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Molecular Dynamics of the Davies Ambimodal C-H Functionalization/Cope Rearrangement Reaction. Davies Ambimodal C-H Functionalization/Cope Rearrangement Reaction 的分子动力学。
IF 3.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-11-19 DOI: 10.1021/acs.joc.4c01682
Yaling Zhang, Chaoqin Cao, Yuanbin She, Huw M L Davies, Yun-Fang Yang, K N Houk
{"title":"Molecular Dynamics of the Davies Ambimodal C-H Functionalization/Cope Rearrangement Reaction.","authors":"Yaling Zhang, Chaoqin Cao, Yuanbin She, Huw M L Davies, Yun-Fang Yang, K N Houk","doi":"10.1021/acs.joc.4c01682","DOIUrl":"https://doi.org/10.1021/acs.joc.4c01682","url":null,"abstract":"<p><p>The mechanism of the dirhodium-catalyzed combined C-H functionalization/Cope rearrangement (CH/Cope) reaction discovered by the Davies group has been investigated with density functional theory (DFT) calculations and quasi-classical molecular dynamics (MD) simulations. Computations from the Davies group previously showed that there is a post-transition state bifurcation leading to a direct CH reaction and also to the CH/Cope product. While this work was in preparation, the Tantillo group and the Ess group independently reported quantum mechanical and molecular dynamics studies on the dirhodium-tetracarboxylate-catalyzed diazoester CH/Cope and CH insertion reactions with 1,3-cyclohexadiene and 1,4-cyclohexadiene, respectively. The Tantillo group cited \"dynamic mismatching\" to explain the origins of the low yield of CH/Cope products in some experiments; the Ess group explained the origins of product selectivity from the perspective of TS vibrational modes and their synchronization that occurs at the entropic intermediates. We report quasi-classical trajectories for the reaction of the carbene with 1-methylcyclohexene that afford both the CH/Cope and C-H insertion products. After passing through the transition state that involves mostly hydrogen transfer, momentum drives the reaction trajectories toward the CH/Cope products.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":" ","pages":""},"PeriodicalIF":3.3,"publicationDate":"2024-11-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142666617","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Protecting Group Control of Hydroxyketone-Hemiketal Tautomeric Equilibrium Enables the Stereoselective Synthesis of a 1'-Azido C-Nucleoside. 保护基团对羟基酮-半金属同分异构平衡的控制实现了 1'-Azido C 核苷的立体选择性合成。
IF 3.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-11-19 DOI: 10.1021/acs.joc.4c01981
Subhankar Panda, Moyosore O Orimoloye, Tej Narayan Poudel, Steven De Jonghe, Dirk Jochmans, Johan Neyts, Courtney C Aldrich
{"title":"Protecting Group Control of Hydroxyketone-Hemiketal Tautomeric Equilibrium Enables the Stereoselective Synthesis of a 1<i>'</i>-Azido <i>C</i>-Nucleoside.","authors":"Subhankar Panda, Moyosore O Orimoloye, Tej Narayan Poudel, Steven De Jonghe, Dirk Jochmans, Johan Neyts, Courtney C Aldrich","doi":"10.1021/acs.joc.4c01981","DOIUrl":"https://doi.org/10.1021/acs.joc.4c01981","url":null,"abstract":"<p><p>The synthesis of 1<i>'</i>-azido <i>C</i>-nucleosides is described to expand the set of azide-functionalized nucleosides for bioorthogonal applications and as potential antiviral drugs. Lewis acid-promoted azidation of a nucleoside hemiketal resulted in the formation of a tetrazole through a Schmidt reaction manifold. Conformational control to prevent ring-chain tautomerism enabled efficient 1<i>'</i>-azidation with complete β-diastereoselectivity. The unique reactivity and further derivation of the 1<i>'</i>-azido <i>C</i>-nucleosides are also reported.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":" ","pages":""},"PeriodicalIF":3.3,"publicationDate":"2024-11-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142666620","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
C2-Arylated Indoles and Benzofurans through Formal (4 + 1) Annulation of N-Sulfonyl-2-aminobenzaldehydes and Salicylaldehyde Derivatives with Electron-Deficient Benzyl Chlorides. 通过 N-磺酰基-2-氨基苯甲醛和水杨醛衍生物与缺电子苄基氯的形式化 (4 + 1) 嵌合反应制备 C2-芳基吲哚和苯并呋喃。
IF 3.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-11-18 DOI: 10.1021/acs.joc.4c02231
Lillian A de Ceuninck van Capelle, Kimia Rahmannia, James M Macdonald, Christopher Richardson, Michael G Gardiner, John H Ryan, Rasool Babaahmadi, Steven M Wales, Christopher J T Hyland
