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Optimized Monomer-Based Synthesis of Poly-N-amino Peptides 基于单体优化的聚n -氨基肽合成
IF 3.3 2区 化学
Journal of Organic Chemistry Pub Date : 2025-04-20 DOI: 10.1021/acs.joc.5c0024710.1021/acs.joc.5c00247
Avraz F. Anwar,  and , Juan R. Del Valle*, 
{"title":"Optimized Monomer-Based Synthesis of Poly-N-amino Peptides","authors":"Avraz F. Anwar,&nbsp; and ,&nbsp;Juan R. Del Valle*,&nbsp;","doi":"10.1021/acs.joc.5c0024710.1021/acs.joc.5c00247","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00247https://doi.org/10.1021/acs.joc.5c00247","url":null,"abstract":"<p >We report an optimized protocol for the solid-phase synthesis of backbone-N-aminated peptides. Electrophilic N-amination of amino acid zwitterions provides crude α-hydrazino acids that can be used directly in SPPS. <i>In situ</i> formation of Fmoc-protected amino acid chlorides with Ghosez’s reagent enables base-free couplings to α-hydrazino acids on an automated system. TFA-free cleavage and global deprotection affords poly-N-amino peptides in high crude purity and in a fraction of the time required by previously reported methods.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"90 17","pages":"6084–6089 6084–6089"},"PeriodicalIF":3.3,"publicationDate":"2025-04-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143894156","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
Rh-Catalyzed Synthesis of Isobenzofurans via Donor/Donor-Type Metal Carbenoids and Their [4 + 2] Cycloaddition 铑催化供体/供体型金属类碳化合物合成异苯并呋喃及其[4 + 2]环加成
IF 3.3 2区 化学
Journal of Organic Chemistry Pub Date : 2025-04-20 DOI: 10.1021/acs.joc.5c0033910.1021/acs.joc.5c00339
Naoki Morita, Shinnosuke Yoshikawa, Eisuke Ota and Junichiro Yamaguchi*, 
{"title":"Rh-Catalyzed Synthesis of Isobenzofurans via Donor/Donor-Type Metal Carbenoids and Their [4 + 2] Cycloaddition","authors":"Naoki Morita,&nbsp;Shinnosuke Yoshikawa,&nbsp;Eisuke Ota and Junichiro Yamaguchi*,&nbsp;","doi":"10.1021/acs.joc.5c0033910.1021/acs.joc.5c00339","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00339https://doi.org/10.1021/acs.joc.5c00339","url":null,"abstract":"<p >A rhodium-catalyzed synthesis of isobenzofurans via donor- and donor-type metal carbenoids has been developed. Nosylhydrazones were used as carbene precursors, generating rhodium carbenoid species under basic conditions. These intermediates underwent intramolecular cyclization with ester groups to afford isobenzofurans, which subsequently participated in a highly <i>endo</i>-selective [4 + 2] cycloaddition with maleimides and other dienophiles. The reaction exhibited a broad substrate scope, accommodating various ester and aryl substituents while maintaining excellent regio- and stereoselectivity. Mechanistic studies, including control experiments, NMR analysis, and computational calculations, revealed that the reaction proceeds through a rhodium carbenoid intermediate, leading to the formation of isobenzofuran prior to cycloaddition. The <i>endo</i>-selectivity was found to originate from the difference in activation energies between the transition states, as supported by computational studies. Additionally, the isolation of the diazo intermediate and its direct conversion to isobenzofuran confirmed the stepwise nature of the transformation. This study expands the utility of donor- and donor-type carbenoids in organic synthesis, demonstrating their effectiveness in constructing highly reactive isobenzofurans under mild conditions.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"90 17","pages":"5986–5999 5986–5999"},"PeriodicalIF":3.3,"publicationDate":"2025-04-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143894157","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
Mn(acac)3/Hydrazide-Catalyzed Aerobic Oxidative Cross-Dehydrogenative Couplings of 1,2,3,4-Tetrahydroisoquinolines and Their Mechanistic Studies Mn(acac)3/肼催化1,2,3,4-四氢异喹啉的好氧交叉脱氢偶联及其机理研究
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-04-20 DOI: 10.1021/acs.joc.5c00296
Ga Young Kim, Sehee Park, Gayeong Park, Yeongyeong Kang, Hyungjun Kim, Jinho Kim
