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Crucial Role of Palladium (0/II) Catalyst in the Synthesis of the Multi-Resonance Thermally Activated Delayed Fluorescence Emitters 钯（0/II）催化剂在合成多共振热激活延迟荧光发射体中的关键作用
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-05-30 DOI: 10.1039/d5qo00522a
Ajeet Chandra, Paramasivam Palanisamy, Aradhya Rajput, Jang Hyuk Kwon
{"title":"Crucial Role of Palladium (0/II) Catalyst in the Synthesis of the Multi-Resonance Thermally Activated Delayed Fluorescence Emitters","authors":"Ajeet Chandra, Paramasivam Palanisamy, Aradhya Rajput, Jang Hyuk Kwon","doi":"10.1039/d5qo00522a","DOIUrl":"https://doi.org/10.1039/d5qo00522a","url":null,"abstract":"Boron and nitrogen/oxygen-based multi-resonance thermally activated delayed fluorescence (MR-TADF) emitters represent cutting-edge OLED technology in both academic and industrial research, demonstrating high color purity and power efficiency. However, the advancement of these emitters is somewhat constrained due to limited synthetic methodologies and low yields of the emitters and their respective precursors. Therefore, comprehensive knowledge of synthetic approaches is necessary, particularly concerning the precursors for improved molecular development. Most precursors for the final emitter are synthesized through the formation of C-C/C-X bonds, which involve palladium-based catalysts in addition of adhitives as crucial reagents. In this review, we thoroughly discuss the synthetic approaches utilized to prepare the intermediates with the palladium catalyst in conjunction with various ligands with the most of the recent reports. Additionally, we outline the general criteria for selecting the Pd catalyst and ligand, along with their respective molar equivalents and the corresponding yields.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"43 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-05-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144177136","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
1,2,3-Trifunctionalization of α,α-Disubstituted Vinyl Aldehydes Enabled by Radical 1,2-Migration of Formyl 甲酰基1,2-自由基迁移导致α，α-二取代乙基醛1,2,3-三官能化
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-05-28 DOI: 10.1039/d5qo00461f
Xiong Yang, Jinmin Luo, Ji Li, Yao Yuan, Gangguo Zhu
{"title":"1,2,3-Trifunctionalization of α,α-Disubstituted Vinyl Aldehydes Enabled by Radical 1,2-Migration of Formyl","authors":"Xiong Yang, Jinmin Luo, Ji Li, Yao Yuan, Gangguo Zhu","doi":"10.1039/d5qo00461f","DOIUrl":"https://doi.org/10.1039/d5qo00461f","url":null,"abstract":"As compared to the well-established 1,2-difunctionalizations, the 1,2,3-trifunctionalization of alkenes has been much less developed, due to the formidable challenges in controlling site-, regio- and diastereoselectivity. Enabled by an uncommon radical-mediated 1,2-migration of carbonyls, a highly controllable 1,2,3-trifunctionalization of α,α-disubstituted vinyl aldehydes with benzoyl peroxide (BPO) as an radical initiator is successfully accomplished, providing a number of trifluoromethylated alkynyl aldehydes in moderate to good yields. Given the site-selective cleavage of allylic C-C bonds and concurrent introduction of three synthetically important functional groups, such as a trifluoromethyl motif, a formyl moiety and an alkyne, it will find widespread applications in both synthetic chemistry and pharmaceutical industry.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"26 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-05-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144154293","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
Dynamic supramolecular nanosheet structures formed by aromatic amphiphiles and their functions 芳香族两亲体形成的动态超分子纳米片结构及其功能
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-05-28 DOI: 10.1039/d5qo00561b
Yanqiu Wang, Myongsoo Lee
