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Biomimetic Catalytic Remote Desaturation of Aliphatic Alcohols
IF 5.2 1区 化学
Organic Letters Pub Date : 2024-12-23 DOI: 10.1021/acs.orglett.4c03623
Kaiming Zuo, Jing Zhu, Faral Akhtar, Phong Dam, Luis Miguel Azofra, Osama El-Sepelgy
{"title":"Biomimetic Catalytic Remote Desaturation of Aliphatic Alcohols","authors":"Kaiming Zuo, Jing Zhu, Faral Akhtar, Phong Dam, Luis Miguel Azofra, Osama El-Sepelgy","doi":"10.1021/acs.orglett.4c03623","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c03623","url":null,"abstract":"Herein we present photoinduced cobaloxime-catalyzed selective remote desaturation of aliphatic alcohols. This transformation, which proceeds efficiently at room temperature, facilitates the synthesis of valuable cyclic and acyclic allylic and homoallylic alcohols from readily available saturated aliphatic alcohols. Remarkably, this method obviates the need for external oxidants, noble metal catalysts, and phosphine ligands.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"13 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2024-12-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142874527","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
Glycosyl Radical-Based Synthesis of C-Alkyl Glycosides Bearing a Cyclopropane via a Deoxygenative Giese Addition–Reduction–Cyclization Cascade
IF 5.2 1区 化学
Organic Letters Pub Date : 2024-12-23 DOI: 10.1021/acs.orglett.4c04510
Jian-Yu Pang, Li-Min Feng, Wen-Feng Zhang, De-Yong Liu, Jing Wang, Ruo-Han Wei, Xiang-Guo Hu
{"title":"Glycosyl Radical-Based Synthesis of C-Alkyl Glycosides Bearing a Cyclopropane via a Deoxygenative Giese Addition–Reduction–Cyclization Cascade","authors":"Jian-Yu Pang, Li-Min Feng, Wen-Feng Zhang, De-Yong Liu, Jing Wang, Ruo-Han Wei, Xiang-Guo Hu","doi":"10.1021/acs.orglett.4c04510","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04510","url":null,"abstract":"We have developed a glycosyl radical-based synthesis of <i>C</i>-alkyl glycosides through a deoxygenative Giese addition–reduction–cyclization cascade, in which readily available 1-hydroxy carbohydrates serve as precursors for glycosyl radicals and aryl alkenes function as radical acceptors. This reaction not only provides an effective method for accessing a previously underexplored class of functionalized cyclopropanes but also enhances the application of Giese addition in the synthesis of <i>C</i>-alkyl glycosides by derivatizing the radical intermediate generated through polar cyclization to yield a cyclopropane.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"77 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2024-12-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142874604","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 Synthesis of Isoindolinone by Sequential Palladium-Catalyzed Aza-Heck/Suzuki Coupling Reaction
IF 5.2 1区 化学
Organic Letters Pub Date : 2024-12-23 DOI: 10.1021/acs.orglett.4c04239
Lei Wang, Wenyu Zhang, Shuaijie Wu, Qing Wu, Ying Han, Chao-Guo Yan, Guodong Zhang
{"title":"Enantioselective Synthesis of Isoindolinone by Sequential Palladium-Catalyzed Aza-Heck/Suzuki Coupling Reaction","authors":"Lei Wang, Wenyu Zhang, Shuaijie Wu, Qing Wu, Ying Han, Chao-Guo Yan, Guodong Zhang","doi":"10.1021/acs.orglett.4c04239","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04239","url":null,"abstract":"We present a tandem aza-Heck/Suzuki cross-coupling reaction of <i>O</i>-phenyl hydroxamic ethers with readily available arylboronic and alkenyl boronic acids. This protocol is enabled by a palladium catalyst paired with chiral phosphoramidite ligands, particularly under mild reaction conditions, yielding efficient and succinct synthetic routes to chiral isoindolinones with high enantioselectivity. Furthermore, this reaction exhibits excellent functional group compatibility and a rich diversity of subsequent transformations.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"85 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2024-12-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142874250","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
Site-Selective Electrophilic Trifluoromethylthiolation for the Synthesis of C5- or C7-SCF3-Substituted Indolines
IF 5.2 1区 化学
Organic Letters Pub Date : 2024-12-23 DOI: 10.1021/acs.orglett.4c04500
Xiaolong Wang, Yan Fu, Zhenshan Guo, Aijun Lin, Qingzhong Jia, Chunhua Han