{"title":"Mn(acac)3/Hydrazide-Catalyzed Aerobic Oxidative Cross-Dehydrogenative Couplings of 1,2,3,4-Tetrahydroisoquinolines and Their Mechanistic Studies","authors":"Ga Young Kim, Sehee Park, Gayeong Park, Yeongyeong Kang, Hyungjun Kim, Jinho Kim","doi":"10.1021/acs.joc.5c00296","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00296","url":null,"abstract":"Aerobic oxidative cross-dehydrogenative couplings of 1,2,3,4-tetrahydroisoquinolines were developed using a Mn(acac)<sub>3</sub> and ethyl 2-(4-nitrophenyl)hydrazine-1-carboxylate cocatalytic system. Nucleophiles, including nitroalkanes, dialkyl malonates, acetophenones, indoles, phosphonates, and phosphine oxides, were successfully employed to produce α-functionalized 1,2,3,4-tetrahydroisoquinolines. Control experiments revealed that radical species are not involved in the mechanism. Additionally, <sup>1</sup>H NMR and HRMS analyses in the stoichiometric reaction identified an aminal structure as a crucial intermediate. Computational studies further support the plausibility of a hydride transfer process in the oxidation of 1,2,3,4-tetrahydroisoquinolines instead of the triazane pathway, which was predominantly proposed in the DEAD-mediated reaction.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"26 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-04-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143853593","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
Mn(acac)3/Hydrazide-Catalyzed Aerobic Oxidative Cross-Dehydrogenative Couplings of 1,2,3,4-Tetrahydroisoquinolines and Their Mechanistic Studies Mn(acac)3/肼催化1,2,3,4-四氢异喹啉的好氧交叉脱氢偶联及其机理研究
IF 3.3 2区 化学
Journal of Organic Chemistry Pub Date : 2025-04-20 DOI: 10.1021/acs.joc.5c0029610.1021/acs.joc.5c00296
Ga Young Kim, Sehee Park, Gayeong Park, Yeongyeong Kang, Hyungjun Kim* and Jinho Kim*, 
{"title":"Mn(acac)3/Hydrazide-Catalyzed Aerobic Oxidative Cross-Dehydrogenative Couplings of 1,2,3,4-Tetrahydroisoquinolines and Their Mechanistic Studies","authors":"Ga Young Kim,&nbsp;Sehee Park,&nbsp;Gayeong Park,&nbsp;Yeongyeong Kang,&nbsp;Hyungjun Kim* and Jinho Kim*,&nbsp;","doi":"10.1021/acs.joc.5c0029610.1021/acs.joc.5c00296","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00296https://doi.org/10.1021/acs.joc.5c00296","url":null,"abstract":"<p >Aerobic oxidative cross-dehydrogenative couplings of 1,2,3,4-tetrahydroisoquinolines were developed using a Mn(acac)<sub>3</sub> and ethyl 2-(4-nitrophenyl)hydrazine-1-carboxylate cocatalytic system. Nucleophiles, including nitroalkanes, dialkyl malonates, acetophenones, indoles, phosphonates, and phosphine oxides, were successfully employed to produce α-functionalized 1,2,3,4-tetrahydroisoquinolines. Control experiments revealed that radical species are not involved in the mechanism. Additionally, <sup>1</sup>H NMR and HRMS analyses in the stoichiometric reaction identified an aminal structure as a crucial intermediate. Computational studies further support the plausibility of a hydride transfer process in the oxidation of 1,2,3,4-tetrahydroisoquinolines instead of the triazane pathway, which was predominantly proposed in the DEAD-mediated reaction.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"90 17","pages":"5966–5972 5966–5972"},"PeriodicalIF":3.3,"publicationDate":"2025-04-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143894154","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
A Unified Strategy for the Synthesis of Diverse Bicyclo[2.2.2]octadiene Ligands 合成多种双环[2.2.2]辛二烯配体的统一策略
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-04-19 DOI: 10.1021/acs.joc.5c00115
Wen-Tao Chen, Wen-Cai Luo, Jun-Ting Liang, Yu-Tao He, Ya-Jian Hu
{"title":"A Unified Strategy for the Synthesis of Diverse Bicyclo[2.2.2]octadiene Ligands","authors":"Wen-Tao Chen, Wen-Cai Luo, Jun-Ting Liang, Yu-Tao He, Ya-Jian Hu","doi":"10.1021/acs.joc.5c00115","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00115","url":null,"abstract":"A new approach for the enantioselective synthesis of various bicyclo[2.2.2]octadiene ligands has been developed, which features a chiral oxazaborolidinium-catalyzed asymmetric Diels–Alder reaction to construct the bicyclo[2.2.2]octane framework. The pivotal ketone <b>12</b> served as a common intermediate that was finally transformed into the desired <i>C</i><sub>1</sub>- and <i>C</i><sub>2</sub>-symmetric chiral dienes. This work provides an alternative method to the reported chiral diene synthesis and would be beneficial to exploration of the potentials of this type of versatile ligand in new asymmetric transformations.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"61 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-04-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143849670","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 Functionalized Indolizines through 1,3-Dipolar Cycloaddition of Zwitterionic Ketenimines and Pyridinium Salts 两性离子酮胺与吡啶盐1,3-偶极环加成合成功能化吲哚嗪类化合物
