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Photocatalytic Esterification-Peroxidation of Alkenes: Divergent Synthesis of Phenylpropanoids with Vicinal Oxygenated Scaffolds. 光催化酯化-烯烃过氧化反应：邻氧支架苯丙烷的发散合成。
IF 3.3 2区 化学
Journal of Organic Chemistry Pub Date : 2026-10-19 DOI: 10.1021/acs.joc.6c02065
Jun Pan, Haogu Zhang, Yujuan Gui, Zhiping Li
{"title":"Photocatalytic Esterification-Peroxidation of Alkenes: Divergent Synthesis of Phenylpropanoids with Vicinal Oxygenated Scaffolds.","authors":"Jun Pan, Haogu Zhang, Yujuan Gui, Zhiping Li","doi":"10.1021/acs.joc.6c02065","DOIUrl":"https://doi.org/10.1021/acs.joc.6c02065","url":null,"abstract":"<p><p>Vicinal oxygenated scaffolds are prevalent in natural products and pharmaceuticals, yet a general method for divergent access to vicinal oxygenated motifs is still a synthetic challenge. We report a visible-light photoredox esterification-peroxidation of alkenes with carboxylic acids and tert-butyl hydroperoxide. Independent conversion of the peroxy and ester groups gives diverse vicinal oxygenated skeletons. This protocol establishes a unified platform for the divergent construction of vicinal oxygenated scaffolds and concise synthesis of phenylpropanoid natural products.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":" ","pages":""},"PeriodicalIF":3.3,"publicationDate":"2026-10-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149206416","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
Photoredox/Iron Dual-Catalyzed Amination of Sulfenamides for the Synthesis of Primary Sulfinamidines 光氧化还原/铁双催化亚胺胺化合成伯胺亚胺
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2026-10-19 DOI: 10.1021/acs.joc.6c01988
Shaowu Zhu,Nan Wang,Shiyu Liang,Zhenghao Xing,You Zi
{"title":"Photoredox/Iron Dual-Catalyzed Amination of Sulfenamides for the Synthesis of Primary Sulfinamidines","authors":"Shaowu Zhu,Nan Wang,Shiyu Liang,Zhenghao Xing,You Zi","doi":"10.1021/acs.joc.6c01988","DOIUrl":"https://doi.org/10.1021/acs.joc.6c01988","url":null,"abstract":"A mild and efficient photoredox/iron dual-catalyzed method for the synthesis of primary sulfinamidines from readily available sulfenamides has been developed. Reactions proceed smoothly and afford various primary sulfinamidines in moderate to excellent yields. It exhibits a range of sulfenamide substrates and good functional group compatibility. Scale-up synthesis and further transformations demonstrate the scalability and synthetic versatility of this protocol.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"12 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2026-10-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149210906","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
Photo-Induced Thiocyanation/Selenothiocyanation/Cyclization of Indole-3-Carboxamides with KSCN and KSeCN under Mild Conditions 温和条件下KSCN和KSeCN光诱导吲哚-3-羧胺硫氰化/硒代硫氰化/环化
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2026-10-19 DOI: 10.1021/acs.joc.6c02062
Yucai Tang,Jiale Liu,Weiming Xia,Na Long,Kairui Zhang,Fangyuan Ou,Weiguo Zheng,Dong-Fang Jiang,Wei-Min He
{"title":"Photo-Induced Thiocyanation/Selenothiocyanation/Cyclization of Indole-3-Carboxamides with KSCN and KSeCN under Mild Conditions","authors":"Yucai Tang,Jiale Liu,Weiming Xia,Na Long,Kairui Zhang,Fangyuan Ou,Weiguo Zheng,Dong-Fang Jiang,Wei-Min He","doi":"10.1021/acs.joc.6c02062","DOIUrl":"https://doi.org/10.1021/acs.joc.6c02062","url":null,"abstract":"A practical and sustainable photo-induced protocol for the thiocyanation/selenothiocyanation/cyclization of indole-3-carboxamides with cost-effective potassium thiocyanate (KSCN) and potassium selenocyanate (KSeCN) has been developed. This transformation is mediated by the nontoxic organic dye Eosin B and proceeds smoothly at room temperature without the need for metals or bases, offering a practical route to a diverse array of thiocyanated and selenothiocyanated γ-carbolinone derivatives in moderate to good yields (41 examples). Notable advantages include compatibility with gram-scale operations and successful execution under sunlight, which further underscore the synthetic utility of this approach for constructing complex molecular scaffolds.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"218 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2026-10-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149210915","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 Synthesis of Antimicrobial (+)-Streptoaminal-9n via Staudinger-aza-Wittig Reaction Staudinger-aza-Wittig反应合成抗菌(+)-Streptoaminal-9n
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2026-10-19 DOI: 10.1021/acs.joc.6c02046
Chaitanya S. Londhe,Pooja Bhattoo,Shivajirao L. Gholap
