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Nickel-catalyzed reductive cross-coupling of aziridines and benzyl chlorides. 镍催化叠氮吡啶与苄基氯的还原交偶联。
IF 2.7 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-09-12 DOI: 10.1039/d5ob01299f
Jie Wan, Sen-Lin Wang, Cheng-Ke Liu, Yu-Lu Chen, Hai-Liang Ni, Peng Cao, Ping Hu, Bi-Qin Wang, Bin Chen
{"title":"Nickel-catalyzed reductive cross-coupling of aziridines and benzyl chlorides.","authors":"Jie Wan, Sen-Lin Wang, Cheng-Ke Liu, Yu-Lu Chen, Hai-Liang Ni, Peng Cao, Ping Hu, Bi-Qin Wang, Bin Chen","doi":"10.1039/d5ob01299f","DOIUrl":"https://doi.org/10.1039/d5ob01299f","url":null,"abstract":"<p><p>A nickel-catalyzed reductive cross-coupling of aziridines and benzyl chlorides was realized by using manganese metal as the reducing agent. This protocol afforded a convenient approach for obtaining β-benzyl-substituted arylethylamines bearing various functional groups. The utility of this reaction was also demonstrated by their straightforward conversion to privileged tetrahydroisoquinoline derivatives.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.7,"publicationDate":"2025-09-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145038627","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
Recent advances in photoinduced amidyl radical-mediated remote C(sp3)-H activation via 1,5-hydrogen atom transfer. 光诱导氨基自由基介导的1,5-氢原子转移远端C(sp3)-H活化研究进展。
IF 2.7 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-09-12 DOI: 10.1039/d5ob01197c
Min Liao, Yuanyuan Li, Meiling Ye, Chunjuan Liu
{"title":"Recent advances in photoinduced amidyl radical-mediated remote C(sp<sup>3</sup>)-H activation <i>via</i> 1,5-hydrogen atom transfer.","authors":"Min Liao, Yuanyuan Li, Meiling Ye, Chunjuan Liu","doi":"10.1039/d5ob01197c","DOIUrl":"https://doi.org/10.1039/d5ob01197c","url":null,"abstract":"<p><p>C-H bonds are widely present in organic molecules and play a crucial role in chemical diversification. Among them, the functionalization of unactivated C(sp<sup>3</sup>)-H bonds is highly challenging. The 1,5-hydrogen atom transfer (1,5-HAT) strategy offers an avenue for the functionalization of remote inert C-H bonds with excellent regioselectivity and chemoselectivity. This review looks back at the history and mechanism of the Hofmann-Löffler-Freytag (HLF) reaction and highlights the recent advances in the functionalization of remote inert C(sp<sup>3</sup>)-H bonds triggered by nitrogen-centered radicals (NCRs) <i>via</i> photoinduced 1,5-hydrogen atom transfer processes.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.7,"publicationDate":"2025-09-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145038685","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
DMSO (dimethyl sulfoxide) as a two-methyl source: C-H (trideutero)methylation of (iso)quinolines and their N-oxides. 二甲基亚砜作为二甲基源：异喹啉及其n -氧化物的C-H（三氘）甲基化。
IF 2.7 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-09-12 DOI: 10.1039/d5ob01252j
Palani Natarajan, Pooja, Partigya, Priya, Meena
{"title":"DMSO (dimethyl sulfoxide) as a two-methyl source: C-H (trideutero)methylation of (iso)quinolines and their <i>N</i>-oxides.","authors":"Palani Natarajan, Pooja, Partigya, Priya, Meena","doi":"10.1039/d5ob01252j","DOIUrl":"https://doi.org/10.1039/d5ob01252j","url":null,"abstract":"<p><p>(Trideutero)methylation is an important process in both chemistry and biology. In this context, DMSO(-d<sub>6</sub>) has largely been used as a source of ˙CH<sub>3</sub>/˙CD<sub>3</sub>. Typically, all known DMSO(-d<sub>6</sub>)-based (trideutero)methylation procedures: (i) employ a significant excess of DMSO(-d<sub>6</sub>) as a reagent and solvent and (ii) cleave and utilize only one of the two (trideutero)methyl groups of DMSO(-d<sub>6</sub>). For the first time, using persulfate (S<sub>2</sub>O<sub>8</sub><sup>2-</sup>) and graphitic carbon nitride (g-C<sub>3</sub>N<sub>4</sub>) as the visible-light photocatalyst, we herein describe a methodology that works with merely stoichiometric quantities of DMSO(-d<sub>6</sub>) and cleaves and utilizes both of the (trideutero)methyl groups of DMSO(-d<sub>6</sub>) for the C-H (trideutero)methylation of (iso)quinolines and their <i>N</i>-oxides. We also describe the reusability of the g-C<sub>3</sub>N<sub>4</sub> catalyst and a plausible reaction mechanism. The use of DMSO-d<sub>6</sub> requires careful financial management due to its fairly high retail price (around 600 USD for 100 mL). We thus feel that the (trideutero)methylation method described here, which uses merely stoichiometric amounts of DMSO(-d<sub>6</sub>), is far less expensive and environmentally benign than the methods described in the literature.