{"title":"Site-Selective Electrophilic Trifluoromethylthiolation for the Synthesis of C5- or C7-SCF3-Substituted Indolines","authors":"Xiaolong Wang, Yan Fu, Zhenshan Guo, Aijun Lin, Qingzhong Jia, Chunhua Han","doi":"10.1021/acs.orglett.4c04500","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04500","url":null,"abstract":"We report herein an efficient and site-selective electrophilic trifluoromethylthiolation of indolines. In the absence of any catalyst or additive, C5-selective trifluoromethylthiolation could proceed at room temperature. With palladium used as the catalyst, the selectivity was reversed completely, giving C7-selecive trifluoromethylthiolated products. This reaction features good functional group tolerance, simple operation, mild conditions, and scale-up application. The potential utilities of the products were shown by further transformations.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"24 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2024-12-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142874516","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
Organocatalytic Enantioselective Arylation to Access Densely Aryl-Substituted P-Stereogenic Centers
IF 5.2 1区 化学
Organic Letters Pub Date : 2024-12-23 DOI: 10.1021/acs.orglett.4c03992
Hui-Lin Hu, Siqiang Fang, Xingjie Luo, Jiajia He, Jia-Hong Wu, Zhishan Su, Zhipeng Xu, Tianli Wang
{"title":"Organocatalytic Enantioselective Arylation to Access Densely Aryl-Substituted P-Stereogenic Centers","authors":"Hui-Lin Hu, Siqiang Fang, Xingjie Luo, Jiajia He, Jia-Hong Wu, Zhishan Su, Zhipeng Xu, Tianli Wang","doi":"10.1021/acs.orglett.4c03992","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c03992","url":null,"abstract":"Although methods for synthesizing chiral phosphorus scaffolds are available, the potential of this molecular chirality remains largely unexplored. Herein, we present a remote desymmetrization of prochiral biaryl phosphine oxides through an organocatalytic asymmetric arylation. This metal-free approach enables the efficient synthesis of a wide range of densely functionalized P(V)-stereogenic compounds with good to excellent yields and satisfactory enantioselectivities. Mechanistic studies reveal that hydrogen bonding and ion-pairing interactions are crucial for achieving precise stereocontrol in this transformation.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"31 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2024-12-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142874513","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 [2,3]-Sigmatropic Rearrangement of Azide–Ynamides via Selenium Ylides
IF 5.2 1区 化学
Organic Letters Pub Date : 2024-12-23 DOI: 10.1021/acs.orglett.4c04444
Chong-Yang Shi, Xuan Wang, Xin Liu, Zu-Hui Ai, Shuai Xiong, Long-Wu Ye, Bo Zhou, Xin-Qi Zhu
{"title":"Copper-Catalyzed [2,3]-Sigmatropic Rearrangement of Azide–Ynamides via Selenium Ylides","authors":"Chong-Yang Shi, Xuan Wang, Xin Liu, Zu-Hui Ai, Shuai Xiong, Long-Wu Ye, Bo Zhou, Xin-Qi Zhu","doi":"10.1021/acs.orglett.4c04444","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04444","url":null,"abstract":"A copper-catalyzed [2,3]-sigmatropic rearrangement of azide–ynamides via selenium ylides is disclosed, which leads to the practical and divergent synthesis of a variety of tricyclic heterocycles bearing a quaternary carbon stereocenter in generally moderate to excellent yields. Significantly, this method represents the first [2,3]-sigmatropic rearrangement of the selenium ylide based on alkynes and an unprecedented [2,3]-sigmatropic rearrangement via α-imino copper carbenes.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"475 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2024-12-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142874515","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
Photoredox Catalytic Defluoroalkylation of gem-Difluoroalkenes with Secondary N-Alkylanilines via C–F/C–H Coupling
IF 5.2 1区 化学
Organic Letters Pub Date : 2024-12-22 DOI: 10.1021/acs.orglett.4c04432
Haiyang Hu, Baokai Yang, Yongcan Liu, Wengang Xu, Congjian Xia, Guoqiang Xu, Mingbo Wu
{"title":"Photoredox Catalytic Defluoroalkylation of gem-Difluoroalkenes with Secondary N-Alkylanilines via C–F/C–H Coupling","authors":"Haiyang Hu, Baokai Yang, Yongcan Liu, Wengang Xu, Congjian Xia, Guoqiang Xu, Mingbo Wu","doi":"10.1021/acs.orglett.4c04432","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04432","url":null,"abstract":"To provide fluorinated allylamines, a visible-light photocatalytic C–F/C–H coupling of easily accessible <i>gem</i>-difluoroalkenes and secondary <i>N</i>-alkylanilines was described. The protocol proceeded under mild conditions, with excellent functional group compatibility and a broad scope including complex natural product derivatives, thus providing a green method for the preparation of high-value functionalized monofluoroalkenes. Mechanistic studies elucidated a photoredox catalyzed radical–radical coupling pathway.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"48 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2024-12-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142874606","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
