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Site-Selective Gold-Catalyzed Alkylation of α-Aminotropones with Allenes 金催化α-氨基托品与烯烃的位点选择性烷基化反应
IF 5.2 1区 化学
Organic Letters Pub Date : 2024-10-21 DOI: 10.1021/acs.orglett.4c03372
Giulio Gallorini, Sofia Kiriakidi, Sara Bellini, Carlos Silva López, Giulio Bertuzzi, Marco Bandini
{"title":"Site-Selective Gold-Catalyzed Alkylation of α-Aminotropones with Allenes","authors":"Giulio Gallorini, Sofia Kiriakidi, Sara Bellini, Carlos Silva López, Giulio Bertuzzi, Marco Bandini","doi":"10.1021/acs.orglett.4c03372","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c03372","url":null,"abstract":"The site-selective alkylation of α-aminotropones is effectively realized via gold(I)-catalyzed electrophilic activation of allenamides and allenyl ethers, yielding up to 85% in 30 examples. A dedicated and combined spectroscopic and computational investigation accounts for both chemo- and regioselective profiles of the protocol. New opportunities in the chemical space of tropone/tropolone derivatives are identified.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":null,"pages":null},"PeriodicalIF":5.2,"publicationDate":"2024-10-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142452382","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
Base-Controlled Chemodivergent [4 + 1] and [2 + 1]/[4 + 2] Annulations of o-Aminochalcones with γ-Bromocrotonates 邻氨基查耳酮与γ-溴巴豆酸盐的碱控化学歧化[4 + 1]和[2 + 1]/[4 + 2]嵌合反应
IF 5.2 1区 化学
Organic Letters Pub Date : 2024-10-21 DOI: 10.1021/acs.orglett.4c03187
Mengting Tan, Yunping Zheng, Sen Zhang, Hui Yao, Xin Yan, Xing Zhao, Mingguo Liu, Nianyu Huang, Nengzhong Wang
{"title":"Base-Controlled Chemodivergent [4 + 1] and [2 + 1]/[4 + 2] Annulations of o-Aminochalcones with γ-Bromocrotonates","authors":"Mengting Tan, Yunping Zheng, Sen Zhang, Hui Yao, Xin Yan, Xing Zhao, Mingguo Liu, Nianyu Huang, Nengzhong Wang","doi":"10.1021/acs.orglett.4c03187","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c03187","url":null,"abstract":"Controlling the selectivity of reactions is a significantly attractive strategy in synthetic organic chemistry. Herein, an efficient base-controlled chemodivergent domino reaction between <i>o</i>-aminochalcones and <i>γ-</i>bromocrotonates has been developed. A series of <i>cis</i>-2,3-disubstituted indolines and cyclopropane-fused tetrahydroquinolines were obtained via two pathways with a broad substrate scope in moderate to excellent yields under transition-metal-free conditions. It is noteworthy that the <i>γ-</i>bromocrotonates could be used as C1 or C2 synthons by modulating the base; in particular, the <i>γ-</i>bromocrotonates were used as both nucleophiles and electrophiles to generate cyclopropanes for the first time.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":null,"pages":null},"PeriodicalIF":5.2,"publicationDate":"2024-10-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142452386","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 2-Oxabicyclo[2.1.1]hexanes and their use in Scaffold Hopping 获取 2-氧杂双环[2.1.1]己烷及其在支架跳跃中的应用
IF 5.2 1区 化学
Organic Letters Pub Date : 2024-10-21 DOI: 10.1021/acs.orglett.4c02221
Olivier Lorthioir, Niall Anderson, Scott Boyd, Luca Carlino, Paul Davey, William Hodds, Megan Howard, Marika Lindhagen, Katie Proctor, Okky Dwichandra Putra, Theo Smith, Oliver Turner, Alfie Woodhouse, Millie Woodward
