Organic chemistry frontiers : an international journal of organic chemistry最新文献_第2页

Copper-catalyzed enantioselective sulfonylation from sulfur dioxide: generation of tertiary propargylic sulfones† 铜催化的二氧化硫对映体选择性磺化反应：生成三级丙炔基砜

Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2025-03-03 DOI: 10.1039/d4qo02389g

Chen Guo , Jiapian Huang , Shengqing Ye , Min Yang , Jie Wu

引用次数: 0

A copper-catalyzed enantioselective cycloaddition/amination cascade of azomethine imines, alkynes and O-benzoylhydroxylamines† 铜催化亚甲基亚胺、炔和邻苯甲酰羟胺的对映选择性环加成/胺化级联反应

Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2025-03-03 DOI: 10.1039/d5qo00061k

Tai-Gang Fan , Bo-Xun Sun , Wei Jiang , Jia Hu , Li-Bo Yang , Yuan Qu , Ya-Min Li

引用次数: 0

Photoinduced reductive cyclization of 2-nitroaryl-tethered carbonyl compounds: an approach for accessing nitrogen-fused heterocycles† 2-硝基拴住羰基化合物的光诱导还原环化：一种获得氮融合杂环的方法

Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2025-03-03 DOI: 10.1039/d5qo00363f

Yulong Du , Yuhui Wu , Jiarui Tang , Jianhui Chen , Yanshu Luo , Yuanzhi Xia

引用次数: 0

A DFT investigation of the mechanism of photoinduced radical borylation of alkyl bromides: elucidation of base-mediated photoinduced SET and SN2 processes† 光诱导烷基溴化物自由基硼化反应机理的DFT研究：碱基介导的光诱导SET和SN2过程的阐释

Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2025-03-03 DOI: 10.1039/d5qo00048c

Nana Ma , Qiongjin Wang , Die Zhao , Bowen Duan , Shujun Li , Guisheng Zhang

{"title":"A DFT investigation of the mechanism of photoinduced radical borylation of alkyl bromides: elucidation of base-mediated photoinduced SET and SN2 processes†","authors":"Nana Ma , Qiongjin Wang , Die Zhao , Bowen Duan , Shujun Li , Guisheng Zhang","doi":"10.1039/d5qo00048c","DOIUrl":"10.1039/d5qo00048c","url":null,"abstract":"<div><div>The transition-metal-free borylation of alkyl halides has received widespread attention due to environmental and economic considerations. In particular, the visible-light-induced radical borylation of alkyl halides catalyzed by 4-phenylpyridine has been achieved, even for unactivated alkyl bromides. In these reactions, the visible-light-induced radical borylation of alkyl bromides has demonstrated the formation of nucleophilic products and proposed a mechanism where the activation of unreactive alkyl bromides occurs through an S<sub>N</sub>2/photoinduced radical formation pathway. However, a systematic investigation of the mechanism of this type of reaction is lacking. Several crucial aspects necessitate further elucidation, including the formation of a super electron donor (SED), the competition between photoinduced single-electron transfer (SET) and S<sub>N</sub>2 processes, and the precise nature of MeO<sup>−</sup>. In this study, we employed density functional theory (DFT) calculations to address these issues. The calculated results indicate that in the 4-PhPy/B<sub>2</sub>cat<sub>2</sub>/MeONa system, the generation of alkyl radicals mainly results from the two successive photoinduced SET processes alongside S<sub>N</sub>2/photoinduced SET. Notably, in addition to the <em>N</em>-boryl pyridyl anion () and the ate complex (), the resulting anionic radical () and radical as SEDs also play crucial roles in generating in the pathways subsequent to the SET of and , respectively. MeO<sup>−</sup> plays a critical role in both the nucleophilic substitution and SET processes through the O<sup><em>δ</em>−</sup>⋯B<sup><em>δ</em>+</sup> Lewis acid–base interaction, facilitated by decreased electron delocalization from sp<sup>2</sup> to sp<sup>3</sup> of the B center, making it easier to donate electrons.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 10","pages":"Pages 3163-3176"},"PeriodicalIF":0.0,"publicationDate":"2025-03-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143734058","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Stereoselective synthesis of allylic sulfones via palladium-catalyzed hydrosulfonylation of cyclopropenes† 钯催化环丙烯氢磺化立体选择性合成烯丙基砜

Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2025-03-03 DOI: 10.1039/d5qo00062a

Suliang Wang , Xuening Li , Jian Song , Xianjie Fang

引用次数: 0

A multi-resonant thermally activated delayed fluorescence emitter with a twisted second-generation carbazole dendron showing suppressed concentration quenching and its use in solution-processed organic light-emitting diodes† 具有第二代扭曲咔唑树突的多共振热激活延迟荧光发射器及其在溶液处理有机发光二极管中的应用

Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2025-03-03 DOI: 10.1039/d5qo00146c

Jingxiang Wang , Yuka Yasuda , Yongxia Ren , Ryo Kondo , David B. Cordes , Hironori Kaji , Eli Zysman-Colman