{"title":"Total Synthesis of Antimicrobial (+)-Streptoaminal-9n via Staudinger-aza-Wittig Reaction","authors":"Chaitanya S. Londhe,Pooja Bhattoo,Shivajirao L. Gholap","doi":"10.1021/acs.joc.6c02046","DOIUrl":"https://doi.org/10.1021/acs.joc.6c02046","url":null,"abstract":"A novel lipidic metabolite, spirohemiaminal, exhibited substantial growth inhibition of several bacteria, including Escherichia coli, Staphylococcus aureus, and Bacillus subtilis. We report herein the successful total synthesis of (+)-streptoaminal-9n, in 13 steps starting from a chiral epoxide synthesized from l-(-)-malic acid. Our synthetic approach to (+)-streptoaminal-9n is based on the utilization of an intramolecular Staudinger-aza-Wittig cyclization reaction for the construction of a cyclic imine core bearing two stereocenters essential for spirohemiaminal formation. Other key reactions include intramolecular oxa-Michael addition, E-selective Wittig olefination, and regioselective opening of an epoxide with an organocuprate.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"33 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2026-10-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149218916","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
Direct Synthesis of Tetrasubstituted Dienoates by the Strain-Induced “Cut-and-Sew” Strategy of Carbon−Carbon Bonds 应变诱导碳-碳键“剪切-缝合”策略直接合成四取代己烯酸酯
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2026-10-19 DOI: 10.1021/acs.joc.6c01553
Dandugula Sneha Latha,Doma Arun,K. V. Jovan Jose,Srinivasarao Yaragorla
{"title":"Direct Synthesis of Tetrasubstituted Dienoates by the Strain-Induced “Cut-and-Sew” Strategy of Carbon−Carbon Bonds","authors":"Dandugula Sneha Latha,Doma Arun,K. V. Jovan Jose,Srinivasarao Yaragorla","doi":"10.1021/acs.joc.6c01553","DOIUrl":"https://doi.org/10.1021/acs.joc.6c01553","url":null,"abstract":"Abstract The selective cleavage and functionalization of C−C bonds represent a powerful frontier in molecular editing and skeletal reconstruction. We report here a Lewis acid-catalyzed strategy for the formal insertion of propargyl alcohols into the C═C bond of benzoxazine-enaminones under ambient conditions. This “cut-and-sew” cascade enables the precise assembly of highly functionalized tetrasubstituted dienoates with excellent regioselectivity. The protocol is characterized by its broad substrate scope, high chemical yields, and the ability to reorganize unstrained carbon frameworks at room temperature, providing a versatile platform for the divergent synthesis of complex polyenes.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"1 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2026-10-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149210335","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 Reductive C-S Coupling for Preparing S-Aryl/alkyl Containing Peptides 还原C-S偶联制备含s -芳基/烷基肽的研究进展
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2026-10-19 DOI: 10.1021/acs.joc.6c02145
Junhong Wang,Qiujin Fan,Chao Wang,Ying Bai,Xinxin Shao
{"title":"Development of Reductive C-S Coupling for Preparing S-Aryl/alkyl Containing Peptides","authors":"Junhong Wang,Qiujin Fan,Chao Wang,Ying Bai,Xinxin Shao","doi":"10.1021/acs.joc.6c02145","DOIUrl":"https://doi.org/10.1021/acs.joc.6c02145","url":null,"abstract":"Herein, we report a robust reductive coupling of cysteine thiosulfonate derivatives with aryl/alkyl halides, enabling chemoselective modification of peptides. Using zinc as the reducing agent, it provides a divergent platform for construction of Csp3/Csp2─S bonds, featuring base-free reaction conditions, operational simplicity, and broad substrate compatibility.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"9 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2026-10-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149210907","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
Rongalite as a C1 Source for the Modular Synthesis of Methylene-Bridged Bis-chromones and 3-Substituted Methylchromones 以熔铝石为C1源模块化合成亚甲基桥联双色酮和3取代甲基色酮
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2026-10-19 DOI: 10.1021/acs.joc.6c01954
Miao Wang,Xiao-Lu Zhang,Hui-Ying Ren,Shan Jiang,Zhiguo Zhang,Bang-Tun Zhao
{"title":"Rongalite as a C1 Source for the Modular Synthesis of Methylene-Bridged Bis-chromones and 3-Substituted Methylchromones","authors":"Miao Wang,Xiao-Lu Zhang,Hui-Ying Ren,Shan Jiang,Zhiguo Zhang,Bang-Tun Zhao","doi":"10.1021/acs.joc.6c01954","DOIUrl":"https://doi.org/10.1021/acs.joc.6c01954","url":null,"abstract":"Abstract Substantial progress has been made in the synthesis of 3-substituted methylchromones; however, a modular and versatile approach that enables rapid diversification from a single C1 source remains elusive. Herein, we report an efficient and modular approach to the synthesis of both methylene-bridged bis-chromones and 3-substituted methylchromones by using rongalite as a C1 source. Notably, this method enables the rapid and modular construction of a series of methylene-bridged bis-chromones, 3-aminomaleimidyl-, 3-azido-, and 3-arylsulfonyl-substituted methylchromones, as well as the further derivatization into methylene-bridged bis-pyrimidines. The reaction features high efficiency, broad substrate scope, and practical utility, including scale-up synthesis and product transformation into heterocyclic skeletons, demonstrating the versatility of rongalite as a C1 building block.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"151 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2026-10-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149210337","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
