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Diastereoselective synthesis and structure elucidation of novel ferrocenyl phosphonamidates. 新型二茂铁酰膦酸酯的非对映选择性合成及结构解析。
IF 2.8 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2026-10-16 DOI: 10.1039/d6ob01192f
Annette Benson, Laura Cunningham, Patrick J Guiry
{"title":"Diastereoselective synthesis and structure elucidation of novel ferrocenyl phosphonamidates.","authors":"Annette Benson, Laura Cunningham, Patrick J Guiry","doi":"10.1039/d6ob01192f","DOIUrl":"https://doi.org/10.1039/d6ob01192f","url":null,"abstract":"<p><p>The unexpected formation of ferrocene-containing phosphonamidates was discovered. Under optimised conditions, an array of secondary amines successfully afforded the corresponding analogues, with the major diastereomer being isolated in moderate to good yields (20-35%). The structures of six analogues, as well as the minor intermediate phosphonochloridate, were confirmed by X-ray crystallography.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.8,"publicationDate":"2026-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149190259","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Switchable divergent difunctionalization of terminal alkynes with sodium sulfinates via visible light photocatalysis. 末端炔与亚硫酸钠在可见光催化下的可切换发散双官能化。
IF 2.8 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2026-10-15 DOI: 10.1039/d6ob01356b
Xuming Jiang, Kangfu Chen, Yanping Huo, Yang Gao, Xianwei Li, Qian Chen
{"title":"Switchable divergent difunctionalization of terminal alkynes with sodium sulfinates <i>via</i> visible light photocatalysis.","authors":"Xuming Jiang, Kangfu Chen, Yanping Huo, Yang Gao, Xianwei Li, Qian Chen","doi":"10.1039/d6ob01356b","DOIUrl":"https://doi.org/10.1039/d6ob01356b","url":null,"abstract":"<p><p>Herein, we present a visible light-driven switchable protocol for the divergent difunctionalization of terminal alkynes with sodium sulfinates, wherein the chemoselectivity is governed solely by the presence of an acid additive. Acid-free conditions enable disulfonation to 1,2-disulfonylethenes, whereas acidic conditions favor thiosulfonylation to thiolvinyl sulfones.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.8,"publicationDate":"2026-10-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149190228","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Visible-light-promoted bismuth-catalysed synthesis of dihydroquinoline scaffolds from β-enaminones. 可见光促进铋催化β-胺酮合成二氢喹啉支架。
IF 2.8 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2026-10-15 DOI: 10.1039/d6ob01214k
Lambodar Khadanga, Selvaraj Mohana Roopan
{"title":"Visible-light-promoted bismuth-catalysed synthesis of dihydroquinoline scaffolds from β-enaminones.","authors":"Lambodar Khadanga, Selvaraj Mohana Roopan","doi":"10.1039/d6ob01214k","DOIUrl":"https://doi.org/10.1039/d6ob01214k","url":null,"abstract":"<p><p>Dihydroquinolines are established as important scaffolds in medicinal chemistry owing to their ubiquitous occurrence in bioactive molecules. Utilising water as a solvent in photochemical synthesis provides a synthetic route for chemical transformations under mild conditions. Herein, we report a step-economical and efficient heterogeneous N-doped Bi<sub>2</sub>WO<sub>6</sub> catalysis to obtain a diverse array of dihydroquinolines by using ammonium acetate as a cheap nitrogen source. The protocol exhibits excellent functional group tolerance and is amenable to gram-scale synthesis. The post-synthetic transformations open a window to access structurally complex as well as molecularly diverse heterocyclic scaffolds.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.8,"publicationDate":"2026-10-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149177907","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Unexpected outcome in the reaction of tetrakis(dimethylamino)ethylene (TDAE) with bis(difluoromethyl)disulfide. 四（二甲氨基）乙烯（TDAE）与二（二氟甲基）二硫化物反应的意外结果。
IF 2.8 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2026-10-15 DOI: 10.1039/d6ob01375a
Md Nirshad Alam, Satyajit Majumder, Teruo Umemoto, Lukasz Dobrzycki, William R Dolbier
{"title":"Unexpected outcome in the reaction of tetrakis(dimethylamino)ethylene (TDAE) with bis(difluoromethyl)disulfide.","authors":"Md Nirshad Alam, Satyajit Majumder, Teruo Umemoto, Lukasz Dobrzycki, William R Dolbier","doi":"10.1039/d6ob01375a","DOIUrl":"https://doi.org/10.1039/d6ob01375a","url":null,"abstract":"<p><p>In an attempt to generate a reactive nucleophilic source of the difluoromethylthio group, an unexpected outcome was obtained in the reaction of tetrakis(dimethylamino)ethylene (TDAE) with bis(difluoromethyl)disulfide (HCF<sub>2</sub>SSCF<sub>2</sub>H). Although the TDAE<sup>2+</sup>(HCF<sub>2</sub>S<sup>-</sup>)<sub>2</sub> intermediate appeared to be formed, it proved insufficiently reactive to be alkylated by benzyl bromide and other activated alkyl bromides. Instead, the intermediate lost the fluoride ion to form SCHF, which then proceeded to convert to two unexpected products, which were characterized using spectroscopic tools and X-ray analysis.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.8,"publicationDate":"2026-10-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149190217","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Insights into boric acid-mediated chemoselective transformation of D-glucosamine. 硼酸介导的d-氨基葡萄糖化学选择性转化的研究进展。