{"title":"C2-Arylated Indoles and Benzofurans through Formal (4 + 1) Annulation of <i>N</i>-Sulfonyl-2-aminobenzaldehydes and Salicylaldehyde Derivatives with Electron-Deficient Benzyl Chlorides.","authors":"Lillian A de Ceuninck van Capelle, Kimia Rahmannia, James M Macdonald, Christopher Richardson, Michael G Gardiner, John H Ryan, Rasool Babaahmadi, Steven M Wales, Christopher J T Hyland","doi":"10.1021/acs.joc.4c02231","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02231","url":null,"abstract":"<p><p>A two-step formal (4 + 1) annulation-dehydration reaction offers a convenient route to C2-arylated indoles and benzofurans. This reaction exploits the bifunctional reactivity of electron-deficient benzyl chlorides with <i>N</i>-sulfonyl-2-aminobenzaldehydes or salicylaldehyde derivatives. The reaction tolerates both electron-withdrawing and donating groups on the substituted aldehydes, as well as variation of electron-withdrawing groups at the <i>para</i> position of the benzyl chloride reagent. This work also identifies interesting byproducts resulting from the self-reaction of these benzyl chlorides under basic conditions.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":" ","pages":""},"PeriodicalIF":3.3,"publicationDate":"2024-11-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142666504","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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 Sulfinamidines via Iron-Catalyzed Nitrene Transfer Reaction with Sulfenamides. 通过铁催化的腈与亚磺酰胺的转移反应合成亚磺酰胺。
IF 3.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-11-18 DOI: 10.1021/acs.joc.4c02286
Zhi-Kun Zhang, Yin Yuan, Huiling Peng, Yidan Han, Junliang Zhang, Junfeng Yang
{"title":"Synthesis of Sulfinamidines via Iron-Catalyzed Nitrene Transfer Reaction with Sulfenamides.","authors":"Zhi-Kun Zhang, Yin Yuan, Huiling Peng, Yidan Han, Junliang Zhang, Junfeng Yang","doi":"10.1021/acs.joc.4c02286","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02286","url":null,"abstract":"<p><p>An iron-catalyzed nitrene transfer reaction for the rapid synthesis of sulfinamidines from readily available sulfenamides is reported. This method features mild conditions, short reaction times, and a broad substrate scope, allowing the preparation of a variety of sulfinamidines in good to excellent yields. The synthetic utility of the sulfinamidine products was further demonstrated through their conversion to other valuable sulfur(VI) compounds, such as sulfondiimidoyl fluorides, sulfinamidiate esters, and sulfonimidamides. Preliminary efforts in the development of an asymmetric variant showed moderate enantioselectivity.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":" ","pages":""},"PeriodicalIF":3.3,"publicationDate":"2024-11-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142666622","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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 Regioselective C8-H Sulfoxamination of 1-Naphthylamine Derivatives with NH-Sulfoximines. 钴催化的 1-萘胺衍生物与 NH-亚磺酰亚胺的 Regioselective C8-H Sulfoxamination。
IF 3.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-11-18 DOI: 10.1021/acs.joc.4c02318
Nileshkumar B Rathod, Raj N Patel, Sachinkumar D Patel, Dharmik M Patel, Mahesh A Sonawane, Dinesh Gopichand Thakur, Subhash Chandra Ghosh
{"title":"Cobalt-Catalyzed Regioselective C8-H Sulfoxamination of 1-Naphthylamine Derivatives with NH-Sulfoximines.","authors":"Nileshkumar B Rathod, Raj N Patel, Sachinkumar D Patel, Dharmik M Patel, Mahesh A Sonawane, Dinesh Gopichand Thakur, Subhash Chandra Ghosh","doi":"10.1021/acs.joc.4c02318","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02318","url":null,"abstract":"<p><p>A simple cobalt-catalyzed, picolinamide-directed C8-H sulfoxamination of 1-naphthalamides with NH-sulfoximines has been developed. This cross-dehydrogenative C-H/N-H coupling reaction offers a facile route to N-arylated sulfoximines, exhibiting high yields, a broad substrate scope, and excellent functional group tolerance and scalability.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":" ","pages":""},"PeriodicalIF":3.3,"publicationDate":"2024-11-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142666506","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Development of a Highly Enantioselective Catalytic Di-π-methane Rearrangement. 开发一种高对映体选择性催化二-π-甲烷重排。
IF 3.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-11-17 DOI: 10.1021/acs.joc.4c02383
Samuel B Cahoon, Steven J Chapman, Tahoe A Fiala, Matthew J Genzink, Tehshik P Yoon
{"title":"Development of a Highly Enantioselective Catalytic Di-π-methane Rearrangement.","authors":"Samuel B Cahoon, Steven J Chapman, Tahoe A Fiala, Matthew J Genzink, Tehshik P Yoon","doi":"10.1021/acs.joc.4c02383","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02383","url":null,"abstract":"<p><p>The di-π-methane (DPM) rearrangement is an important organic photorearrangement that converts 1,4-diene-containing compounds to vinyl cyclopropanes, often resulting in extensive, synthetically valuable restructuring of the substrate's carbon framework. We investigated the influence of Lewis and Brønsted acids on the DPM rearrangement of dibenzobarrelenes. These studies have culminated in the identification of a dual chiral Brønsted acid-iridium photosensitizer system that enables the first highly enantioselective catalytic all-carbon DPM rearrangement.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":" ","pages":""},"PeriodicalIF":3.3,"publicationDate":"2024-11-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142646524","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Robust Organocatalytic Three-Component Approach to 1,3-Diarylallylidene Pyrazolones via Consecutive Double Condensation Reactions 通过连续双缩合反应制备 1,3-二芳基亚甲基吡唑酮的稳健有机催化三组分方法