{"title":"Dynamic supramolecular nanosheet structures formed by aromatic amphiphiles and their functions","authors":"Yanqiu Wang, Myongsoo Lee","doi":"10.1039/d5qo00561b","DOIUrl":"https://doi.org/10.1039/d5qo00561b","url":null,"abstract":"Supramolecular nanostructures based on the self-assembly of aromatic amphiphiles have received considerable attention because these structures based on non-covalent interactions can be dynamic, leading to switchable nanomaterials in response to external stimuli. The self-assembled materials combine the simplicity of small molecules with the versatility of self-assembly, with a wide range of applications proposed in biomedicine, nanotechnology, <em>etc</em>. Among the diverse self-assembled nanostructures, two-dimensional (2D) nanosheet structures are promising objects in the materials science field due to their ultrathin, large surface areas. Much research effort has been devoted to the study of 2D nanosheet structures based on diverse shapes and conformations of the aromatic segments. This review describes recent progress in the development of nanosheet structures through the self-assembly of rationally designed π-conjugated aromatic amphiphile building blocks. Potential applications, such as chiral separation and biological application, are also discussed. Various views on 2D nanosheet structures have been proposed in the literature, and in this respect, we have attempted to provide a systematic account based on our research progress in recent years. We hope that this will provide a useful reference for 2D nanosheet structures formed by the rational design of aromatic amphiphile self-assembly. We also anticipate that this strategy will provide an opportunity for broadening the application potential of 2D nanosheet structures.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"98 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-05-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144154292","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
Azlactone Rings: Uniting Tradition and Innovation in Synthesis 氮唑内酯环：传统与创新的结合
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-05-28 DOI: 10.1039/d5qo00657k
Marcelo H. R. Carvalho, Geovana F. Vargas, João P. R. S. Ribeiro, Pedro P. de Castro, Giovanni Wilson Amarante
{"title":"Azlactone Rings: Uniting Tradition and Innovation in Synthesis","authors":"Marcelo H. R. Carvalho, Geovana F. Vargas, João P. R. S. Ribeiro, Pedro P. de Castro, Giovanni Wilson Amarante","doi":"10.1039/d5qo00657k","DOIUrl":"https://doi.org/10.1039/d5qo00657k","url":null,"abstract":"Azlactones, also known as oxazolones, are a class of heterocyclic compounds with significant relevance in the synthesis of non-natural amino acids and their derivatives. Their reactivity stems from the presence of both pro-nucleophilic and electrophilic sites, making them highly versatile and enabling a diversity of transformations. In recent years, numerous synthetic strategies utilizing azlactones as key substrates have been developed, encompassing photochemical reactions, cycloadditions, conjugate additions, and dynamic kinetic resolutions. Particular emphasis has been placed on transition-metal catalysis and organocatalyzed processes, which offer precise control over stereo- and/or regioselectivity. This review offers a comprehensive perspective on recent advances in azlactone chemistry, highlighting key reaction mechanisms and activation modes through a variety of examples.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"25 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-05-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144154325","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
Cobalt-Catalyzed Enantioselective Radical Hydroamination of Alkenes with N-Fluorobenzenesulfonimides: Theoretical Insight of Enantio-Determining SN2-like Reductive Elimination 钴催化烯烃与n -氟苯磺酰亚胺的对映选择性自由基氢胺化：对映决定sn2样还原消除的理论见解
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-05-28 DOI: 10.1039/d5qo00696a
Yujie Liang, Bo Zhu, Yabin Jiang, Wei Guan
{"title":"Cobalt-Catalyzed Enantioselective Radical Hydroamination of Alkenes with N-Fluorobenzenesulfonimides: Theoretical Insight of Enantio-Determining SN2-like Reductive Elimination","authors":"Yujie Liang, Bo Zhu, Yabin Jiang, Wei Guan","doi":"10.1039/d5qo00696a","DOIUrl":"https://doi.org/10.1039/d5qo00696a","url":null,"abstract":"The cobalt-catalyzed enantioselective radical hydroamination of alkenes with N-fluorobenzenesulfonimides has been systematically investigated using density functional theory (DFT) calculations. The favorable reaction mechanism consists of six key processes: halogen atom transfer (XAT), N-centered radical addition, transmetalation, hydrogen atom transfer (HAT), C-centered radical addition, and SN2-like reductive elimination. The HAT process is the step that determines regioselectivity. The SN2-like reductive elimination serves as both the enantio-determining step and the rate-determining step of the catalytic cycle. Additionally, the origins of regioselectivity and enantioselectivity have been analyzed from the perspectives of distortion and interaction. This theoretical study offers valuable insights into the activity and selectivity of cobalt-catalyzed enantioselective radical hydroamination at both molecular and atomic levels, aiding the development of asymmetric synthesis.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"119 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-05-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144154326","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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 photocatalytic electron-rich acceptor-involved EDA complexes for Markovnikov addition of alkynes with N-sulfonyl-azoles n-磺酰基唑与炔的马尔可夫尼科夫加成反应中富电子受体参与的光催化EDA配合物