IF 2.8 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2026-10-15 DOI: 10.1039/d6ob01298a
Tingting Shen, Shihao Sun, Hui Xi, Xiaoxu Li, Bo Kong, Wei Luo, Donghui Wei, Peng Li
{"title":"Insights into boric acid-mediated chemoselective transformation of D-glucosamine.","authors":"Tingting Shen, Shihao Sun, Hui Xi, Xiaoxu Li, Bo Kong, Wei Luo, Donghui Wei, Peng Li","doi":"10.1039/d6ob01298a","DOIUrl":"https://doi.org/10.1039/d6ob01298a","url":null,"abstract":"<p><p>Boric acid (B(OH)<sub>3</sub>) can significantly improve the chemoselectivity of the transformation of D-glucosamine to 2,5-deoxyfructosazine (2,5-DOF), but the origin of the chemoselective formation of 2,5-DOF over fructosazine (FZ) has long remained unknown. In this work, we systematically investigated the possible mechanisms of boric acid-mediated transformation of D-glucosamine using density functional theory (DFT). The fundamental reaction pathway includes four stages: ring-opening, C-N bond formation, dehydration, and selective generation of 2,5-DOF over FZ. This study shows that boric acid plays a key role in both the dehydration stage and the selective formation stage of 2,5-DOF. Notably, the dehydration stage has been theoretically studied for the first time and identified as the rate-determining step, and the pathway promoted by two molecules of boric acid, 2B(OH)<sub>3</sub>, is more energetically favorable than the widely proposed pathway involving the coordination of only one boric acid. Using the projection of orbital coefficient vector (POCV) method, we further analyzed the atomic activity vector and Fukui function vector values at the possible reaction sites in the presence and absence of boric acid to explore the role of boric acid and predict the chemoselectivity. This work clarifies the specific roles of boric acid and advances the application of theoretical calculations to this kind of organocatalytic reaction with high chemoselectivity.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.8,"publicationDate":"2026-10-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149190252","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Nickel-catalyzed one-pot C-H alkylation of (hetero)arenes enabled by in situ electrophilic iodination and reductive coupling with alkyl pyridinium salts. 原位亲电碘化和烷基吡啶盐还原偶联使镍催化（杂）芳烃的一锅C-H烷基化。
IF 2.8 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2026-10-15 DOI: 10.1039/d6ob01307d
Yongming Zhang, Fan Wu, Feng Ni
{"title":"Nickel-catalyzed one-pot C-H alkylation of (hetero)arenes enabled by <i>in situ</i> electrophilic iodination and reductive coupling with alkyl pyridinium salts.","authors":"Yongming Zhang, Fan Wu, Feng Ni","doi":"10.1039/d6ob01307d","DOIUrl":"https://doi.org/10.1039/d6ob01307d","url":null,"abstract":"<p><p>Herein, we report a practical one-pot protocol for the formal C(sp<sup>2</sup>)-H alkylation of (hetero)arenes by combining <i>in situ</i> I<sub>2</sub>/Selectfluor-mediated electrophilic iodination with nickel-catalysed reductive cross-coupling using readily accessible alkyl pyridinium salts. The transformation exhibits a broad arene scope and tolerates various functional groups and a range of heterocycles. Importantly, late-stage functionalization of complex bioactive molecules, including dapagliflozin, aniracetam, clofibrate and fenofibrate derivatives, is demonstrated. This method utilized two abundant chemical feedstocks for forging C(sp<sup>2</sup>)-C(sp<sup>3</sup>) bonds, offering a versatile and operationally simple entry to alkylarenes.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.8,"publicationDate":"2026-10-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149190270","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
En route towards "organic sodium": strongly excited-state reducing phenothiazines with application in photoredox catalysis. 在通往“有机钠”的道路上：强激发态还原吩噻嗪在光氧化还原催化中的应用。
IF 2.8 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2026-10-14 DOI: 10.1039/d6ob01175f
Carl J Rettig, Julia Steinfort, Tim Gathge, Robert Viehbeck, Philippe de Bary, Lena J Daumann, Thomas J J Müller, Klaus Schaper
