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Conjugated 1,8 and 1,6 Addition of Bis-Trimethylsilylketene Acetal to Activated p-Quinone Methides via Trifluoromethanesulfonic Anhydride
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-03-31 DOI: 10.1021/acs.joc.4c02852
Luis J. Benitez-Puebla, Ricardo Ballinas-Indili, Marcos Flores-Alamo, José M. Guevara-Vela, Tomas Rocha-Rinza, Saulo Rosales-Amezcua, Cecilio Alvarez-Toledano
{"title":"Conjugated 1,8 and 1,6 Addition of Bis-Trimethylsilylketene Acetal to Activated p-Quinone Methides via Trifluoromethanesulfonic Anhydride","authors":"Luis J. Benitez-Puebla, Ricardo Ballinas-Indili, Marcos Flores-Alamo, José M. Guevara-Vela, Tomas Rocha-Rinza, Saulo Rosales-Amezcua, Cecilio Alvarez-Toledano","doi":"10.1021/acs.joc.4c02852","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02852","url":null,"abstract":"In this work, we studied the conjugated additions of bis-trimethylsilylacetalketene acetals (bis-TMSKA) to <i>para</i>-quinone methides (<i>p</i>-QMs), which are one of the most explored molecules for the study of conjugated additions and gained significant attention in organic chemistry due to their versatile reactivity, particularly in Michael addition reactions. In this study, trifluoromethanesulfonic anhydride (Tf<sub>2</sub>O) was used as an activating agent for <i>p</i>-QMs, aiming to achieve 1,6-Michael addition products and the least reported 1,8-Michael addition with pyridine substituents. The reactivity of <i>p</i>-QMs derived from pyridine demonstrated distinct reaction pathways, leading to the formation of δ and γ lactones. The investigation also involved synthesizing a 1-indanone derived from the carboxylic acids obtained from the 1,6-addition.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"53 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-03-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143736932","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
Regioselective α-Allylation of Cyclic Allylborates with Allylic Bromides
IF 3.3 2区 化学
Journal of Organic Chemistry Pub Date : 2025-03-31 DOI: 10.1021/acs.joc.5c0013510.1021/acs.joc.5c00135
Go Yamagiwa, Hiroki Murata, Kazuhiko Semba and Tetsuaki Fujihara*, 
{"title":"Regioselective α-Allylation of Cyclic Allylborates with Allylic Bromides","authors":"Go Yamagiwa,&nbsp;Hiroki Murata,&nbsp;Kazuhiko Semba and Tetsuaki Fujihara*,&nbsp;","doi":"10.1021/acs.joc.5c0013510.1021/acs.joc.5c00135","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00135https://doi.org/10.1021/acs.joc.5c00135","url":null,"abstract":"<p >Allylic boron compounds are valuable nucleophiles for introducing allylic moieties into organic compounds. While numerous examples of γ-selective functionalization, such as the allylboration of carbonyl compounds, have been reported, α-selective carbon–carbon bond formation involving allylborates remains limited. In this study, α-selective allylation of cyclic allylborates was achieved using allylic bromides as carbon-based electrophiles. The reaction between cyclic allylborates and allylic bromides produced various allylboronates in moderate to good yields.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"90 14","pages":"5066–5069 5066–5069"},"PeriodicalIF":3.3,"publicationDate":"2025-03-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143814576","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
Mechanism and Origin of Nickel-Catalyzed Decarbonylative Construction of C(sp2)–C(sp3) Bonds from Carboxylic Acids and Their Derivatives
IF 3.3 2区 化学
Journal of Organic Chemistry Pub Date : 2025-03-31 DOI: 10.1021/acs.joc.4c0252110.1021/acs.joc.4c02521
Dan-Yan Tian, Wei-Peng Zhao and Zheng-Yang Xu*, 