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-04-19 DOI: 10.1021/acs.joc.5c00295
Farhad Golmohammadi, Chiman Osmani, Frank Rominger, Saeed Balalaie
{"title":"Synthesis of Functionalized Indolizines through 1,3-Dipolar Cycloaddition of Zwitterionic Ketenimines and Pyridinium Salts","authors":"Farhad Golmohammadi, Chiman Osmani, Frank Rominger, Saeed Balalaie","doi":"10.1021/acs.joc.5c00295","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00295","url":null,"abstract":"A straightforward and efficient strategy for the synthesis of fully functionalized indolizines has been developed through a transition metal- and oxidant-free [3 + 2] cycloaddition reaction of zwitterionic ketenimines and pyridinium salts. This versatile method proceeds under mild conditions, affording functionalized indolizines in moderate to good yields. This efficient approach involves an intermolecular [3 + 2] cycloaddition, followed by enamine/imine tautomerization and aromatization. Notably, this method demonstrates broad functional group compatibility and allows for facile scalability, making it a valuable tool for the synthesis of indolizine-based frameworks in organic and medicinal chemistry.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"28 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-04-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143849704","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
A Unified Strategy for the Synthesis of Diverse Bicyclo[2.2.2]octadiene Ligands 多种双环[2.2.2]辛二烯配体合成的统一策略
IF 3.3 2区 化学
Journal of Organic Chemistry Pub Date : 2025-04-19 DOI: 10.1021/acs.joc.5c0011510.1021/acs.joc.5c00115
Wen-Tao Chen, Wen-Cai Luo, Jun-Ting Liang, Yu-Tao He* and Ya-Jian Hu*, 
{"title":"A Unified Strategy for the Synthesis of Diverse Bicyclo[2.2.2]octadiene Ligands","authors":"Wen-Tao Chen,&nbsp;Wen-Cai Luo,&nbsp;Jun-Ting Liang,&nbsp;Yu-Tao He* and Ya-Jian Hu*,&nbsp;","doi":"10.1021/acs.joc.5c0011510.1021/acs.joc.5c00115","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00115https://doi.org/10.1021/acs.joc.5c00115","url":null,"abstract":"<p >A new approach for the enantioselective synthesis of various bicyclo[2.2.2]octadiene ligands has been developed, which features a chiral oxazaborolidinium-catalyzed asymmetric Diels–Alder reaction to construct the bicyclo[2.2.2]octane framework. The pivotal ketone <b>12</b> served as a common intermediate that was finally transformed into the desired <i>C</i><sub>1</sub>- and <i>C</i><sub>2</sub>-symmetric chiral dienes. This work provides an alternative method to the reported chiral diene synthesis and would be beneficial to exploration of the potentials of this type of versatile ligand in new asymmetric transformations.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"90 17","pages":"6073–6078 6073–6078"},"PeriodicalIF":3.3,"publicationDate":"2025-04-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143894138","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 Functionalized Indolizines through 1,3-Dipolar Cycloaddition of Zwitterionic Ketenimines and Pyridinium Salts 两性离子酮胺与吡啶盐1,3-偶极环加成合成功能化吲哚嗪类化合物
IF 3.3 2区 化学
Journal of Organic Chemistry Pub Date : 2025-04-19 DOI: 10.1021/acs.joc.5c0029510.1021/acs.joc.5c00295
Farhad Golmohammadi, Chiman Osmani, Frank Rominger and Saeed Balalaie*, 
