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Copper-Catalyzed Stereoconvergent 1,4-Protosilylation of E/Z Dienes 铜催化E/Z二烯的立体聚合1,4-原硅基化反应
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-06-02 DOI: 10.1021/acs.orglett.5c01841
Longtao Huang, Yueyuan Wang, Min Gao, Shizhao Xu, Luqing Lin
{"title":"Copper-Catalyzed Stereoconvergent 1,4-Protosilylation of E/Z Dienes","authors":"Longtao Huang, Yueyuan Wang, Min Gao, Shizhao Xu, Luqing Lin","doi":"10.1021/acs.orglett.5c01841","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c01841","url":null,"abstract":"The conversion of <i>E</i>/<i>Z</i> isomeric olefin mixtures to a singular product is both significant and challenging. In this study, we present a copper-catalyzed stereoconvergent 1,4-protosilylation of <i>E</i>/<i>Z</i> conjugated diene mixtures, yielding allylic silanes with exclusive 1,4-regioselectivity and a <i>Z</i> configuration. Density functional theory (DFT) calculations indicate stereoconvergent 1,4-protosilylation through Zimmerman–Traxler transition states during the protonation step, leading to the formation of the final <i>Z</i> isomer, allylic silane.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"37 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-06-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144192990","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
Triphenylene Diazocines: Butterfly-Type Rigid Photoswitches with Annulated Aromatic Ring Systems and Increased Switching Amplitude 三苯基重氮嘧啶：具有环芳香环系统和增加开关振幅的蝴蝶型刚性光开关
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-06-02 DOI: 10.1021/acs.orglett.5c01398
Artjom Businski, Daniel Hugenbusch, Thuy C. Ta, Ramina Tayaran, Lara Unterriker, Jan-Simon von Glasenapp, Christian Näther, Rainer Herges
{"title":"Triphenylene Diazocines: Butterfly-Type Rigid Photoswitches with Annulated Aromatic Ring Systems and Increased Switching Amplitude","authors":"Artjom Businski, Daniel Hugenbusch, Thuy C. Ta, Ramina Tayaran, Lara Unterriker, Jan-Simon von Glasenapp, Christian Näther, Rainer Herges","doi":"10.1021/acs.orglett.5c01398","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c01398","url":null,"abstract":"Azobenzenes are arguably the most frequently used photoswitches, but systems in which the benzene units are replaced by larger π systems are rare. Azonaphthalene is known, but the next higher homologue azoanthracene already undergoes irreversible intramolecular cycloaddition during photoisomerization. Such side reactions are not possible with rigid diazocines. In the present work, we have succeeded in integrating triphenylene groups into diazocines, making them the azo switches with the largest aromatic, annulated ring systems published to date. Both the unsubstituted system and several derivatives are easy to access. The extension of the π systems results in a larger molecular switching amplitude compared to parent diazocine, which should lead to better force transmission to the environment in material applications. The switching wavelengths are shifted bathochromically into the visible range, although the photostationary equilibria are decreased. Potential applications include switchable liquid crystals, mechanophores, photoactuators, and many other responsive materials. Particularly noteworthy is the 4-fold substitution of the system, which allows incorporation into larger systems, e.g. as multifunctional cross-linkers in polymers or as building blocks in COFs and MOFs.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"37 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-06-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144192979","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
EDA Complex-Mediated Aerobic Three-Component CDC Reactions of Quinoxalinones under Visible-Light Irradiation 可见光下EDA复合物介导喹啉酮类化合物需氧三组分CDC反应
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-06-02 DOI: 10.1021/acs.orglett.5c01704
Xiaoyuan Wan, Richang Wen, Yi Fang, Huawen Huang, Guo-Jun Deng
{"title":"EDA Complex-Mediated Aerobic Three-Component CDC Reactions of Quinoxalinones under Visible-Light Irradiation","authors":"Xiaoyuan Wan, Richang Wen, Yi Fang, Huawen Huang, Guo-Jun Deng","doi":"10.1021/acs.orglett.5c01704","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c01704","url":null,"abstract":"A visible-light-induced Minisci-type three-component aerobic cross-dehydrogenative coupling (CDC) reaction of quinoxalinones with styrenes and acetophenones is described. The catalytic electron donor–acceptor (EDA) complexation of quinoxalinones with TMSCl is found to be the key for oxygen activation, which initiates the oxidative radical formation of acetophenones under photocatalyst-free conditions. This three-component protocol provides facile and efficient access to structurally valuable highly functionalized quinoxalinones with generally high chemoselectivity and moderate to good yields.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"29 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-06-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144192986","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
A Unified Strategy for Transition-Metal-Free Synthesis of Benzothienopyridines, Benzoselenopyridines, and Benzotelluropyridines and Related Analogues 无过渡金属合成苯并噻吩吡啶、苯并硒代吡啶、苯并telluropyridine及相关类似物的统一策略