{"title":"Mechanism and Origin of Nickel-Catalyzed Decarbonylative Construction of C(sp2)–C(sp3) Bonds from Carboxylic Acids and Their Derivatives","authors":"Dan-Yan Tian,&nbsp;Wei-Peng Zhao and Zheng-Yang Xu*,&nbsp;","doi":"10.1021/acs.joc.4c0252110.1021/acs.joc.4c02521","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02521https://doi.org/10.1021/acs.joc.4c02521","url":null,"abstract":"<p >Nickel-catalyzed arylation of carboxylic acids provides a ligand-controlled chemoselectivity-switchable method for the construction of C(sp<sup>2</sup>)–C(sp<sup>3</sup>) bonds. Here, we employed density functional theory to provide a detailed understanding of the mechanism and origin of nickel-catalyzed ligand-controlled carbonyl transformation. This reaction generates decarbonylation products through oxidative addition, activation of C–C bonds, decarbonylation, binding of alkyl radicals with Ni(III) complexes, and final reduction elimination step. The activation of C–C bonds in aromatic carboxylate esters is more favorable than C–O bond activation because of the interaction between the nickel catalyst and the π orbitals of the substrate’s aromatic moiety during C–C bond activation. The induction effect of the ligand and the carbonyl group together determines the transfer tendency of the carbonyl group.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"90 14","pages":"4808–4818 4808–4818"},"PeriodicalIF":3.3,"publicationDate":"2025-03-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143814636","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
Total Syntheses of Uvarindoles A and B, (±)-Pseudophrynaminol, and (±)-Pseudophrynamines 272A and 270 via Dearomative Indole Alkylation
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-03-31 DOI: 10.1021/acs.joc.5c00062
Raju Chouhan, Sajal Kumar Das
{"title":"Total Syntheses of Uvarindoles A and B, (±)-Pseudophrynaminol, and (±)-Pseudophrynamines 272A and 270 via Dearomative Indole Alkylation","authors":"Raju Chouhan, Sajal Kumar Das","doi":"10.1021/acs.joc.5c00062","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00062","url":null,"abstract":"Herein, we report the first total synthesis of alkaloid uvarindole B with an overall yield of 49% over five steps via double C3-alkylation of 5-bromoindole, Plancher rearrangement, and Negishi coupling as the key steps. We also disclose short total syntheses of uvarindole A, pseudophrynaminol, and pseudophrynamines 272A and 270 via dearomative indole alkylation.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"31 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-03-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143736933","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
Mechanism and Origin of Nickel-Catalyzed Decarbonylative Construction of C(sp2)–C(sp3) Bonds from Carboxylic Acids and Their Derivatives
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-03-31 DOI: 10.1021/acs.joc.4c02521
Dan-Yan Tian, Wei-Peng Zhao, Zheng-Yang Xu
{"title":"Mechanism and Origin of Nickel-Catalyzed Decarbonylative Construction of C(sp2)–C(sp3) Bonds from Carboxylic Acids and Their Derivatives","authors":"Dan-Yan Tian, Wei-Peng Zhao, Zheng-Yang Xu","doi":"10.1021/acs.joc.4c02521","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02521","url":null,"abstract":"Nickel-catalyzed arylation of carboxylic acids provides a ligand-controlled chemoselectivity-switchable method for the construction of C(sp<sup>2</sup>)–C(sp<sup>3</sup>) bonds. Here, we employed density functional theory to provide a detailed understanding of the mechanism and origin of nickel-catalyzed ligand-controlled carbonyl transformation. This reaction generates decarbonylation products through oxidative addition, activation of C–C bonds, decarbonylation, binding of alkyl radicals with Ni(III) complexes, and final reduction elimination step. The activation of C–C bonds in aromatic carboxylate esters is more favorable than C–O bond activation because of the interaction between the nickel catalyst and the π orbitals of the substrate’s aromatic moiety during C–C bond activation. The induction effect of the ligand and the carbonyl group together determines the transfer tendency of the carbonyl group.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"75 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-03-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143745265","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