{"title":"Access to 2-Oxabicyclo[2.1.1]hexanes and their use in Scaffold Hopping","authors":"Olivier Lorthioir, Niall Anderson, Scott Boyd, Luca Carlino, Paul Davey, William Hodds, Megan Howard, Marika Lindhagen, Katie Proctor, Okky Dwichandra Putra, Theo Smith, Oliver Turner, Alfie Woodhouse, Millie Woodward","doi":"10.1021/acs.orglett.4c02221","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c02221","url":null,"abstract":"Saturated isosteres of the <i>ortho</i>-substituted benzene ring remain rare due to the paucity of methods to access complex bridged systems. Using blue-light-mediated [2 + 2] photocycloaddition chemistry, we have developed a quick and practical route to provide novel 2-oxabicyclo[2.1.1]hexanes from simple feedstock materials in only three steps. Matched pair analysis confirmed that this motif could prove useful in the future to the drug discovery community as a scaffold endowed with remarkable properties.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":null,"pages":null},"PeriodicalIF":5.2,"publicationDate":"2024-10-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142452161","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
Benzyl Alcohol Functionalization of [1.1.1]Propellane with Alkanes and Aldehydes 苄醇与烷烃和醛对 [1.1.1]Propellane 的官能化作用
IF 5.2 1区 化学
Organic Letters Pub Date : 2024-10-21 DOI: 10.1021/acs.orglett.4c03429
Fei Li, Jianyang Dong, Chenya Wang, Huijuan Liao, Jiayi Dang, Juan Zhou, Gang Li, Dong Xue
{"title":"Benzyl Alcohol Functionalization of [1.1.1]Propellane with Alkanes and Aldehydes","authors":"Fei Li, Jianyang Dong, Chenya Wang, Huijuan Liao, Jiayi Dang, Juan Zhou, Gang Li, Dong Xue","doi":"10.1021/acs.orglett.4c03429","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c03429","url":null,"abstract":"Bicyclo[1.1.1]pentanes (BCPs) play a crucial role in drug discovery research as C(sp<sup>3</sup>)-rich bioisosteres of benzene rings. However, the preparation of BCPs with strong alkane C(sp<sup>3</sup>)–H bonds has not been reported to date. In this study, we reported a method for light-induced benzyl alcohol functionalization of [1.1.1]propellane with aliphatic hydrocarbons (which have not previously been explored for this purpose) and aldehydes under metal- and photocatalyst-free conditions. The BCP products could be transformed into various useful derivatives, demonstrating the utility of the method. Notably, we achieved the synthesis of functionalized BCPs with simple alkanes.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":null,"pages":null},"PeriodicalIF":5.2,"publicationDate":"2024-10-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142452383","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
Cobalt-Catalyzed Three-Component Alkyl Arylation of Acrylates with Alkyl Iodides and Aryl Grignard Reagents 钴催化烷基碘化物和芳基格氏试剂对丙烯酸酯的三组分烷基芳基化反应
IF 5.2 1区 化学
Organic Letters Pub Date : 2024-10-21 DOI: 10.1021/acs.orglett.4c03453
Lei Xu, Fan Zhang, Yan-En Wang, Congcong Bai, Dan Xiong, Jianyou Mao
{"title":"Cobalt-Catalyzed Three-Component Alkyl Arylation of Acrylates with Alkyl Iodides and Aryl Grignard Reagents","authors":"Lei Xu, Fan Zhang, Yan-En Wang, Congcong Bai, Dan Xiong, Jianyou Mao","doi":"10.1021/acs.orglett.4c03453","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c03453","url":null,"abstract":"A highly regioselective cobalt-catalyzed three-component alkyl arylation of acrylates with alkyl iodides and aryl Grignard reagents has been established. The reaction efficiently provides an alternative strategy for the construction of α-aryl esters with a broad substrate scope and good yields under mild conditions. The practical applicability of this protocol is shown by the scaled-up reaction and further transformations of the products. In addition, the preliminary mechanistic explorations demonstrated that the alkyl radicals generated by the efficient cobalt catalysis are instantaneously added to the acrylates to finally afford the desired products.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":null,"pages":null},"PeriodicalIF":5.2,"publicationDate":"2024-10-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142452388","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
Electrochemical Synthesis of C(sp3)-Rich Heterocycles via Mesolytic Cleavage of Anodically Generated Aromatic Radical Cations 通过阳极生成的芳香族自由基阳离子的介解裂解电化学合成富 C(sp3)杂环
