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Efficient synthesis of trisubstituted allenes via palladium-catalysed deaminative coupling of tertiary propargylamines with arylsiloxanes 通过钯催化三级丙炔胺与芳基硅氧烷的脱氨基偶联高效合成三取代烯烃
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2024-11-22 DOI: 10.1039/d4qo01780c
Mingjie Liao, Ziqi Yi, Qingqing You, Chuang Liu, Huangdi Feng, Junhai Huang
{"title":"Efficient synthesis of trisubstituted allenes via palladium-catalysed deaminative coupling of tertiary propargylamines with arylsiloxanes","authors":"Mingjie Liao, Ziqi Yi, Qingqing You, Chuang Liu, Huangdi Feng, Junhai Huang","doi":"10.1039/d4qo01780c","DOIUrl":"https://doi.org/10.1039/d4qo01780c","url":null,"abstract":"A novel and efficient method for the palladium-catalysed and highly regioselective synthesis of trisubstituted allenes <em>via</em> deaminative coupling of tertiary propargylamines with arylsiloxanes is reported. Both unactivated propargylamines and arylsiloxanes were activated <em>in situ</em> using Et<small><sub>3</sub></small>N·3HF, followed by cross-coupling to facilitate C–C bond formation through C–N bond cleavage. The method demonstrates exceptional functional group compatibility, high yields, and readily accessible coupling partners.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"254 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-11-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142684799","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
Palladium-Catalyzed NHC Ligand-Controlled Regiodivergent Allyl-Fluoroallyl Cross-Couplings 钯催化的 NHC 配体控制的 Regiodivergent 烯丙基-氟烯丙基交叉耦合反应
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2024-11-21 DOI: 10.1039/d4qo01800a
Yangyang Ma, Boxia Xu, Hua Zhang, Zhiping Li
{"title":"Palladium-Catalyzed NHC Ligand-Controlled Regiodivergent Allyl-Fluoroallyl Cross-Couplings","authors":"Yangyang Ma, Boxia Xu, Hua Zhang, Zhiping Li","doi":"10.1039/d4qo01800a","DOIUrl":"https://doi.org/10.1039/d4qo01800a","url":null,"abstract":"The palladium-catalyzed cross-coupling of (E)-2-fluoroallyl carbonates and allylboronates is reported. The regioselectivity is susceptive to the steric requirements of the NHC ligand, with small IMes favoring the linear fluorinated 1,5-dienes, while the IPrBIDEA featuring sterically-congested character benefits the branched products. Control experiments revealed that either 2-fluoroallyl carbonates or gem-F2CPs could undergo allylation with excellent regioselectivity, yet the former behaved with some lower branched reactivity.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"253 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-11-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142679104","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
Copper-Catalyzed N-H Bond Chalcogenation of Anilines 铜催化苯胺的 N-H 键钙化反应
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2024-11-21 DOI: 10.1039/d4qo01962h
Monak Patel, Rishukumar Panday, Bharatkumar Z. Dholakiya, Togati Naveen
{"title":"Copper-Catalyzed N-H Bond Chalcogenation of Anilines","authors":"Monak Patel, Rishukumar Panday, Bharatkumar Z. Dholakiya, Togati Naveen","doi":"10.1039/d4qo01962h","DOIUrl":"https://doi.org/10.1039/d4qo01962h","url":null,"abstract":"The chalcogen-nitrogen bond (X–N, where X = S, Se) is a key chemical motif in many structures, including inorganic and organic materials, catalysts, protein mimics, and pharmaceuticals. Consequently, developing mild and general methods for constructing N-S and N-Se bonds is important in organic synthesis. Herein, we have developed a novel copper-catalyzed approach to form N-S/N-Se bonds by coupling amines with 1,2 diphenyl disulfide or diphenyl diselenide. This method utilizes readily available substrates to provide the desired products in moderate to good yields. Moreover, the practicality of the reaction is demonstrated through its successful application on a gram scale. The configuration of the product was confirmed through single-crystal X-ray diffraction analysis. Hitherto, no prior reports have been found in the literature for forming N-Se bonds making this reaction an important breakthrough in synthetic organic chemistry.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"66 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-11-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142678811","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
Water-enabled α-C(sp3)–H amination via [1,6]-hydride transfer: green access to diazepino[6,5,4-cd]indoles 通过[1,6]酸酐转移实现水驱动的α-C(sp3)-H胺化：二氮杂卓[6,5,4-cd]吲哚的绿色获取途径
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2024-11-21 DOI: 10.1039/d4qo01761g
Yao-Bin Shen, Xiao-Lin Wang, Qian-Hao Zhuang, Xiao-De An, Bin Qiu, Houchen Wang, Tiesheng Shi, Jian Xiao