Unified Total Syntheses of Anticancer Agent Nepetaefolin F and Indolosesquiterpenoids, Oridamycins A and B
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-03-30 DOI: 10.1021/acs.joc.5c00179
Ranjit Murmu, Debgopal Jana, Suman Noskar, Moumita Majhi, Alakesh Bisai
{"title":"Unified Total Syntheses of Anticancer Agent Nepetaefolin F and Indolosesquiterpenoids, Oridamycins A and B","authors":"Ranjit Murmu, Debgopal Jana, Suman Noskar, Moumita Majhi, Alakesh Bisai","doi":"10.1021/acs.joc.5c00179","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00179","url":null,"abstract":"The asymmetric total syntheses of triptobenzene L (<b>1a</b>), 4-<i>epi</i>-triptobenzene L (<b>1c</b>), nepetaefolin F (<b>1b</b>), and oridamycins A (<b>2c</b>) and B methyl ester (<b>2a</b>) have been accomplished through an enantioselective divergent approach from a highly functionalized common intermediate. A Lewis-acid-mediated highly regio- and diastereoselective epoxy-ene cyclization of (−)-<b>6</b> [92% ee] afforded the highly functionalized carbotricyclic core (+)-<b>5</b> [82%, dr &gt;20:1] sharing four contiguous stereogenic centers [out of which two are all-carbon quaternary stereogenic centers]. Efficient functionalization of the advanced intermediate enabled the successful asymmetric total syntheses of naturally occurring <i>anti</i>-cancer abietane diterpenoid, such as <b>1b</b> and indolosesquiterpenoids <b>2a</b> and <b>2c</b>.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"37 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-03-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143736383","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
Unified Total Syntheses of Anticancer Agent Nepetaefolin F and Indolosesquiterpenoids, Oridamycins A and B
IF 3.3 2区 化学
Journal of Organic Chemistry Pub Date : 2025-03-30 DOI: 10.1021/acs.joc.5c0017910.1021/acs.joc.5c00179
Ranjit Murmu, Debgopal Jana, Suman Noskar, Moumita Majhi and Alakesh Bisai*, 
{"title":"Unified Total Syntheses of Anticancer Agent Nepetaefolin F and Indolosesquiterpenoids, Oridamycins A and B","authors":"Ranjit Murmu,&nbsp;Debgopal Jana,&nbsp;Suman Noskar,&nbsp;Moumita Majhi and Alakesh Bisai*,&nbsp;","doi":"10.1021/acs.joc.5c0017910.1021/acs.joc.5c00179","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00179https://doi.org/10.1021/acs.joc.5c00179","url":null,"abstract":"<p >The asymmetric total syntheses of triptobenzene L (<b>1a</b>), 4-<i>epi</i>-triptobenzene L (<b>1c</b>), nepetaefolin F (<b>1b</b>), and oridamycins A (<b>2c</b>) and B methyl ester (<b>2a</b>) have been accomplished through an enantioselective divergent approach from a highly functionalized common intermediate. A Lewis-acid-mediated highly regio- and diastereoselective epoxy-ene cyclization of (−)-<b>6</b> [92% ee] afforded the highly functionalized carbotricyclic core (+)-<b>5</b> [82%, dr &gt;20:1] sharing four contiguous stereogenic centers [out of which two are all-carbon quaternary stereogenic centers]. Efficient functionalization of the advanced intermediate enabled the successful asymmetric total syntheses of naturally occurring <i>anti</i>-cancer abietane diterpenoid, such as <b>1b</b> and indolosesquiterpenoids <b>2a</b> and <b>2c</b>.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"90 14","pages":"4973–4992 4973–4992"},"PeriodicalIF":3.3,"publicationDate":"2025-03-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143814533","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
Sodium Poly(heptazine imide)-Enabled Oxytrifluoromethylation of Alkenes for the Synthesis of α-CF3 Ketones
IF 3.3 2区 化学
Journal of Organic Chemistry Pub Date : 2025-03-29 DOI: 10.1021/acs.joc.5c0011710.1021/acs.joc.5c00117
Chen Bao, Xinyu Zhu, Mengying Xu, Ming Hou, Peng Wang and Guanyinsheng Qiu*, 