{"title":"Synthesis of Functionalized Indolizines through 1,3-Dipolar Cycloaddition of Zwitterionic Ketenimines and Pyridinium Salts","authors":"Farhad Golmohammadi,&nbsp;Chiman Osmani,&nbsp;Frank Rominger and Saeed Balalaie*,&nbsp;","doi":"10.1021/acs.joc.5c0029510.1021/acs.joc.5c00295","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00295https://doi.org/10.1021/acs.joc.5c00295","url":null,"abstract":"<p >A straightforward and efficient strategy for the synthesis of fully functionalized indolizines has been developed through a transition metal- and oxidant-free [3 + 2] cycloaddition reaction of zwitterionic ketenimines and pyridinium salts. This versatile method proceeds under mild conditions, affording functionalized indolizines in moderate to good yields. This efficient approach involves an intermolecular [3 + 2] cycloaddition, followed by enamine/imine tautomerization and aromatization. Notably, this method demonstrates broad functional group compatibility and allows for facile scalability, making it a valuable tool for the synthesis of indolizine-based frameworks in organic and medicinal chemistry.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"90 17","pages":"5973–5985 5973–5985"},"PeriodicalIF":3.3,"publicationDate":"2025-04-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143894139","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
Palladium-Catalyzed Ring-Opening Defluorinative Hiyama Cross-Coupling of gem-Difluorocyclopropanes with Arylsilanes 钯催化开环宝石-二氟环丙烷与芳基硅烷的去氟Hiyama交叉偶联
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-04-18 DOI: 10.1021/acs.joc.5c00564
Zhi-Shang Wang, Dong-Guo Hong, Hongfang Li, Teck-Peng Loh, Ming-Zhu Lu
{"title":"Palladium-Catalyzed Ring-Opening Defluorinative Hiyama Cross-Coupling of gem-Difluorocyclopropanes with Arylsilanes","authors":"Zhi-Shang Wang, Dong-Guo Hong, Hongfang Li, Teck-Peng Loh, Ming-Zhu Lu","doi":"10.1021/acs.joc.5c00564","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00564","url":null,"abstract":"We report an efficient palladium-catalyzed ring-opening defluorinative Hiyama cross-coupling of <i>gem</i>-difluorocyclopropanes with structurally diverse (hetero)arylsilanes through C–C bond activation and C–F bond cleavage. This regioselective ring-opening defluorinative Hiyama cross-coupling features a broad substrate scope with excellent functional group compatibility, affording a diverse variety of linear 2-fluoroallylic scaffolds in good yields with high <i>Z</i>-selectivity.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"137 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-04-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143849706","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
Late-Stage Functionalization Strategies of 1,2,3-Triazoles: A Post-Click Approach in Organic Synthesis 1,2,3-三唑的后期功能化策略：有机合成中的后点击方法
IF 3.3 2区 化学
Journal of Organic Chemistry Pub Date : 2025-04-18 DOI: 10.1021/acs.joc.5c0012510.1021/acs.joc.5c00125
Mangal S. Yadav, Vinay K. Pandey, Manoj K. Jaiswal, Sumit K. Singh, Anindra Sharma, Mayank Singh and Vinod K. Tiwari*, 
{"title":"Late-Stage Functionalization Strategies of 1,2,3-Triazoles: A Post-Click Approach in Organic Synthesis","authors":"Mangal S. Yadav,&nbsp;Vinay K. Pandey,&nbsp;Manoj K. Jaiswal,&nbsp;Sumit K. Singh,&nbsp;Anindra Sharma,&nbsp;Mayank Singh and Vinod K. Tiwari*,&nbsp;","doi":"10.1021/acs.joc.5c0012510.1021/acs.joc.5c00125","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00125https://doi.org/10.1021/acs.joc.5c00125","url":null,"abstract":"<p >The 1,2,3-triazole scaffolds are an important class of biologically privileged heterocyclic compounds with several key applications in chemistry, biology, medicine, agriculture, and material science. The “postclick” functionalization of 1,2,3-triazoles may emerge as a promising tactic for the construction of molecular architectures of therapeutics and is considered to be a growing area of investigation. This interest extends beyond the regioselective Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC) method that involves the trapping of Cu(I)-triazole with suitable precursors. In this Perspective, we highlight the growing impact of postclick strategies in organic synthesis required for the late-stage functionalization of 1,2,3-triazoles with a hope that this emerging concept may provide ample opportunities in modern organic synthesis of notable applications in medicinal chemistry, biology, and materials science.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"90 17","pages":"5731–5762 5731–5762"},"PeriodicalIF":3.3,"publicationDate":"2025-04-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143894047","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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