{"title":"<i>En route</i> towards \"organic sodium\": strongly excited-state reducing phenothiazines with application in photoredox catalysis.","authors":"Carl J Rettig, Julia Steinfort, Tim Gathge, Robert Viehbeck, Philippe de Bary, Lena J Daumann, Thomas J J Müller, Klaus Schaper","doi":"10.1039/d6ob01175f","DOIUrl":"10.1039/d6ob01175f","url":null,"abstract":"<p><p>The phenothiazine scaffold with a strongly electron-donating substituent is a suitable structural motif for the development of new photoredox catalysts operating in the oxidative quenching cycle. The design, investigation and application of new, highly reducing tri-substituted phenothiazines, which can be readily accessed in a one-pot procedure, reveal sodium-like oxidation potentials upon excitation with UV light.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":"8056-8060"},"PeriodicalIF":2.8,"publicationDate":"2026-10-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148987216","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Ultrasonic-assisted one-pot synthesis of mono- and polycyclic compounds via NIS-promoted selenocyclization of dienes with elemental selenium and thiols. 超声辅助一锅合成单环和多环化合物，通过nis促进二烯与元素硒和硫醇的硒环化。
IF 2.8 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2026-10-14 DOI: 10.1039/d6ob01209d
Evgeny O Kurkutov, Semen Yu Gubal, Elizaveta K Sivushkova, Sergey V Zinchenko, Bagrat A Shainyan
{"title":"Ultrasonic-assisted one-pot synthesis of mono- and polycyclic compounds <i>via</i> NIS-promoted selenocyclization of dienes with elemental selenium and thiols.","authors":"Evgeny O Kurkutov, Semen Yu Gubal, Elizaveta K Sivushkova, Sergey V Zinchenko, Bagrat A Shainyan","doi":"10.1039/d6ob01209d","DOIUrl":"10.1039/d6ob01209d","url":null,"abstract":"<p><p>Herein, an ultrasonic-assisted one-pot protocol of selenosulfenylation for the synthesis of new mono- and polycyclic selenium heterocycles is reported. The reaction of elemental selenium with thiols and different dienes in the presence of various oxidizing agents has been studied. The reaction with non-conjugated dienes, such as 4-vinylcyclohexene, 5-vinyl-2-norbornene, 1,5-cyclooctadiene, and hexa-1,5-diene, activated by <i>N</i>-iodosuccinimide, selectively leads to the products of their cyclization with the selenium atom. The reaction with 5-vinyl-2-norbornene proceeds stereoselectively and results in stable iodosulfenylselenylated and disulfenylselenylated adducts having the previously unknown tricyclic selenium-containing skeleton. The mechanism is proposed and confirmed by theoretical calculations.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":"8139-8147"},"PeriodicalIF":2.8,"publicationDate":"2026-10-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149072861","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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 3-acylated 1-aminoisoquinolin-4-ols via construction of a fully substituted pyridine moiety. 通过构建全取代吡啶片段合成3-酰化1-氨基异喹啉-4-醇。
IF 2.8 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2026-10-14 DOI: 10.1039/d6ob00919k
Nayeon Kim, Sunhee Lee, Ikyon Kim
{"title":"Synthesis of 3-acylated 1-aminoisoquinolin-4-ols <i>via</i> construction of a fully substituted pyridine moiety.","authors":"Nayeon Kim, Sunhee Lee, Ikyon Kim","doi":"10.1039/d6ob00919k","DOIUrl":"10.1039/d6ob00919k","url":null,"abstract":"<p><p>Described herein is an annulative functionalization approach to synthesize the 3-acylated 1-aminoisoquinolin-4-ol skeleton from a base-catalyzed reaction of 2-formylbenzonitrile with α-azidoketone under mild conditions, enabling the facile assembly of a fully functionalized aminopyridinol moiety <i>via</i> a domino procedure involving an aldol reaction, imine formation, tautomerization, and cycloisomerization.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":"8126-8138"},"PeriodicalIF":2.8,"publicationDate":"2026-10-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149072946","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Iodine-mediated desulfurative cyclization to trifunctionalized pyrido[1,2-b]indazoles. 碘介导的三官能化吡啶[1,2-b]吲哚的脱硫环化。
IF 2.8 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2026-10-14 DOI: 10.1039/d6ob01420h
Jun Ma, Si-Yu Song, Li-Sheng Wang, Chun-Yan Wu, Yu-Jia Fan, Zhi-Cheng Yu, An-Xin Wu
{"title":"Iodine-mediated desulfurative cyclization to trifunctionalized pyrido[1,2-<i>b</i>]indazoles.","authors":"Jun Ma, Si-Yu Song, Li-Sheng Wang, Chun-Yan Wu, Yu-Jia Fan, Zhi-Cheng Yu, An-Xin Wu","doi":"10.1039/d6ob01420h","DOIUrl":"https://doi.org/10.1039/d6ob01420h","url":null,"abstract":"<p><p>While thioamides are widely utilized as nucleophilic or ambiphilic synthons to construct heterocycles, strategies harnessing their inherent electrophilic reactivity to form carbon-heteroatom bonds through desulfurization with intact amino groups reserved for downstream cyclization are scarcely documented. Herein, we report a metal-free I<sub>2</sub>-DMSO-mediated tandem cyclization protocol that exploits the underexplored electrophilic nature of thioamides for facile one-pot assembly of trifunctionalized pyrido[1,2-<i>b</i>]indazoles. Moreover, further derivatization of these products furnishes 1-imino-3-phenyl-1<i>H</i>,3<i>H</i>-furo[3',4':4,5]pyrimido[1,2-<i>b</i>]indazol-11-amine, an unprecedented fused polycyclic scaffold.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.8,"publicationDate":"2026-10-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149177882","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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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