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.7,"publicationDate":"2025-09-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145038656","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
A facile route to access N-heterocycles using a choline chloride-ethylene glycol-based DES in a dual role. 利用双作用的氯化胆碱-乙二醇基DES获得n -杂环的简便途径。
IF 2.7 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-09-12 DOI: 10.1039/d5ob01090j
Susmita Mandal, Archana Jain, Tarun K Panda
{"title":"A facile route to access N-heterocycles using a choline chloride-ethylene glycol-based DES in a dual role.","authors":"Susmita Mandal, Archana Jain, Tarun K Panda","doi":"10.1039/d5ob01090j","DOIUrl":"https://doi.org/10.1039/d5ob01090j","url":null,"abstract":"<p><p>A green, metal-free, efficient, and simple methodology has been described for the synthesis of a series of biologically and pharmaceutically important nitrogen heterocycles. A variety of 1,3-benzazole compounds are obtained in good to excellent yields by the one-pot reaction between 2-amino/hydroxy/mercaptoanilines with benzylamines under solvent-free conditions using a choline chloride (ChCl)-ethylene glycol (EG) (1 : 2) DES. The inexpensive, biodegradable ChCl-EG (1 : 2) DES plays the dual role of a solvent and catalyst. The DES is recyclable and can be used several times without any significant loss of its activity.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.7,"publicationDate":"2025-09-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145038630","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-driven domino reactions toward nitrogen-containing heterocycles. 含氮杂环的可见光驱动多米诺骨牌反应。
IF 2.7 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-09-12 DOI: 10.1039/d5ob01274k
Yang Li, Dong Xia, Wen-Chao Yang
{"title":"Visible-light-driven domino reactions toward nitrogen-containing heterocycles.","authors":"Yang Li, Dong Xia, Wen-Chao Yang","doi":"10.1039/d5ob01274k","DOIUrl":"https://doi.org/10.1039/d5ob01274k","url":null,"abstract":"<p><p>Nitrogen-containing heterocycles are crucial structural motifs in pharmaceuticals, natural products, and functional materials, with broad applications in medicinal chemistry. The emergence of visible-light photocatalysis has revolutionized their synthesis, offering an environmentally benign approach that operates under mild reaction conditions. Specifically, visible-light-induced domino reactions facilitate multi-step tandem transformations <i>via</i> mechanisms such as single-electron transfer (SET), energy transfer (EnT), or hydrogen atom transfer (HAT), minimizing intermediate isolation and purification steps. This review highlights recent advances in visible-light-induced domino reactions for the synthesis of nitrogen-containing heterocycles. It focuses on key strategies, including nitrogen-centered radical-mediated C-N bond formation and carbon-centered radical-initiated cyclization, discussing their mechanisms, current limitations, and future prospects to provide insights for advancing green synthesis and pharmaceutical science.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.7,"publicationDate":"2025-09-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145038712","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
Catalytic asymmetric kinetic resolution of 2-ethynylaziridines via nucleophilic ring opening with amines. 亲核开环与胺催化2-乙基苄基嘧啶的不对称动力学分解。
IF 2.7 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-09-11 DOI: 10.1039/d5ob01270h
Wen-Tao Ji, Ting-Ting Cheng, Yao Li, Zhuo Chai