{"title":"Sodium Poly(heptazine imide)-Enabled Oxytrifluoromethylation of Alkenes for the Synthesis of α-CF3 Ketones","authors":"Chen Bao,&nbsp;Xinyu Zhu,&nbsp;Mengying Xu,&nbsp;Ming Hou,&nbsp;Peng Wang and Guanyinsheng Qiu*,&nbsp;","doi":"10.1021/acs.joc.5c0011710.1021/acs.joc.5c00117","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00117https://doi.org/10.1021/acs.joc.5c00117","url":null,"abstract":"<p >This paper describes a NaPHI-catalyzed oxytrifluoromethylation of olefins under photoirradiation. The reaction is applicable for the synthesis of α-trifluoromethyl ketones, which could be structurally elaborated into an array of useful scaffolds. Mechanistic studies suggested that photoexcited NaPHI* could facilitate the formation of singlet <sup>1</sup>O<sub>2</sub> through an EnT process, thus enabling difunctionalization with trifluoromethyl radical and oxygen radical anion species.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"90 14","pages":"4954–4958 4954–4958"},"PeriodicalIF":3.3,"publicationDate":"2025-03-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143814502","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
Electro-Oxidative Three-Component Synthesis of 3,5-Disubstituted-1,2,4-Thiadiazoles from Amines, Amidines, and CS2
IF 3.3 2区 化学
Journal of Organic Chemistry Pub Date : 2025-03-29 DOI: 10.1021/acs.joc.4c0256910.1021/acs.joc.4c02569
Peng-Fei Huang*, Ying Peng, Jia-Le Fu, Bo Li, Quan Zhou and Yu Liu*, 
{"title":"Electro-Oxidative Three-Component Synthesis of 3,5-Disubstituted-1,2,4-Thiadiazoles from Amines, Amidines, and CS2","authors":"Peng-Fei Huang*,&nbsp;Ying Peng,&nbsp;Jia-Le Fu,&nbsp;Bo Li,&nbsp;Quan Zhou and Yu Liu*,&nbsp;","doi":"10.1021/acs.joc.4c0256910.1021/acs.joc.4c02569","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02569https://doi.org/10.1021/acs.joc.4c02569","url":null,"abstract":"<p >1,2,4-Thiadiazoles, a significant class of heterocyclic compounds, are widely found in biologically active molecules. Herein, we report a green electrochemical three-component reaction of amines, amidines, and CS<sub>2</sub> for the effective synthesis of 3,5-disubstituted-1,2,4-thiadiazoles under metal- and oxidant-free conditions. Both aliphatic and aryl amines are well-tolerated at room temperature in a simple undivided cell. A series of 1,2,4-thiadiazoles are prepared with excellent functional groups.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"90 14","pages":"4819–4828 4819–4828"},"PeriodicalIF":3.3,"publicationDate":"2025-03-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143814501","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
Electro-Oxidative Three-Component Synthesis of 3,5-Disubstituted-1,2,4-Thiadiazoles from Amines, Amidines, and CS2
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-03-29 DOI: 10.1021/acs.joc.4c02569
Peng-Fei Huang, Ying Peng, Jia-Le Fu, Bo Li, Quan Zhou, Yu Liu
{"title":"Electro-Oxidative Three-Component Synthesis of 3,5-Disubstituted-1,2,4-Thiadiazoles from Amines, Amidines, and CS2","authors":"Peng-Fei Huang, Ying Peng, Jia-Le Fu, Bo Li, Quan Zhou, Yu Liu","doi":"10.1021/acs.joc.4c02569","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02569","url":null,"abstract":"1,2,4-Thiadiazoles, a significant class of heterocyclic compounds, are widely found in biologically active molecules. Herein, we report a green electrochemical three-component reaction of amines, amidines, and CS<sub>2</sub> for the effective synthesis of 3,5-disubstituted-1,2,4-thiadiazoles under metal- and oxidant-free conditions. Both aliphatic and aryl amines are well-tolerated at room temperature in a simple undivided cell. A series of 1,2,4-thiadiazoles are prepared with excellent functional groups.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"72 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-03-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143734485","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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