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eEtherification: An Electrochemical Strategy toward the Synthesis of Sterically Hindered Dialkyl Ethers from Activated Alcohols
IF 5.2 1区 化学
Organic Letters Pub Date : 2024-12-17 DOI: 10.1021/acs.orglett.4c04093
Cyrille Kiaku, Simon Kaltenberger, Daniel Raydan, Valerio Morlacci, Bini Claringbold, Charles A. I. Goodall, Laura Palombi, Darren L. Poole, Kevin Lam
{"title":"eEtherification: An Electrochemical Strategy toward the Synthesis of Sterically Hindered Dialkyl Ethers from Activated Alcohols","authors":"Cyrille Kiaku, Simon Kaltenberger, Daniel Raydan, Valerio Morlacci, Bini Claringbold, Charles A. I. Goodall, Laura Palombi, Darren L. Poole, Kevin Lam","doi":"10.1021/acs.orglett.4c04093","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04093","url":null,"abstract":"Traditional etherification methods, although staples in synthetic chemistry, often fall short in the efficient construction of sterically hindered dialkyl ethers, especially under mild and practical conditions. Recent advances have attempted to address these limitations, typically relying on transition metal catalysts, external reductants, or harsh reaction conditions. In this work, we disclose a novel electrochemical approach that enables the synthesis of sterically hindered ethers from economically relevant and readily accessible alcohols without the need for sacrificial oxidants. Our protocol exploits mild conditions to generate reactive carbocations, which are subsequently captured by alcohol nucleophiles to yield the desired ethers. This method is cost-effective, practical, and broad in scope, providing a valuable addition to chemists’ synthetic toolkit for ether synthesis.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"115 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2024-12-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142833009","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
Radical α-C–H Alkylation and Heteroarylation of Benzyl Anilines Enabled by Organic Photoredox Catalysis
IF 5.2 1区 化学
Organic Letters Pub Date : 2024-12-17 DOI: 10.1021/acs.orglett.4c04278
Cheng Huang, Zhong-Ming Ye, Yu-Shu Qin, Gui-Ping You, Zhenhong Wei, Hu Cai
{"title":"Radical α-C–H Alkylation and Heteroarylation of Benzyl Anilines Enabled by Organic Photoredox Catalysis","authors":"Cheng Huang, Zhong-Ming Ye, Yu-Shu Qin, Gui-Ping You, Zhenhong Wei, Hu Cai","doi":"10.1021/acs.orglett.4c04278","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04278","url":null,"abstract":"A photocatalysis-involved α-amino radical provides an appealing approach for rapid construction of complex amine architectures. Reported herein is an organophotoredox catalytic approach to α-C–H alkylation and heteroarylation of benzyl anilines, which enables the introduction of valuable trifluoromethyl alcohol, chromanone, or pyridine motifs at the α position of amines. This protocol highlights metal-free, step and atom economies and broad substrate scopes (>80 examples). Control experiments and electron paramagnetic resonance spectroscopy identified the α-amino radical derived from the α-amino C–H bond.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"25 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2024-12-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142833011","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
Photoinduced Cross-Coupling of Trifluoromethylarenes with Heteroarenes via Unactivated C(sp3)–F and C(sp2)–H Selective Cleavage
IF 5.2 1区 化学
Organic Letters Pub Date : 2024-12-17 DOI: 10.1021/acs.orglett.4c04420
Jiyao Zhang, Yuxiang Zhang, Lebin Qian, Zhijun Zuo
{"title":"Photoinduced Cross-Coupling of Trifluoromethylarenes with Heteroarenes via Unactivated C(sp3)–F and C(sp2)–H Selective Cleavage","authors":"Jiyao Zhang, Yuxiang Zhang, Lebin Qian, Zhijun Zuo","doi":"10.1021/acs.orglett.4c04420","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04420","url":null,"abstract":"The installation of <i>gem</i>-difluoromethylene groups into two adjacent aryl groups is a formidable synthetic challenge despite their attractive structural, physical, and biochemical properties. Herein, we disclose a photoredox-catalyzed selective defluoroarylation of heteroarenes through inert C(sp<sup>3</sup>)–F and C(sp<sup>2</sup>)–H selective cleavage, which provides a straightforward route to access medicinally relevant aryl–heteroaryl or heteroaryl–heteroaryl difluoromethane scaffolds. Salient features of this reaction include readily accessible starting materials, metal-free conditions, and broad substrate scope.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"86 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2024-12-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142841825","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
N-Bridged BODIPY Dimers: Exploring the Electron-Rich and Electron-Poor Coupling Limit via Pyrrole and Pyridine Annulation N 桥接的 BODIPY 二聚体：通过吡咯和吡啶环化探索富电子和贫电子耦合极限
