specific orientation of a single nitrogen atom, controls the electronic properties of the confined binding cavity, facilitating length-selective recognition of aliphatic organic guests with nitrile, isocyanide, and amine functional groups with exceptional host–guest binding affinity and selectivity for 1,2-diaminoethane (<i>K</i><sub>a</sub> &gt; 10<sup>4</sup> M<sup>–1</sup>) in a polar organic solvent.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"17 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-02-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143477448","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
Gold-Catalyzed 1,2-Carboxyarylation of Alkenes
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-02-24 DOI: 10.1021/acs.orglett.5c00288
Tanmayee Nanda, Avishek Das, Prafulla Bera, Nitin T. Patil
{"title":"Gold-Catalyzed 1,2-Carboxyarylation of Alkenes","authors":"Tanmayee Nanda, Avishek Das, Prafulla Bera, Nitin T. Patil","doi":"10.1021/acs.orglett.5c00288","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00288","url":null,"abstract":"Herein, we disclose an unprecedented gold-catalyzed 1,2-carboxyarylation of alkenes through ligand-enabled Au(I)/Au(III) catalysis. Unlike other approaches for the arylative functionalization of C–C multiple bonds, attempts to utilize weak nucleophiles such as carboxylate anions were unsuccessful. The key to achieving this transformation is the use of a 1,3-diketone-appended alkene, which undergoes gold-catalyzed oxyarylation followed by retro-aldol reaction to afford the product. Detailed mechanistic investigations were conducted to support the proposed mechanism.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"50 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-02-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143477450","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
Enantioselective Organocatalytic Conjugate Addition of Malonates to β,β-Disubstituted β-Trifluoromethyl Enones under High Pressure
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-02-24 DOI: 10.1021/acs.orglett.5c00065
Alicja J. Połosak, Michał P. Głowacki, Piotr Kwiatkowski
{"title":"Enantioselective Organocatalytic Conjugate Addition of Malonates to β,β-Disubstituted β-Trifluoromethyl Enones under High Pressure","authors":"Alicja J. Połosak, Michał P. Głowacki, Piotr Kwiatkowski","doi":"10.1021/acs.orglett.5c00065","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00065","url":null,"abstract":"The first enantioselective Michael addition of malonates to acyclic β,β-disubstituted enones has been developed. Sterically hindered β-trifluoromethyl α,β-unsaturated 2-acyl thiazoles and benzothiazoles were found to be the most reactive groups of enones in the reaction catalyzed by bifunctional tertiary amine–thioureas (2–5 mol %). However, application of hyperbaric conditions (8–10 kbar) was required. The adducts containing quaternary stereogenic centers with a CF<sub>3</sub> group were obtained in high yields (vs &lt;1% at 1 bar) with enantiomeric excesses up to 95%.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"65 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-02-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143477444","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
Collective Total Synthesis of Four Ganoderma Meroterpenoids Based on an Intramolecular Aldol Strategy
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-02-24 DOI: 10.1021/acs.orglett.4c04756
Yasuhiro Meguro, Mari Oyake, Masaru Enomoto, Shigefumi Kuwahara
{"title":"Collective Total Synthesis of Four Ganoderma Meroterpenoids Based on an Intramolecular Aldol Strategy","authors":"Yasuhiro Meguro, Mari Oyake, Masaru Enomoto, Shigefumi Kuwahara","doi":"10.1021/acs.orglett.4c04756","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04756","url":null,"abstract":"The total synthesis of four <i>Ganoderma</i> meroterpenoids (lingzhiol, sinensilactam A, lingzhilactone B, and applanatumol I) has been accomplished from a known olefinic lactone in much shorter steps (4–8 steps) and markedly improved overall yields (15–27%) compared to previous syntheses. The key steps are highly regio- and diastereoselective intramolecular aldol reactions to prepare bicyclic lactone intermediates and a decarboxylative radical cyclization to install the unique tetracyclic ring system of lingzhiol.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"22 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-02-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143486336","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
Domino Synthesis of Thioindirubin via Aldol Condensation/C–S Cross-Coupling/Cyclization Reaction Using Xanthate as a Sulfur Surrogate
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-02-24 DOI: 10.1021/acs.orglett.4c04539
Palanisamy Soundarya, Sayan Pahan, Govindasamy Sekar
{"title":"Domino Synthesis of Thioindirubin via Aldol Condensation/C–S Cross-Coupling/Cyclization Reaction Using Xanthate as a Sulfur Surrogate","authors":"Palanisamy Soundarya, Sayan Pahan, Govindasamy Sekar","doi":"10.1021/acs.orglett.4c04539","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04539","url":null,"abstract":"Developing new types of molecular photoswitches with novel functionalities allows experts to advance their applications in biology, chemistry, and material sciences. Herein, we report an efficient synthetic protocol for the synthesis of thioindirubin derivatives from commercially available starting materials. This domino reaction proceeds through aldol condensation followed by intramolecular C–S bond formation and selective cyclization in a 5-<i>exo</i>-<i>trig</i> manner. Nuclear magnetic resonance studies suggest the ability to tune both isomerization directions upon irradiation with different ultraviolet and visible light (370–640 nm light-emitting diode). The newly reported hemithioindigo photoswitches have various applications in the areas of life science and material sciences.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"4 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-02-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143477446","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 Total Synthesis of Eremophilanolide Sesquiterpene Xylareremophil and Its Congeners
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-02-24 DOI: 10.1021/acs.orglett.5c00028
Hui-Bin Wang, Tian-Jie Ge, Xian-Tao An, Xin-Yu Liu, Le-Le Meng, Yu-Han Yang, Jun-Yi Zhou, Xian-He Zhao, Chun-An Fan
{"title":"Asymmetric Total Synthesis of Eremophilanolide Sesquiterpene Xylareremophil and Its Congeners","authors":"Hui-Bin Wang, Tian-Jie Ge, Xian-Tao An, Xin-Yu Liu, Le-Le Meng, Yu-Han Yang, Jun-Yi Zhou, Xian-He Zhao, Chun-An Fan","doi":"10.1021/acs.orglett.5c00028","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00028","url":null,"abstract":"The first asymmetric, protecting group free total synthesis of eremophilanolide sesquiterpenes, xylareremophil (<b>1</b>), 2α,3α-epoxymairetolide A (<b>2</b>), and 2,3-<i>seco</i>-2,3-olide-1-deoxygenmairetolide F (<b>3</b>), is concisely achieved with a longest linear route of five to eight steps, starting from the known (5<i>S</i>)-5,6-dimethyl-2-cyclohexenone as the chiral starting material. This synthetic approach mainly features an oxa-Pauson–Khand reaction of the highly functionalized chiral aldehyde precursor, forging a γ-butenolide-fused tricyclic core framework of eremophilanolides in a one-step manner. This study provides a novel strategic perspective for the divergent synthesis of the eremophilanolide sesquiterpenes.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"12 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-02-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143477531","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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