IF 5.2 1区 化学
Organic Letters Pub Date : 2024-10-21 DOI: 10.1021/acs.orglett.4c03091
Hussain A. Maashi, Abdulrahman H. Husayni, Kharou M, Michael E. Reid, James Harnedy, Ethan C. Herneman, Marc Pera-Titus, Louis C. Morrill
{"title":"Electrochemical Synthesis of C(sp3)-Rich Heterocycles via Mesolytic Cleavage of Anodically Generated Aromatic Radical Cations","authors":"Hussain A. Maashi, Abdulrahman H. Husayni, Kharou M, Michael E. Reid, James Harnedy, Ethan C. Herneman, Marc Pera-Titus, Louis C. Morrill","doi":"10.1021/acs.orglett.4c03091","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c03091","url":null,"abstract":"Herein we report an electrochemical deconstructive functionalization approach for the synthesis of C(sp<sup>3</sup>)-rich heterocycles. The reaction proceeds <i>via</i> the mesolytic cleavage of anodically generated aromatic radical cations and the trapping of formed carbocation intermediates with internal nucleophiles. The method has been demonstrated across various arylalcohol substrates to access a diverse range of C(sp<sup>3</sup>)-rich heterocycles including tetrahydrofuran, tetrahydropyran, and pyrrolidine scaffolds (26 examples). The electrochemical method was demonstrated on a 5 mmol scale <i>via</i> single pass continuous flow, which utilized lower supporting electrolyte concentration and exhibited increased productivity in relation to the batch process.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":null,"pages":null},"PeriodicalIF":5.2,"publicationDate":"2024-10-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142452165","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 Heck/C(sp2)–H Activation/Decarboxylative Cyclization of C2-Tethered Indoles 钯催化的 C2 系吲哚的 Dearomative Heck/C(sp2)-H活化/脱羧环化反应
IF 5.2 1区 化学
Organic Letters Pub Date : 2024-10-21 DOI: 10.1021/acs.orglett.4c03663
Shuyi Guo, Wenbo Deng, Xiaochang Xiao, Jingru Xia, Xing Yang, Yun Liang, Yuan Yang
{"title":"Palladium-Catalyzed Dearomative Heck/C(sp2)–H Activation/Decarboxylative Cyclization of C2-Tethered Indoles","authors":"Shuyi Guo, Wenbo Deng, Xiaochang Xiao, Jingru Xia, Xing Yang, Yun Liang, Yuan Yang","doi":"10.1021/acs.orglett.4c03663","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c03663","url":null,"abstract":"Until now, palladium-catalyzed dearomative Heck reactions of indoles were largely limited to β-H elimination and nucleophilic capture of the transient alkyl-Pd(II) species. Herein, we disclose a novel palladium-catalyzed dearomative Heck/C(sp<sup>2</sup>)–H activation/decarboxylative cyclization of C2-tethered indoles. In this protocol, the alkyl-Pd(II) species formed by dearomatization of C2-tethered indoles is not terminated by common β-H elimination or nucleophilic capture, but rather generates <i>C</i>,<i>C</i>-palladacycle via C–H activation. The latter is intercepted by α-bromoacrylic acids to produce pentacyclic and heptacyclic fused indolines.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":null,"pages":null},"PeriodicalIF":5.2,"publicationDate":"2024-10-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142452367","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
Organophotocatalytic Regioselective Silylation/Germylation and Cascade Cyclization of N-Alkenyl α-CF3 Acrylamides: Access to Densely Functionalized 4-Pyrrolin-2-ones 有机光催化 N-烯基 α-CF3 丙烯酸酰胺的区域选择性硅烷化/革兰氏化和级联环化：获得致密官能化的 4-吡咯啉-2-酮
IF 5.2 1区 化学
Organic Letters Pub Date : 2024-10-21 DOI: 10.1021/acs.orglett.4c03427
Kalu Ram Bajya, Shivam Kumar Maurya, Sermadurai Selvakumar