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-05-27 DOI: 10.1039/d5qo00544b
Jinhua Liu, Tang Xiao, Weixiong Chen, Zongjing Hu, Yun Zhao, Shunying Liu
{"title":"A photocatalytic electron-rich acceptor-involved EDA complexes for Markovnikov addition of alkynes with N-sulfonyl-azoles","authors":"Jinhua Liu, Tang Xiao, Weixiong Chen, Zongjing Hu, Yun Zhao, Shunying Liu","doi":"10.1039/d5qo00544b","DOIUrl":"https://doi.org/10.1039/d5qo00544b","url":null,"abstract":"As a potent approach, electron donor–acceptor (EDA) photochemistry offers prospects for new radical transformations under mild reaction conditions. Current EDA strategies commonly use electron-rich molecules as electron donors and electron-poor molecules as electron acceptors to promote radical-trapping reactions. Due to the charge effect, electron-rich molecules are difficult to use as electron acceptors, greatly limiting the types and applicability of the reactions. We herein describe a terminal alkyne-involved ternary EDA complex strategy to activate electron-rich azoles serving as electron acceptors for the unprecedented Markovnikov addition of alkynes. The electron-deficient terminal alkynes are used as “electron bridges” to efficiently form ternary EDA complexes with electron-rich donors (sodium sulfinates) and electron-rich acceptors (<em>N</em>-sulfonyl-azoles). Detailed investigations of the reaction mechanism reveal that sulfonyl radicals are rapidly formed through the promotion of a photocatalyst-enhanced single-electron transfer (SET) process in EDA complexes, yielding the desired compounds in up to 88% isolated yield with high (<em>E</em>)-configuration selectivity and high <em>N</em><small><sup>2</sup></small>-regioselectivity. The developed method also has a wide range of substrate scope, providing a simplified and environmentally friendly approach for the rapid preparation of various challenging conjugated α-sulfonyl-β-triazole olefin compounds. This work provides some insight into the development of electron-rich EDA-enabled radical reactions.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"26 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-05-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144145819","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
Access to (E)-δ-Vinyl-Homoallylic Alcohols/Ethers/Pyrazoles by Ring-opening Nucleophilic Substitution of cyclopropyl allylic alcohols 环丙基烯丙醇开环亲核取代制备(E)-δ-乙烯基均烯丙醇/醚/吡唑
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-05-24 DOI: 10.1039/d5qo00678c
Yulu Zhang, Ying Shao, Jiangtao Sun, Shengbiao Tang
{"title":"Access to (E)-δ-Vinyl-Homoallylic Alcohols/Ethers/Pyrazoles by Ring-opening Nucleophilic Substitution of cyclopropyl allylic alcohols","authors":"Yulu Zhang, Ying Shao, Jiangtao Sun, Shengbiao Tang","doi":"10.1039/d5qo00678c","DOIUrl":"https://doi.org/10.1039/d5qo00678c","url":null,"abstract":"A highly efficient Lewis acid-catalyzed ring-opening nucleophilic substitution of cyclopropyl allylic alcohols has been developed. The use of pyrazoles as nucleophiles, under catalysis with Yb(OTf)3, a series of (E)-δ-vinyl-homoallylic pyrazoles were obtained in moderate to good yields. When the use of water or alcohols as nucleophiles, under the catalyst of Ga(OTf)3, the desired (E)-δ-Vinyl-homoallylic alcohols/ethers were achieved. The cyclopropyl allylic alcohols have been successfully employed for the first time in ring-opening nucleophilic substitution reactions. This method features mild condition, good functional group tolerance.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"138 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-05-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144130115","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
Photoinduced β-fragmentation for efficient pyridine alkylation via N-alkoxypyridinium salts 利用n -烷氧基吡啶盐进行有效吡啶烷基化的光诱导β碎裂