Organophotoredox-Catalyzed Chemoselective Deprotection for Phenolic Ethers Driven by the Oxophilicity of Silicon
IF 5.2 1区 化学
Organic Letters Pub Date : 2024-12-22 DOI: 10.1021/acs.orglett.4c04357
Tanumoy Mandal, Malekul Islam, Sanju Das, Aznur Azim, Suman De Sarkar
{"title":"Organophotoredox-Catalyzed Chemoselective Deprotection for Phenolic Ethers Driven by the Oxophilicity of Silicon","authors":"Tanumoy Mandal, Malekul Islam, Sanju Das, Aznur Azim, Suman De Sarkar","doi":"10.1021/acs.orglett.4c04357","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04357","url":null,"abstract":"An organophotocatalyzed approach for the chemoselective dealkylation of phenols is developed. This method demonstrates exceptional selectivity toward the cleavage of phenolic ethers over equivalent aliphatic ethers and alkyl benzoates, presenting a broad range of functional group sustainability. This strategy also enables selective debenzylation of phenols in the presence of reduction-sensitive functional groups. Mechanistic studies and photophysical experiments provide evidence for the selective disintegration of C–O bonds through photo-oxidation, facilitated by the oxophilicity of silicon.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"53 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2024-12-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142874605","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
Unveiling the Phosphine-Mediated N-Transfer from Azide to Isocyanide en Route to Carbodiimides and 4-Imino-1,3,2-diazaphosphetidines 揭示膦介导的从叠氮化物到异氰酸酯再到碳化二亚胺和 4-氨基-1,3,2-二氮杂萘菲啶的 N-转移过程
IF 5.2 1区 化学
Organic Letters Pub Date : 2024-12-21 DOI: 10.1021/acs.orglett.4c03902
Aurelia Pastor, Carmen Lopez-Leonardo, Guillermo Cutillas-Font, Alberto Martinez-Cuezva, Marta Marin-Luna, Jose-Antonio Garcia-Lopez, Isabel Saura-Llamas, Mateo Alajarin
{"title":"Unveiling the Phosphine-Mediated N-Transfer from Azide to Isocyanide en Route to Carbodiimides and 4-Imino-1,3,2-diazaphosphetidines","authors":"Aurelia Pastor, Carmen Lopez-Leonardo, Guillermo Cutillas-Font, Alberto Martinez-Cuezva, Marta Marin-Luna, Jose-Antonio Garcia-Lopez, Isabel Saura-Llamas, Mateo Alajarin","doi":"10.1021/acs.orglett.4c03902","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c03902","url":null,"abstract":"Intramolecular reactions between isocyano and iminophosphorane functions yield species containing an embedded 1,3,2-diazaphosphetidine ring, as result of the [2 + 2] cycloaddition of the primary reactive product, the cyclic carbodiimide, with a second unit of reactant. DFT studies reveal a first rate-determining step entailing a [2 + 1] cycloaddition involving the isocyanide carbon atom and the P═N double bond, with the further intervention of a dipolar precursor of the intermediate carbodiimide. The 1,3,2-diazaphosphetidine ring of the final products is shown to be hydrolytically and thermally labile.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"55 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2024-12-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142867614","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
DMAP-Catalyzed [4 + 2] Annulation of Hex-5-en-2-ynoates with Electron-Poor Alkenes
IF 5.2 1区 化学
Organic Letters Pub Date : 2024-12-20 DOI: 10.1021/acs.orglett.4c03842
Dongqiu Li, Jiale Wu, LuLu Yang, Shuangshuang Cai, Yuhai Tang, Yang Li, Silong Xu
{"title":"DMAP-Catalyzed [4 + 2] Annulation of Hex-5-en-2-ynoates with Electron-Poor Alkenes","authors":"Dongqiu Li, Jiale Wu, LuLu Yang, Shuangshuang Cai, Yuhai Tang, Yang Li, Silong Xu","doi":"10.1021/acs.orglett.4c03842","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c03842","url":null,"abstract":"Herein, we report a DMAP-catalyzed [4 + 2] annulation reaction of hex-5-en-2-ynoates <b>1</b> with electron-poor alkenes <b>2</b>, which affords exocyclic olefinic cyclohexenes <b>3</b> in good yields and excellent regio-, diastereo-, and <i>E</i>/<i>Z</i> selectivities. Distinguished from previous allenoate- or alkynoate-based substrates, hex-5-en-2-ynoates <b>1</b> use the β- and ε-carbons for the bond formation, presenting new and regiodivergent C<sub>4</sub> synthons for Lewis base-catalyzed annulations.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"112 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2024-12-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142867615","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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