Photoredox Catalysis by Phosphorus(V)–Corrole: α-Functionalization of Aldehydes in both Batch and Continuous Flow Conditions 磷(V) -共轭α-功能化在间歇和连续流动条件下的光氧化还原催化作用
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2026-10-19 DOI: 10.1021/acs.joc.6c01436
Ashmita Jain,Pooja Chahal,T. J. Dhilip Kumar,Iti Gupta
{"title":"Photoredox Catalysis by Phosphorus(V)–Corrole: α-Functionalization of Aldehydes in both Batch and Continuous Flow Conditions","authors":"Ashmita Jain,Pooja Chahal,T. J. Dhilip Kumar,Iti Gupta","doi":"10.1021/acs.joc.6c01436","DOIUrl":"https://doi.org/10.1021/acs.joc.6c01436","url":null,"abstract":"A2B-type P(V)-corroles were synthesized with push–pull meso-aryl substituents to examine their photocatalytic application for C–C bond formation in both batch and flow conditions. The developed protocol requires only 0.25 mol % catalyst to synthesize β-formyl esters in high yields (up to 90%). Remarkably, the reaction time decreased from 5 h to 20 min after moving from a batch to a flow reactor. The P(V)-corroles exhibited excellent fluorescence quantum yields (43–53%), and their singlet-state lifetime was ∼3 ns, making them ideal photocatalysts to take part in the energy transfer process with the substrates. The photophysical and mechanistic insights revealed that P(V)-corrole interacts with substrates via both energy- and single-electron-transfer (SET) pathways. Computational studies of the reaction mechanism suggested that SET occurs via the singlet state of the phosphorus corrole.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"1 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2026-10-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149218915","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
Exploring the Couplingof Pyridines with Dearomatized4-Alkylpyridines 探索吡啶与脱芳化4-烷基吡啶的偶联
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2026-10-17 DOI: 10.1021/acs.joc.6c00494
Faizan Rasheed,Jiaqi Shi,Arturo Orellana
{"title":"Exploring the Coupling\u0000of Pyridines with Dearomatized\u00004-Alkylpyridines","authors":"Faizan Rasheed,Jiaqi Shi,Arturo Orellana","doi":"10.1021/acs.joc.6c00494","DOIUrl":"https://doi.org/10.1021/acs.joc.6c00494","url":null,"abstract":"Abstract We describe approaches to the synthesis of dipyridylmethane scaffolds that have potential use in medicinal chemistry. The general strategy exploits the latent nucleophilicity of 4-alkylpyridines and the inherent electrophilicity of pyridines to achieve metal-free coupling. Stable dipyridyl methane scaffolds bearing quaternary pyridylic carbons, tertiary pyridylic alcohols, and pyridylic fluorines are reported.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"33 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2026-10-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149210338","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
Alpha-Oxygenation of Ketones Using TEMPO Disproportionation 使用TEMPO歧化的酮的α -氧合
IF 3.3 2区 化学
Journal of Organic Chemistry Pub Date : 2026-10-16 Epub Date: 2026-10-06 DOI: 10.1021/acs.joc.6c01554
Madison A. Chupela, Jeremy M. Williamson, Brett N. Hemric
{"title":"Alpha-Oxygenation of Ketones Using TEMPO Disproportionation","authors":"Madison A. Chupela,&nbsp;Jeremy M. Williamson,&nbsp;Brett N. Hemric","doi":"10.1021/acs.joc.6c01554","DOIUrl":"10.1021/acs.joc.6c01554","url":null,"abstract":"<p>The alpha-oxygenation of ketones via acid-driven TEMPOdisproportionationis reported. This straightforward and robust protocol from simplestarting materials exhibits an excellent substrate scope in termsof scaffold substitutions, selectivity, and functional group tolerance,with substrate limitations elucidated and highlighted. Furthermore,the mechanism was probed by way of UV–visible spectroscopy,deuterium scrambling experiments, kinetic isotope effect, and Hammettanalysis to illustrate the reaction dynamics.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"91 41","pages":"13674–13681"},"PeriodicalIF":3.3,"publicationDate":"2026-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149088566","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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