IF 5.2 1区 化学
Organic Letters Pub Date : 2024-12-17 DOI: 10.1021/acs.orglett.4c03890
Sebastian H. Röttger, Lukas J. Patalag, Heinrich F. von Köller, Julia Werthmüller, Anjuli J. Birk, Burkhard Butschke, Peter G. Jones, Daniel B. Werz
{"title":"N-Bridged BODIPY Dimers: Exploring the Electron-Rich and Electron-Poor Coupling Limit via Pyrrole and Pyridine Annulation","authors":"Sebastian H. Röttger, Lukas J. Patalag, Heinrich F. von Köller, Julia Werthmüller, Anjuli J. Birk, Burkhard Butschke, Peter G. Jones, Daniel B. Werz","doi":"10.1021/acs.orglett.4c03890","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c03890","url":null,"abstract":"<b>A</b> facile access to <i>N</i>-heteroaryl-fused bis-BODIPY scaffolds has been developed. A BODIPY dimer with an α,α-amine linker serves as a starting material to obtain pyrrole- and pyridine-fused BODIPYs, either by direct oxidation or by oxidative condensation with an aldehyde building block. Both species mark antipodal conjugative coupling conditions that result in distinct spectral outcomes. In stark contrast to the pyrrole fusion, pyridine-coupled species show unique panchromatic absorption profiles.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"52 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2024-12-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142841807","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
Late-Stage Tailoring Steps in the Biosynthesis of β-Rubromycin Involve Successive Terminal Oxidations, a Selective Hydroxyl Reduction, and Distinctive O-Methylations
IF 5.2 1区 化学
Organic Letters Pub Date : 2024-12-17 DOI: 10.1021/acs.orglett.4c03965
Liwei Yi, Sirun Yi, Yeji Wang, Jieqian Kong, Yi Xiong, Yusheng Zhou, Yanwen Duan, Xiangcheng Zhu
{"title":"Late-Stage Tailoring Steps in the Biosynthesis of β-Rubromycin Involve Successive Terminal Oxidations, a Selective Hydroxyl Reduction, and Distinctive O-Methylations","authors":"Liwei Yi, Sirun Yi, Yeji Wang, Jieqian Kong, Yi Xiong, Yusheng Zhou, Yanwen Duan, Xiangcheng Zhu","doi":"10.1021/acs.orglett.4c03965","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c03965","url":null,"abstract":"β-Rubromycin (<b>1</b>) has a unique O-methylated naphthoquinone moiety and is an efficient inhibitor of human telomerase. Through <i>in vivo</i> and <i>in vitro</i> investigations, we elucidated the biosynthetic tailoring steps of compound <b>1</b>, which involve the carboxyl terminal via successive oxidizations by RubU and RubO1/RubO2, O-methylation of the carboxyl terminal by RubX, and reduction of C-3′ hydroxyl by RubK. The final tautomerization of the naphthoquinone moiety is mediated by RubO, which anchors the transitional intermediate through O-methylation to form the naphthoquinone tautomer. The structure–activity relationship further revealed the significant influences of the terminal modification status on anticancer activities of rubromycins.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"10 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2024-12-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142841820","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 Catalytic Enantioselective Suzuki Coupling for the Modular Construction of Axially Chiral BODIPYs with Bright Solid-State Emission
IF 5.2 1区 化学
Organic Letters Pub Date : 2024-12-17 DOI: 10.1021/acs.orglett.4c04123
Jingjing Cao, Jin-Ping Zhang, Fan Zhang, Zhengxin Kang, Lijuan Jiao, Zhong-Yuan Li, Erhong Hao
{"title":"A Catalytic Enantioselective Suzuki Coupling for the Modular Construction of Axially Chiral BODIPYs with Bright Solid-State Emission","authors":"Jingjing Cao, Jin-Ping Zhang, Fan Zhang, Zhengxin Kang, Lijuan Jiao, Zhong-Yuan Li, Erhong Hao","doi":"10.1021/acs.orglett.4c04123","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04123","url":null,"abstract":"The development of chiral BODIPYs attracts remarkable interest due to their unique properties, structural diversity, and good photochemical stability, whereas achieving the construction of chiral BODIPYs maintains scarce. Herein, we present an enantioselective synthesis of axially chiral BODIPYs through Suzuki-Miyaura coupling. The newly synthesized chiral BODIPYs and the coassembly showed desirable photophysical properties, including high fluorescence quantum yields and intense CPL, both in solution and the solid state.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"48 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2024-12-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142841821","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
Regio- and Stereoselective Electro-Mediated Carboalkoxylation of 1,3-Dienes 1,3-Dienes 的区域和立体选择性电介导羰基氧合反应
IF 5.2 1区 化学
Organic Letters Pub Date : 2024-12-16 DOI: 10.1021/acs.orglett.4c03922
Ophélie Montiège, Marion Siccardi, Morgane Sanselme, Cédric Schneider, Jean-François Brière, Hélène Beucher