{"title":"Water-enabled α-C(sp3)–H amination via [1,6]-hydride transfer: green access to diazepino[6,5,4-cd]indoles","authors":"Yao-Bin Shen, Xiao-Lin Wang, Qian-Hao Zhuang, Xiao-De An, Bin Qiu, Houchen Wang, Tiesheng Shi, Jian Xiao","doi":"10.1039/d4qo01761g","DOIUrl":"https://doi.org/10.1039/d4qo01761g","url":null,"abstract":"Water is an ideal green reaction medium in organic synthesis, and the development of water-enabled transformations to synthesize high value-added molecules is particularly attractive but challenging. Herein, we disclosed the water-enabled <em>α</em>-C(sp<small><sup>3</sup></small>)–H amination of 4-dialkylamino-indole-3-carbaldehydes with primary amines for one-step green synthesis of diazepino[6,5,4-<em>cd</em>]indole derivatives. This reaction proceeded <em>via</em> a cascade aldimine condensation/[1,6]-hydride transfer/cyclization sequence, which featured redox-neutral conditions, water as the green reaction medium, simple operation, high atom- and step-economy, and excellent functional group tolerance.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"81 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-11-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142679103","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
Synthesis, crystal growth, structure and photophysical properties of decafluoroanthracene and its co-crystals with polycyclic arenes 十氟蒽及其与多环烯共晶体的合成、晶体生长、结构和光物理特性
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2024-11-21 DOI: 10.1039/d4qo01825g
Alexandra Friedrich, Lisa Schraut-May, Florian Rauch, Pablo Durand, Johannes Krebs, Paul Niklas Niklas Ruth, Sebastian Hammer, Rüdiger Bertermann, Maik Finze, Stewart Clark, Jens Pflaum, Nicolas Leclerc, Todd B Marder
{"title":"Synthesis, crystal growth, structure and photophysical properties of decafluoroanthracene and its co-crystals with polycyclic arenes","authors":"Alexandra Friedrich, Lisa Schraut-May, Florian Rauch, Pablo Durand, Johannes Krebs, Paul Niklas Niklas Ruth, Sebastian Hammer, Rüdiger Bertermann, Maik Finze, Stewart Clark, Jens Pflaum, Nicolas Leclerc, Todd B Marder","doi":"10.1039/d4qo01825g","DOIUrl":"https://doi.org/10.1039/d4qo01825g","url":null,"abstract":"A series of 1:1 co-crystals of decafluoroanthracene with naphthalene, anthracene, tetracene, pyrene, perylene and triphenylene were grown and characterised using single-crystal X-ray diffraction at low and ambient temperature, (polarisation-dependent) fluorescence spectroscopy, and quantum mechanical computations. All of the molecular co-crystal structures are built from infinite stacks of alternating arene and decafluoroanthracene molecules representing the arene-perfluoroarene supramolecular synthon. Intermolecular interactions and packing features are discussed in detail. As a by-product, the heterodimer of tetracene and decafluoroanthracene was obtained after UV-light irradiation of a solution of the monomers, and structurally characterised. The fluorescence properties of the co-crystals of decafluoroanthracene with naphthalene, tetracene, pyrene, perylene and triphenylene are similar to those of one of their components with only a small bathochromic or hypsochromic shift. This shows that the interaction between the components is weak and fits well into the picture of an arene-perfluoroarene interaction. An exception is 1:1 anthracene:decafluoroanthracene, which shows a bathochromic shift of both excitation and especially emission spectra of the co-crystal compared to those of its components, which indicates weak charge transfer coupling already in the ground state followed by an exciplex-like emission.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"110 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-11-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142679102","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 Ullmann-type cross-coupling reactions: mechanistic insights and emerging challenges 光诱导的乌尔曼型交叉偶联反应：机理认识与新挑战
IF 4.6 1区 化学
Organic Chemistry Frontiers Pub Date : 2024-11-20 DOI: 10.1039/D4QO01814A
Ahmed Th. Abdulghaffar, Haolong Zhang, Qiankun Zhang, Qian Tong, Ruirui Tian, Hao Xu, Jiawei Yang and Yuanqing Xu
{"title":"Photoinduced Ullmann-type cross-coupling reactions: mechanistic insights and emerging challenges","authors":"Ahmed Th. Abdulghaffar, Haolong Zhang, Qiankun Zhang, Qian Tong, Ruirui Tian, Hao Xu, Jiawei Yang and Yuanqing Xu","doi":"10.1039/D4QO01814A","DOIUrl":"10.1039/D4QO01814A","url":null,"abstract":"<p >Photoinduced Ullmann-type cross-coupling reactions have emerged as a significant advancement in organic synthesis, providing an efficient means to form C–C and C–heteroatom bonds under milder, light-driven conditions. Utilizing copper catalysis, these reactions present considerable benefits over traditional thermal methods by improving reaction efficiency and promoting more sustainable processes. This review evaluates recent mechanistic developments, focusing on the nonchain single-electron transfer (SET) mechanism, which is central to the success of these transformations. The discussion includes an up-to-date overview of both homogeneous and heterogeneous catalytic systems, addressing their practical applications and inherent limitations. In addition, this review identifies key challenges, such as catalyst stability, scalability, and the difficulty of activating less reactive substrates like aryl chlorides. To address these limitations, we propose future research directions aimed at overcoming these obstacles.</p>","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":" 1","pages":" 346-367"},"PeriodicalIF":4.6,"publicationDate":"2024-11-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142673379","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