IF 4.354 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-11-16 DOI: 10.1021/acs.joc.4c02273
Ashvani K. Patel, Sampak Samanta
{"title":"Robust Organocatalytic Three-Component Approach to 1,3-Diarylallylidene Pyrazolones via Consecutive Double Condensation Reactions","authors":"Ashvani K. Patel, Sampak Samanta","doi":"10.1021/acs.joc.4c02273","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02273","url":null,"abstract":"A robust pyrrolidine-BzOH salt-catalyzed one-pot three-component reaction involving 4-unsubstituted pyrazolones, aryl/heteroarylaldehydes, and aryl methyl ketones is reported for the first time. This catalytic process fortifies an efficient method, allowing for the practical synthesis of a wide array of synthetically useful 1,3-diarylallylidene pyrazolones in good to high yields exclusively in their single geometrical isomer forms. Furthermore, this catalyst facilitates a sequential double condensation reaction under thermal conditions, thereby enabling two consecutive C═C bonds through displacement of aryl groups. Moreover, this organocatalytic technique achieves a 100% carbon atom economy, marking a significant step forward toward efficient and sustainable synthesis.","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":"62 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2024-11-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142642974","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Lewis Acid Promotes Three-Component Cyclization to Construct Dithioxazole Derivatives 路易斯酸促进三组分环化以构建二硫恶唑衍生物
IF 4.354 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-11-16 DOI: 10.1021/acs.joc.4c01723
Kai Zou, Anquan Li, Yitong Chen, Gao Cao, Baofu Zhu
{"title":"Lewis Acid Promotes Three-Component Cyclization to Construct Dithioxazole Derivatives","authors":"Kai Zou, Anquan Li, Yitong Chen, Gao Cao, Baofu Zhu","doi":"10.1021/acs.joc.4c01723","DOIUrl":"https://doi.org/10.1021/acs.joc.4c01723","url":null,"abstract":"A simple and effective strategy for the construction of disulfide-substituted oxazole derivatives from amides, ynals, and acetyl disulfides via a Lewis acid-promoted three-component reaction has been reported. In addition, this reaction possesses other unique advantages, such as transition-metal-free catalysis, the production of disulfides, good functional group tolerance, and good regioselectivity.","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":"9 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2024-11-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142642612","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Chemoselective Dehydrogenation and Hetero-Arylation of Amides via Radical Translocation Enabled by Photoexcited Triplet Ketone Catalysis 通过光激发三重酮催化的自由基转移实现酰胺的化学选择性脱氢和异芳基化
IF 4.354 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-11-16 DOI: 10.1021/acs.joc.4c02060
Akash Bisoyi, Amit Behera, Alisha Rani Tripathy, Vijay Kumar Simhadri, Veera Reddy Yatham
{"title":"Chemoselective Dehydrogenation and Hetero-Arylation of Amides via Radical Translocation Enabled by Photoexcited Triplet Ketone Catalysis","authors":"Akash Bisoyi, Amit Behera, Alisha Rani Tripathy, Vijay Kumar Simhadri, Veera Reddy Yatham","doi":"10.1021/acs.joc.4c02060","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02060","url":null,"abstract":"We herein report the chemoselective dehydrogenation and heteroarylation of amides through photoexcited triplet ketone catalysis. Under mild reaction conditions, the generated aryl radical through the halogen atom transfer (XAT) process further undergoes an intramolecular 1,5-HAT event to generate an α-amido alkyl radical, which then intercepted with either cobalt or a reduced cyano arene radical leads to dehydrogenated and heteroarylated products, respectively, in good yields.","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":"13 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2024-11-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142642613","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
From Established to Emerging: Evolution of Cross-Coupling Reactions 从成熟到新兴：交叉偶联反应的演变
IF 3.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-11-15 DOI: 10.1021/acs.joc.4c0257310.1021/acs.joc.4c02573
Mark R. Biscoe, Josep Cornella, Dipannita Kalyani and Sharon Neufeldt*, 
{"title":"From Established to Emerging: Evolution of Cross-Coupling Reactions","authors":"Mark R. Biscoe,&nbsp;Josep Cornella,&nbsp;Dipannita Kalyani and Sharon Neufeldt*,&nbsp;","doi":"10.1021/acs.joc.4c0257310.1021/acs.joc.4c02573","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02573https://doi.org/10.1021/acs.joc.4c02573","url":null,"abstract":"","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":"89 22","pages":"16065–16069 16065–16069"},"PeriodicalIF":3.3,"publicationDate":"2024-11-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142640581","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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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