{"title":"Regio- and Stereoselective Electro-Mediated Carboalkoxylation of 1,3-Dienes","authors":"Ophélie Montiège, Marion Siccardi, Morgane Sanselme, Cédric Schneider, Jean-François Brière, Hélène Beucher","doi":"10.1021/acs.orglett.4c03922","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c03922","url":null,"abstract":"1,3-Dienes are versatile raw materials for building molecular complexity. We report herein mild conditions for the regio- and stereoselective [only the (<i>E</i>) isomer obtained] 1,4-carboalkoxylation of 1,3-dienes. This electrochemical multicomponent reaction provides an eco-efficient and straightforward access to a diverse range of (<i>E</i>)-polyfunctionalized allyl ether products, without requiring any metal catalyst.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"12 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2024-12-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142833004","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
Electrogenerated Lewis Acid-Catalyzed Claisen Rearrangement of Allyl Aryl Ethers
IF 5.2 1区 化学
Organic Letters Pub Date : 2024-12-16 DOI: 10.1021/acs.orglett.4c03928
Yuta Niki, Koichi Mitsudo, Eisuke Sato, Seiji Suga
{"title":"Electrogenerated Lewis Acid-Catalyzed Claisen Rearrangement of Allyl Aryl Ethers","authors":"Yuta Niki, Koichi Mitsudo, Eisuke Sato, Seiji Suga","doi":"10.1021/acs.orglett.4c03928","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c03928","url":null,"abstract":"Catalysts for Claisen rearrangement have been intensively studied to overcome the need for high temperature. However, previous studies have encountered challenges, such as the need for heating, a long reaction time, and/or the need for equivalent amounts of catalyst. In this study, we introduce an effective electrogenerated boron-based Lewis acid catalyst for the aromatic Claisen rearrangement, which proceeds in a few minutes at ambient temperature. Generation of the electrogenerated Lewis acid catalyst is discussed based on NMR analysis and DFT calculations.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"41 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2024-12-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142832654","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
Silver-Catalyzed Markovnikov Addition Hydrofunctionalization of Terminal Alkynes: Synthesis of N-Enoxyimides and Oximes
IF 5.2 1区 化学
Organic Letters Pub Date : 2024-12-16 DOI: 10.1021/acs.orglett.4c04180
Hafiz Noor, Shuwei Zhang, Xiaodong Jia, Pan Gao, Yu Yuan
{"title":"Silver-Catalyzed Markovnikov Addition Hydrofunctionalization of Terminal Alkynes: Synthesis of N-Enoxyimides and Oximes","authors":"Hafiz Noor, Shuwei Zhang, Xiaodong Jia, Pan Gao, Yu Yuan","doi":"10.1021/acs.orglett.4c04180","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04180","url":null,"abstract":"<i>N</i>-Enoxyimides are versatile and valuable synthetic synthons in modern organic synthesis and catalysis. Herein, a silver-catalyzed hydrooxyimidation of terminal alkynes that enables the synthesis of <i>N</i>-enoxyimides, has been demonstrated. The protocol features are simple, step- and atom-efficient, scalable, and exhibit a broad scope of functional group tolerance under mild conditions. A novel hydrolysis of the <i>N</i>-enoxyimides unexpectedly provides the corresponding aromatic oximes in 96% yield, showing the potential application of this strategy.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"20 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2024-12-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142833014","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
Aerobic Reconstruction of Amines to Amides: A C–N/C–C Bond Cleavage Approach
IF 5.2 1区 化学
Organic Letters Pub Date : 2024-12-16 DOI: 10.1021/acs.orglett.4c04366
Qinyue Tao, Yanling Zheng, Qiang Li, Yang Long, Jing Wang, Zewei Jin, Xiangge Zhou
{"title":"Aerobic Reconstruction of Amines to Amides: A C–N/C–C Bond Cleavage Approach","authors":"Qinyue Tao, Yanling Zheng, Qiang Li, Yang Long, Jing Wang, Zewei Jin, Xiangge Zhou","doi":"10.1021/acs.orglett.4c04366","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04366","url":null,"abstract":"Herein, an aerobic reconstruction of amines to amides via C(sp<sup>3</sup>)–N bond and C(sp<sup>2</sup>)–C(sp<sup>3</sup>) bond cleavage is described. This method features a metal-free reaction, insensitivity to oxygen or moisture, and ambient air as the terminal oxidant. Preliminary mechanistic studies suggest that the reaction pathway of amine oxidation, followed by imine exchange and Beckmann rearrangement, is involved.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"11 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2024-12-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142833018","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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