{"title":"Organophotocatalytic Regioselective Silylation/Germylation and Cascade Cyclization of N-Alkenyl α-CF3 Acrylamides: Access to Densely Functionalized 4-Pyrrolin-2-ones","authors":"Kalu Ram Bajya, Shivam Kumar Maurya, Sermadurai Selvakumar","doi":"10.1021/acs.orglett.4c03427","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c03427","url":null,"abstract":"We report an organophotoredox-catalyzed silylation/germylation cascade cyclization of <i>N</i>-alkenyl α-CF<sub>3</sub> acrylamides under mild conditions. <i>N</i>-Aminopyridinium salts act as hydrogen atom transfer reagents under photoredox catalysis in the generation of silyl and germyl radicals. An array of silyl- and germyl-substituted 3-CF<sub>3</sub>-4-pyrrolin-2-one derivatives were constructed in a shorter reaction time with low catalyst loading in good to excellent yields at room temperature. Importantly, this protocol is amenable to the late-stage diversification of bioactive molecules, as well as to large-scale synthesis.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":null,"pages":null},"PeriodicalIF":5.2,"publicationDate":"2024-10-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142452365","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
Photosensitized Three-Component Carboimination of Alkenes Based on the Relay of Oxy Radicals to Carbon Radicals 基于氧自由基到碳自由基中继的光敏化三组分烯烃羧化反应
IF 5.2 1区 化学
Organic Letters Pub Date : 2024-10-21 DOI: 10.1021/acs.orglett.4c03247
Ai-Lian Wang, Hao-Wen Jiang, Xu-Yan Han, Yong-Chun Luo, Peng-Fei Xu
{"title":"Photosensitized Three-Component Carboimination of Alkenes Based on the Relay of Oxy Radicals to Carbon Radicals","authors":"Ai-Lian Wang, Hao-Wen Jiang, Xu-Yan Han, Yong-Chun Luo, Peng-Fei Xu","doi":"10.1021/acs.orglett.4c03247","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c03247","url":null,"abstract":"Here, we present a metal-free photosensitized three-component reaction for the carboimination of alkenes based on oxime carbonates. Homolysis of oxime carbonates via light-mediated energy transfer enables the simultaneous generation of iminyl radicals and alkoxycarbonyloxyl radicals. The alkoxycarbonyloxyl and alkoxy radicals can act as an effective hydrogen atom transfer reagent, abstracting hydrogen atoms from alkanes and aldehydes, silanes, and phosphine oxide. This strategy exhibits broad functional group tolerance under mild reaction conditions, further broadening the diversity of alkene carboimination.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":null,"pages":null},"PeriodicalIF":5.2,"publicationDate":"2024-10-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142452369","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
Activity and Biocatalytic Potential of an Indolylamide Generating Thioesterase 吲哚酰胺生成硫酯酶的活性和生物催化潜力
IF 5.2 1区 化学
Organic Letters Pub Date : 2024-10-21 DOI: 10.1021/acs.orglett.4c03648
Weimao Zhong, Zachary L. Budimir, Lucas O. Johnson, Elizabeth I. Parkinson, Vinayak Agarwal
{"title":"Activity and Biocatalytic Potential of an Indolylamide Generating Thioesterase","authors":"Weimao Zhong, Zachary L. Budimir, Lucas O. Johnson, Elizabeth I. Parkinson, Vinayak Agarwal","doi":"10.1021/acs.orglett.4c03648","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c03648","url":null,"abstract":"The chemical synthesis of <i>N</i>-acyl indoles is hindered by the poor nucleophilicity of indolic nitrogen, necessitating the use of strongly basic reaction conditions that encumber elaboration of highly functionalized scaffolds. Herein, we describe the total chemoenzymatic synthesis of the bulbiferamide natural products by the biochemical activity reconstitution of a nonribosomal peptide synthetase assembly line-derived (NRPS-derived) thioesterase that neatly installs the macrocyclizing indolylamide. The enzyme represents a starting point for biocatalytic access to macrocyclic indolylamide peptides and natural products.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":null,"pages":null},"PeriodicalIF":5.2,"publicationDate":"2024-10-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142452368","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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