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-06-02 DOI: 10.1021/acs.orglett.5c01557
Zhaoyue Wen, Jianlian Wu, Chun Wang, Bingjie Shen, Mingyue Fu, Xinni Zheng, Cheng Lu, Wei Chen, Tie-Gen Chen
{"title":"A Unified Strategy for Transition-Metal-Free Synthesis of Benzothienopyridines, Benzoselenopyridines, and Benzotelluropyridines and Related Analogues","authors":"Zhaoyue Wen, Jianlian Wu, Chun Wang, Bingjie Shen, Mingyue Fu, Xinni Zheng, Cheng Lu, Wei Chen, Tie-Gen Chen","doi":"10.1021/acs.orglett.5c01557","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c01557","url":null,"abstract":"A transition-metal-free, unified synthetic approach has been developed for the efficient construction of benzothienopyridines, benzoselenopyridines, and benzotelluropyridines. This versatile methodology facilitates the formation of C–S, C–Se, and C–Te bonds through the cyclization reaction of readily available dihalogenated pyridyl biaryls with chalcogen sources (thiourea, elemental sulfur, selenium, or tellurium). Significantly, the derivatized products exhibit promising potential as building blocks for benzochalcogenophene-fused pyridine architectures and functional materials for organic optoelectronic applications, particularly in organic light-emitting diodes.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"47 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-06-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144192982","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
Dynamic Kinetic Asymmetric P–C Coupling of Secondary Phosphine Oxides with Alkenyl Iodides 二次膦氧化物与烯基碘化物的动态动力学不对称P-C偶联
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-06-02 DOI: 10.1021/acs.orglett.5c01664
Si-Mu Ren, Wen-Jun Yang, Kang Ding, Jie Kang, Jia-Xin Zou, Bo Su
{"title":"Dynamic Kinetic Asymmetric P–C Coupling of Secondary Phosphine Oxides with Alkenyl Iodides","authors":"Si-Mu Ren, Wen-Jun Yang, Kang Ding, Jie Kang, Jia-Xin Zou, Bo Su","doi":"10.1021/acs.orglett.5c01664","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c01664","url":null,"abstract":"Transition metal-catalyzed enantioselective P–C bond-forming reactions between racemic secondary phosphine oxides (SPOs) and various electrophiles have emerged as powerful strategies for accessing P-chiral compounds. However, most reported transformations proceeded via kinetic resolution of SPOs, inherently limiting efficiency. In contrast, dynamic kinetic asymmetric coupling enables full conversion of racemic SPOs─offering a more effective pathway─yet such methods remain rare. Herein, we report the first dynamic kinetic asymmetric P–C coupling of SPOs with alkenyl iodides. This transformation, enabled by a copper catalyst bearing a novel chiral 1,2-diamine ligand, affords a broad range of P-chiral tertiary phosphine oxides in good yields and with high enantioselectivity.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"36 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-06-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144192993","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
Catalytic Asymmetric Intramolecular Domino Allylic O-Alkylation/Allylic Dearomatization of Allyl Aryl Ethers 催化分子内不对称多米诺烯丙基o -烷基化/烯丙基芳基醚脱芳化
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-06-02 DOI: 10.1021/acs.orglett.5c01540
Yun-Qiao Zhang, Ying-Long Li, Ke-Xu Wang, Dong-Chao Wang, Hai-Ming Guo
{"title":"Catalytic Asymmetric Intramolecular Domino Allylic O-Alkylation/Allylic Dearomatization of Allyl Aryl Ethers","authors":"Yun-Qiao Zhang, Ying-Long Li, Ke-Xu Wang, Dong-Chao Wang, Hai-Ming Guo","doi":"10.1021/acs.orglett.5c01540","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c01540","url":null,"abstract":"An intramolecular asymmetric allylic O-alkylation/allylic dearomative spirocyclization cascade has been successfully developed with allyl aryl ethers. In the presence of palladium and a phosphoramidite ligand, a series of spirocyclohexadienones with an exocyclic double bond were obtained in up to 98% yield with 98% ee. The asymmetric allylic alkylation mechanism was elucidated through control experiments. In addition, scale-up of the reaction and further transformations of the spirocyclic products were also performed, demonstrating the potential application of this method.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"1 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-06-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144192981","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
Isolation of Noncrystalline Compounds via Adsorption on a Solid Support 固体载体吸附分离非晶体化合物
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-06-02 DOI: 10.1021/acs.orglett.5c01715
Patrick J. Moon, Joshua R. Belfield, Patrick S. Fier