{"title":"Catalytic asymmetric kinetic resolution of 2-ethynylaziridines <i>via</i> nucleophilic ring opening with amines.","authors":"Wen-Tao Ji, Ting-Ting Cheng, Yao Li, Zhuo Chai","doi":"10.1039/d5ob01270h","DOIUrl":"https://doi.org/10.1039/d5ob01270h","url":null,"abstract":"<p><p>The enantioselective kinetic resolution of racemic 2-ethynylaziridines <i>via</i> ring opening with amines is realized under the catalysis of a chiral Cu(I)-bisphosphine combination. This protocol provides an expedient way to access synthetically valuable enantioenriched propargylic vicinal diamines (70%-95% yields, 14%-95% ee) and 2-ethynylaziridines (70%-95% recovery rates, 14%-95% ee) within 15-240 h under mild reaction conditions.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.7,"publicationDate":"2025-09-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145032570","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
Oxidative functionalization of cyclopentane-1,3-diones: cell imaging studies of diphenothiazine derivatives. 环戊烷-1,3-二酮的氧化功能化：二吩噻嗪衍生物的细胞成像研究。
IF 2.7 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-09-11 DOI: 10.1039/d5ob01082a
Sapana Dubey, Pragya Trivedi, Madan Sau, Sukanya Mandal, Shreya Roy, Subhrakanta Rout, Subhojit Das, Gokarneswar Sahoo, Damien Bonne, Tapas Das
{"title":"Oxidative functionalization of cyclopentane-1,3-diones: cell imaging studies of diphenothiazine derivatives.","authors":"Sapana Dubey, Pragya Trivedi, Madan Sau, Sukanya Mandal, Shreya Roy, Subhrakanta Rout, Subhojit Das, Gokarneswar Sahoo, Damien Bonne, Tapas Das","doi":"10.1039/d5ob01082a","DOIUrl":"https://doi.org/10.1039/d5ob01082a","url":null,"abstract":"<p><p>This article presents a metal-free expedient approach for simultaneous incorporation of heteroatoms and unsaturation in cyclopentane-1,3-diones <i>via</i> aerial oxidation. We have introduced three distinct methodologies <i>viz.</i> secondary and tertiary amination, dimethylation and diphenothiazine construction (C(sp<sup>2</sup>)-S bonds) to achieve moderate to high yields. This method is highly scalable and compatible with a wide range of substrates. The photophysical properties of the synthesized fluorescent diphenothiazine derivatives were studied and they were found to exhibit impressive fluorescence. Notably, these compounds are non-cytotoxic and promising candidates for cell imaging studies on breast cancer (MCF-7) cell lines.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.7,"publicationDate":"2025-09-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145032533","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
From BN-Dewar benzene to BN-benzvalene: a computational exploration of photoisomerization mechanisms. 从bn -杜瓦苯到bn -苯苯：光异构化机制的计算探索。
IF 2.7 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-09-11 DOI: 10.1039/d5ob01156f
Cristian J Guerra, Yeray A Rodríguez-Núñez, Efraín Polo-Cuadrado, Leandro Ayarde-Henríquez, Diana B Ramírez, Adolfo E Ensuncho
{"title":"From BN-Dewar benzene to BN-benzvalene: a computational exploration of photoisomerization mechanisms.","authors":"Cristian J Guerra, Yeray A Rodríguez-Núñez, Efraín Polo-Cuadrado, Leandro Ayarde-Henríquez, Diana B Ramírez, Adolfo E Ensuncho","doi":"10.1039/d5ob01156f","DOIUrl":"https://doi.org/10.1039/d5ob01156f","url":null,"abstract":"<p><p>This study explores the photochemical conversion of BN-Dewar benzene into BN-benzvalene derivatives, offering a strategic route to heteroatom-containing valence isomers with distinctive electronic properties. Using time-dependent density functional theory (TD-DFT) and electron localization function (ELF) analyses, the excited-state mechanism and associated structural rearrangements were elucidated. Vertical excitation to the S<sub>1</sub> state was found to weaken the CC and B-N bonds while strengthening the N-Si bond in silyl-substituted derivatives, a key factor enabling efficient BN-benzvalene formation. Two minimum energy conical intersections <i>MECI1</i> and <i>MECI2</i> govern the deactivation pathways: <i>MECI1</i> promotes irreversible C2-B bond cleavage and C1-B bond formation, driving the system toward BN-Benzvalene, whereas <i>MECI2</i> enables relaxation back to the BN-Dewar benzene reactant. Nitrogen substitution, particularly with trialkylsilyl groups, significantly enhances the reaction yield by stabilizing charge redistribution and lowering Franck-Condon excitation energies. Nonradiative decay <i>via MECI1</i> proceeds barrierlessly, favoring the production of BN-benzvalene. Finally, ELF analysis reveals that bond formation occurs through electron density migration rather than <i>via</i> radical intermediates.