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-05-23 DOI: 10.1039/d5qo00400d
Heng Liu, Fangrui Wu, Zhidong Wan, Changhai Yue, Changsheng Wang, Chengkou Liu, Yuguang Li, Zheng Fang, Hong Qin, Zhao Yang
{"title":"Photoinduced β-fragmentation for efficient pyridine alkylation via N-alkoxypyridinium salts","authors":"Heng Liu, Fangrui Wu, Zhidong Wan, Changhai Yue, Changsheng Wang, Chengkou Liu, Yuguang Li, Zheng Fang, Hong Qin, Zhao Yang","doi":"10.1039/d5qo00400d","DOIUrl":"https://doi.org/10.1039/d5qo00400d","url":null,"abstract":"Pyridine is a key structural motif in pharmaceuticals, and its functionalization is of great research value. We present an efficient alkylation method using <em>N</em>-alkoxypyridinium salts as bifunctional reagents. This protocol operates under mild conditions and offers a broad substrate scope, enabling rapid molecular construction <em>via</em> β-fragmentation with low catalyst loading.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"38 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-05-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144122600","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
Chelation-Controlled Stereospecific Ring-Opening Arylation of α-Aminoaryl-Tethered Alkylidenecyclopropanes: Stereoselective Synthesis of Polysubstituted Conjugated Dienes 螯合控制的α-氨基芳基系链烷基环丙烷立体定向开环芳基化：多取代共轭二烯的立体选择性合成
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-05-23 DOI: 10.1039/d5qo00496a
Miao-Miao Ji, Ying Tang, Wen-Mei Luo, Yong-Yu He, Ai-Jun Ma, Jin-Bao Peng
{"title":"Chelation-Controlled Stereospecific Ring-Opening Arylation of α-Aminoaryl-Tethered Alkylidenecyclopropanes: Stereoselective Synthesis of Polysubstituted Conjugated Dienes","authors":"Miao-Miao Ji, Ying Tang, Wen-Mei Luo, Yong-Yu He, Ai-Jun Ma, Jin-Bao Peng","doi":"10.1039/d5qo00496a","DOIUrl":"https://doi.org/10.1039/d5qo00496a","url":null,"abstract":"Conjugated dienes are vital due to their presence in natural products, bioactive molecules and functional materials as well as their wide synthetic applications. Herein, we report a palladium catalyzed stereospecific ring-opening arylation of α-aminoaryl-tethered alkylidenecyclopropanes for the stereoselective synthesis of 1,1,2-trisubstituted conjugated dienes. This method features excellent functional group tolerance (tolerated functional groups include ether, thioether, halogen, aldehyde, cyano, ester, ketone, trifluoromethoxy and alkenyl), a good substrate scope (35 examples), and high regio- and stereoselectivity.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"20 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-05-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144122602","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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 Progress in Selective Functionalization of Diols via Organocatalysis 有机催化二元醇选择性功能化研究进展
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-05-23 DOI: 10.1039/d5qo00645g
Liaba Niaz, Sojeong Bang, Jeonghyo Lee
{"title":"Recent Progress in Selective Functionalization of Diols via Organocatalysis","authors":"Liaba Niaz, Sojeong Bang, Jeonghyo Lee","doi":"10.1039/d5qo00645g","DOIUrl":"https://doi.org/10.1039/d5qo00645g","url":null,"abstract":"Polyols bearing multiple hydroxyl groups present persistent challenges for site-selective functionalization due to their inherent reactivity similarity. As minimal polyol systems, diols offer a practical and conceptually rich platform for developing regioselective catalytic strategies. This review highlights recent progress in organocatalyzed diol functionalization, with a survey of organocatalysts incorporating boron, nitrogen, and phosphorus-based motifs, as well as emerging photoredox methodologies. These systems enable selective transformation under mild conditions, avoiding stoichiometric activation and minimizing reaction complexity. Steric and electronic effects, along with noncovalent interactions, are examined in detail to rationalize the observed selectivity and guide the rational design of catalysts. Collectively, this review offers a conceptual foundation for advancing sustainable, selective methods in diol derivatization.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"157 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-05-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144122601","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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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