{"title":"Isolation of Noncrystalline Compounds via Adsorption on a Solid Support","authors":"Patrick J. Moon, Joshua R. Belfield, Patrick S. Fier","doi":"10.1021/acs.orglett.5c01715","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c01715","url":null,"abstract":"Herein is described a method for the isolation of noncrystalline compounds via adsorption on a solid support. A range of compounds that present as neat oils can be isolated as free-flowing processable solids, including the direct isolation of products from crude reaction streams. This approach was successfully implemented on a multi-kilogram scale for the isolation of a linker fragment as part of an antibody–drug conjugate (ADC) program. This strategy provides a viable alternative in cases where traditional crystallization approaches prove particularly challenging or a through process is not an option.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"50 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-06-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144192987","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
Synthesis of Rhodocorane L Using Gold-Catalyzed Dearomative Spirocyclization 金催化脱芳螺旋环化法制备红杜鹃烷L
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-06-02 DOI: 10.1021/acs.orglett.5c01802
Emily A. Shimizu, Scott D. Rychnovsky
{"title":"Synthesis of Rhodocorane L Using Gold-Catalyzed Dearomative Spirocyclization","authors":"Emily A. Shimizu, Scott D. Rychnovsky","doi":"10.1021/acs.orglett.5c01802","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c01802","url":null,"abstract":"Reported herein is the first total synthesis of the acorane-type terpenoid rhodocorane L, isolated from the fungus <i>Rhodotus palmatus</i>. This unique tricyclic scaffold containing a spiro[4.5] bicycle has antifungal activity. Key steps include diastereoselective cuprate addition, gold-catalyzed dearomative spirocyclization, and intramolecular aldol. This is the first time that a catalyst-controlled asymmetric dearomative spirocyclization has been utilized in a total synthesis. Rhodocorane L was synthesized in 17 steps, as the longest linear sequence.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"13 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-06-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144192989","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
Expanding the Diversity of the Terpene Skeleton and Structure through Identification of Noncanonical Class IE and IF Terpene Synthase-Formed Products 通过鉴定非规范类IE和IF萜烯合酶形成的产物扩大萜烯骨架和结构的多样性
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-06-02 DOI: 10.1021/acs.orglett.5c01879
Tohru Abe, Tohru Taniguchi, Daijiro Ueda, Takashi Abe, Tsutomu Sato
{"title":"Expanding the Diversity of the Terpene Skeleton and Structure through Identification of Noncanonical Class IE and IF Terpene Synthase-Formed Products","authors":"Tohru Abe, Tohru Taniguchi, Daijiro Ueda, Takashi Abe, Tsutomu Sato","doi":"10.1021/acs.orglett.5c01879","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c01879","url":null,"abstract":"Noncanonical class IE and IF terpene synthases have recently been discovered from bacterial genomes through the nonsequence-similarity-based method: protein-structural-model-based genome mining. This study identified the class IE product as a new diterpene comprising the first hydrocarbon skeleton among all terpenoids. The skeleton with a 6/6/6-fused tricyclic structure and six methyl groups could be synthesized through an unprecedented terpene-forming reaction. The class IF product was identified as a new brasilane-type sesquiterpene.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"134 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-06-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144192992","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
cis-Diphosphine Ethene Ligand-Ni Complex Catalyzed C-P Cross-Coupling of Aryl Chlorides 顺式二膦乙烯配体- ni配合物催化芳酰氯C-P交叉偶联
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-06-02 DOI: 10.1021/acs.orglett.5c01596
Yumeng Wu, Zhe Tang, Xiaoli Li, Xulu Lv, Jinkui Chai, Fengqian Zhao, Junliang Wu
{"title":"cis-Diphosphine Ethene Ligand-Ni Complex Catalyzed C-P Cross-Coupling of Aryl Chlorides","authors":"Yumeng Wu, Zhe Tang, Xiaoli Li, Xulu Lv, Jinkui Chai, Fengqian Zhao, Junliang Wu","doi":"10.1021/acs.orglett.5c01596","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c01596","url":null,"abstract":"Nickel complexes supported by <i>cis</i>-diphosphine ethene ligands were synthesized and employed in the C-P coupling reaction of aryl chlorides. The rigid five-membered-ring structure formed by bisphosphine ligands with olefinic backbones and nickel may be crucial for facilitating the reductive elimination step in the catalytic cycle. The steric hindrance and electronic properties of these ligands have also been shown to have a significant effect on the rate and extent of the reaction. A series of aryl chlorides can be smoothly converted to the corresponding trisubstituted phosphine oxides with disubstituted phosphine oxides, as well as dialkyl phosphites, under mild conditions. The reaction system also showed good compatibility with heterocyclic structures. In addition, this air-stable and easy-to-handle nickel complex has demonstrated application potential in the synthesis of pharmaceutical molecules.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"59 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-06-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144192983","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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