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.7,"publicationDate":"2025-09-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145032535","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-induced regioselective chalcogenation of indoloquinoxalines via cross-dehydrogenative coupling under metal-free, open-air conditions. 在无金属、露天条件下，通过交叉脱氢偶联，可见光诱导吲哚喹啉类化合物的区域选择性加硫。
IF 2.7 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-09-10 DOI: 10.1039/d5ob01088h
Biman Bera, Rahul Dutta, Shubhankar Ghorai, Jhuma Ganguly, Mrinal K Bera
{"title":"Visible-light-induced regioselective chalcogenation of indoloquinoxalines <i>via</i> cross-dehydrogenative coupling under metal-free, open-air conditions.","authors":"Biman Bera, Rahul Dutta, Shubhankar Ghorai, Jhuma Ganguly, Mrinal K Bera","doi":"10.1039/d5ob01088h","DOIUrl":"https://doi.org/10.1039/d5ob01088h","url":null,"abstract":"<p><p>A simple yet efficient method involving a visible-light-induced direct, regioselective chalcogenation of indoloquinoxaline derivatives has been developed. Thiols, disulfides and diselenides were found to be efficient as chalcogenating agents in the presence of Rose Bengal as a photosensitizer. This photoinduced C-H functionalization <i>via</i> a cross-dehydrogenative-coupling (CDC) protocol was carried out at ambient temperature under an open-air atmosphere. A library of chalcogenated indoloquinoxaline derivatives was prepared, and selected compounds were investigated for their photophysical properties. Excellent yield, procedural ease, broad functional group tolerance and exclusive regioselectivity were found to be the noticeable features of this photochemical method, with hassle-free scalability and consistent reproducibility further enhancing its appeal for industrial application.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.7,"publicationDate":"2025-09-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145028616","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
The synthesis of β-enamino esters from the thermal, catalyst-free ring opening of aminocyclopropenones. 氨基环丙烯热无催化剂开环合成β-烯氨基酯。
IF 2.7 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-09-10 DOI: 10.1039/d5ob01290b
Bimod Thapa, Farideh Javid, Cameron Lawson, Mark Soesanto, Karl Hemming
{"title":"The synthesis of β-enamino esters from the thermal, catalyst-free ring opening of aminocyclopropenones.","authors":"Bimod Thapa, Farideh Javid, Cameron Lawson, Mark Soesanto, Karl Hemming","doi":"10.1039/d5ob01290b","DOIUrl":"https://doi.org/10.1039/d5ob01290b","url":null,"abstract":"<p><p>In an attempt to react aminocyclopropenones with cyclic imines in order to synthesise amido-substituted pyrrolizidine natural products, we found that aminocyclopropenones undergo a previously unreported stereospecific and regiospecific catalyst-free, thermal ring-opening reaction with alcohols to yield β-enamino esters (also known as vinylogous carbamates or aminoacrylates). We report 21 examples in 45 to 97% isolated yield. The reaction occurs <i>via</i> nucleophilic attack at the cyclopropenone carbonyl followed by regiospecific ring opening of the cyclopropenone with retention of alkene geometry. Preliminary studies with colon cancer cell line HCT116 show that a sub-set of these β-enamino esters have promising activity.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.7,"publicationDate":"2025-09-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145028648","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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