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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
Oxygen Migration–Defluorination Strategy Enables the Aminocarbonylation of Enaminones with o-Aminobenzamides and CF2Br2
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-02-24 DOI: 10.1021/acs.orglett.5c00695
Wanqing Zuo, Renhua Zheng, Yinghong Huang, Xiao Geng, Lingling Zuo, Lei Wang
{"title":"Oxygen Migration–Defluorination Strategy Enables the Aminocarbonylation of Enaminones with o-Aminobenzamides and CF2Br2","authors":"Wanqing Zuo, Renhua Zheng, Yinghong Huang, Xiao Geng, Lingling Zuo, Lei Wang","doi":"10.1021/acs.orglett.5c00695","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00695","url":null,"abstract":"The development of different concept approaches and user-friendly carbonyl surrogates for aminocarbonylation is highly desirable. Herein, we report the photocatalytic aminocarbonylation of enaminones with easily available <i>o</i>-aminobenzamides and CF<sub>2</sub>Br<sub>2</sub> through an oxygen migration–defluorination strategy. The reaction features switchable transformation for the construction of carbamoyl-substituted enaminones and enol products and allows the expedient synthesis of fully substituted maleimides under mild reaction conditions.","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":"143486337","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
Optimizing Solid-Phase Protein Synthesis Using CPG-2000 and a Nickel-Cleavable SNAC-tag Linker
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-02-23 DOI: 10.1021/acs.orglett.5c00109
Jianyi Han, Bobo Dang
{"title":"Optimizing Solid-Phase Protein Synthesis Using CPG-2000 and a Nickel-Cleavable SNAC-tag Linker","authors":"Jianyi Han, Bobo Dang","doi":"10.1021/acs.orglett.5c00109","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00109","url":null,"abstract":"Solid-phase chemical ligation (SPCL) is a powerful method for simplifying protein synthesis but faces challenges with orthogonal protection strategies, suboptimal solid supports, and limited cleavable linkers. In this study, we optimized SPCL by combining low-loading controlled-pore glass (CPG-2000) with a nickel-cleavable SNAC-tag linker. This system enabled the successful assembly of five peptide fragments and the efficient synthesis of a 131-amino-acid de novo protein, achieving a 25% yield.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"27 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-02-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143477708","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 Regioselective 1,4-Sulfonyl Indolylation of 1,3-Dienes with Sulfonyl Chloride and Indoles
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-02-22 DOI: 10.1021/acs.orglett.5c00245
Pu Chen, Lin Tian, Xiaochen Ji, Guo-Jun Deng, Huawen Huang
{"title":"Copper-Catalyzed Regioselective 1,4-Sulfonyl Indolylation of 1,3-Dienes with Sulfonyl Chloride and Indoles","authors":"Pu Chen, Lin Tian, Xiaochen Ji, Guo-Jun Deng, Huawen Huang","doi":"10.1021/acs.orglett.5c00245","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00245","url":null,"abstract":"A copper-based catalytic system has been described to enable the efficient 1,4-sulfonylindolylation of 1,3-dienes with sulfonyl chloride and indoles. This protocol offers a practical method for the synthesis of allylsulfone-containing indole derivatives with a broad range of compatible functionalities and excellent chemo- and regioselectivities. Mechanistic studies suggest that the copper catalyst plays the dual role of initiating sulfonyl radicals and prompting indole coupling in this conjugated diene-selective 1,4-difunctionalization strategy.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"82 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-02-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143470678","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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