{"title":"A multi-resonant thermally activated delayed fluorescence emitter with a twisted second-generation carbazole dendron showing suppressed concentration quenching and its use in solution-processed organic light-emitting diodes†","authors":"Jingxiang Wang , Yuka Yasuda , Yongxia Ren , Ryo Kondo , David B. Cordes , Hironori Kaji , Eli Zysman-Colman","doi":"10.1039/d5qo00146c","DOIUrl":"10.1039/d5qo00146c","url":null,"abstract":"<div><div>Multi-resonant thermally activated delayed fluorescence (MR-TADF) emitters have drawn significant interest for use in organic lighting-emitting diodes (OLEDs) as they typically have bright and narrowband emission. However, their rigid, planar structures result in poor solubility in organic solvents and a tendency to aggregate. This usually results in severe aggregation-caused quenching (ACQ), which hinders in particular, their application in solution-processed OLEDs. Herein, a solution-processable MR-TADF emitter has been designed, synthesized and studied. The presence of eight <em>tert</em>-butyl groups and the use of second-generation donor dendrons help enhance its solubility and suppress the ACQ. exhibits narrowband green emission at 493 nm, with a full-width at half maximum of 32 nm and a high photoluminescence quantum yield (<em>Φ</em><sub>PL</sub>) of 93% in toluene. The <em>Φ</em><sub>PL</sub> values in 1–10 wt% doped films in mCP are slightly lower but still reach up to 80%. Solution-processed OLEDs using this emitter showed maximum external quantum efficiencies (EQE<sub>max</sub>) of 11.4 and 10.6% at 5 and 10 wt% doping concentration, respectively. This work demonstrates a strategy to synthesize solution processable MR-TADF emitters for use in solution-processed OLEDs.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 10","pages":"Pages 3279-3287"},"PeriodicalIF":0.0,"publicationDate":"2025-03-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143570337","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Interrupted intramolecular [3 + 2] to 5-endo-dig cyclization: [3 + 2] cycloaddition of nitrile ylides of diazo esters: photo-induced solvent-free gem-diamination to synthesize α-amino-α-substituted α-amino esters† 中断的[3+2]到5-内环化；[3+2]重氮酯的腈酰环加成；光诱导无溶剂宝石二聚成α-氨基-α-取代α-氨基酯

Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2025-03-03 DOI: 10.1039/d4qo02332c

Haya Khan , Yashika Tyagi , Roopam Pandey , Pranoy Menon , Subhabrata Sen

引用次数: 0

Photocatalytic intermolecular [2 + 2] cycloaddition/dearomatization of indoles: easy access to cyclobutane-fused indolines† 光催化吲哚分子间[2+2]环加成/脱芳化：易于获得环丁烷融合吲哚

Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2025-03-03 DOI: 10.1039/d4qo02302a

Zeng Han , Lianhui Wang , Yuanqi Luo , Xiuling Cui

引用次数: 0

Highly efficient low-valence tungsten-catalyzed deoxygenative reduction of tertiary amides to amines with pinacolborane† 高效低价钨催化的叔胺与蒎烯硼烷脱氧还原制胺

Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2025-03-03 DOI: 10.1039/d4qo02340d

Biao Cheng , Jialong Xv , Xiang Ren , Yuanyuan Li , Xiaoming Ji , Zhan Lu

引用次数: 0

Metal-free photoredox catalyzed formation of S–C–S and C–S bonds through coupling of diaryl sulfides/benzyl chlorides with dichloromethyl derivatives† 无金属光氧化还原催化二氯甲基衍生物偶联二芳基硫化物/苄基氯化物形成S-C-S和C-S键

Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2025-03-03 DOI: 10.1039/d5qo00218d

Chun-Hong Long , Hang Cai , Yuan Sun , Zhao-Nan Cai , Hong-Bo Qin

{"title":"Metal-free photoredox catalyzed formation of S–C–S and C–S bonds through coupling of diaryl sulfides/benzyl chlorides with dichloromethyl derivatives†","authors":"Chun-Hong Long , Hang Cai , Yuan Sun , Zhao-Nan Cai , Hong-Bo Qin","doi":"10.1039/d5qo00218d","DOIUrl":"10.1039/d5qo00218d","url":null,"abstract":"<div><div>A metal-free photoredox method for the synthesis of S–C–S and C–S bonds has been developed, offering a sustainable and efficient approach for producing diaryl dithioacetals and aryl benzyl sulfides. This method employs 4CzIPN as a photocatalyst and DIPEA as a base, enabling the formation of sulfur and carbon radicals through single electron transfer (SET) and halogen atom transfer (XAT) mechanisms. This protocol features a broad substrate scope, moderate to excellent yields, and scalability under solvent-free conditions or using water as a green solvent. Gram-scale synthesis and sunlight-driven reactions demonstrate its potential for industrial applications. Mechanistic studies, including fluorescence quenching and radical trapping experiments, have confirmed that DIPEA serves as a quencher of the excited state of 4CzIPN and that the reaction involves a radical pathway. This environmentally friendly strategy provides a versatile platform for constructing valuable sulfur-containing compounds with applications in synthetic chemistry and drug development.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 10","pages":"Pages 3264-3270"},"PeriodicalIF":0.0,"publicationDate":"2025-03-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143589911","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0