Iridium-Catalyzed Asymmetric Allenylic Substitution of Tertiary Racemic Allenylic Alcohols with Indoles 铱催化的三级外消旋烯丙醇与吲哚的不对称烯丙基取代反应
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2024-11-20 DOI: 10.1039/d4qo01671h
Takahiro Sawano, Manami Kobayashi, Momoko Ishikawa, Eri Ishikawa, Ryo Takeuchi
{"title":"Iridium-Catalyzed Asymmetric Allenylic Substitution of Tertiary Racemic Allenylic Alcohols with Indoles","authors":"Takahiro Sawano, Manami Kobayashi, Momoko Ishikawa, Eri Ishikawa, Ryo Takeuchi","doi":"10.1039/d4qo01671h","DOIUrl":"https://doi.org/10.1039/d4qo01671h","url":null,"abstract":"We report an allenylic substitution of racemic tertiary allenylic alcohols with indoles by a cooperative catalyst consisting of iridium/(P, olefin)-ligand catalyst and Lewis acid to give allenylated indoles bearing a quaternary carbon center with good enantioselectivities. 7-Azaindoles also reacted with allenylic alcohols to form the corresponding allenylated products with high enantioselectivities.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"112 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-11-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142673378","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
(BO)2-doped tetrathia[7]helicenes: synthesis and properties-change induced by “BO bonds inversion” 掺杂(BO)2的四硫杂[7]螺旋烯："BO键反转 "引起的合成与性质变化
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2024-11-20 DOI: 10.1039/d4qo01897d
Luigi Menduti, Clara CB Baldoli, Michael Bolte, Simone Manetto, Claudio Villani, Marta Penconi, Sara Grecchi, Serena ARNABOLDI, Giuseppe Mazzeo, Giovanna Longhi, Alexander Virovets, Hans-Wolfram Lerner, Matthias Wagner, Emanuela Licandro
{"title":"(BO)2-doped tetrathia[7]helicenes: synthesis and properties-change induced by “BO bonds inversion”","authors":"Luigi Menduti, Clara CB Baldoli, Michael Bolte, Simone Manetto, Claudio Villani, Marta Penconi, Sara Grecchi, Serena ARNABOLDI, Giuseppe Mazzeo, Giovanna Longhi, Alexander Virovets, Hans-Wolfram Lerner, Matthias Wagner, Emanuela Licandro","doi":"10.1039/d4qo01897d","DOIUrl":"https://doi.org/10.1039/d4qo01897d","url":null,"abstract":"Helical distortion of polyaromatic hydrocarbons gives rise to a special class of π-conjugated systems, namely helicenes. Owing to their configurational stability and easily tunable optoelectronic properties (via heteroatom-doping), helicenes have recently come to the fore as building blocks for applications in material science (CP-OLEDs, chiroptical switches); in this context, boron-doped helicenes are particularly promising. Herein, we report the synthesis of the new (BO)2-doped tetrathia[7]helicene 2, derived by the formal inversion of (Mes)B‒O moieties in the (previously reported) isomer 1. Theoretical characterization of 2,and comparison with 1,revealed that the inversion of the BO vectors promotes the extension of the LUMO via the central thiophene-benzene-thiophene fragment (and not via the terminal thiophene rings, as in 1), resulting in a considerable lowering of the LUMO energy (ELUMO(2) = – 2.22 eV vs. ELUMO(1) = – 1.65 eV). Spectroscopic studies revealed that the “BO bonds inversion” also contributes to the narrowing of the energy gap (Egopt (2) = 2.90 eV vs.Egopt(1) = 3.16 eV) and causes a significant red-shift of the absorption/emission bands (≈40 nm). Interestingly, besides low fluorescence quantum yield (ΦPL(2) = 7%), 2 showsdetectable Circularly Polarized Luminescence (glum = 0.8×10‒3) and pronounced phosphorescence at low temperature (77 K). (P)-/(M)- enantiomers of 2 were succesfully separated by CSP-UHPLC and proved to be stable (ΔGenant≠= 29.4± 0.1 kcal/mol at 353 K). Racemization studies combined with theoretical calculations, confirmed that BO-doping is an extremely perturbative tool for tuning the mechanical rigidity of tetrathia[7]helicenes(ΔGenant≠(2) is 10 kcal/mol lower than ΔGenant≠(7TH)).","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"18 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-11-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142673376","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
Synthesis and derivatization of an isomer of N-heterotriangulene bearing five-, six- and seven-membered rings around the central nitrogen atom 中心氮原子周围带有五元环、六元环和七元环的 N-heterotriangulene 异构体的合成和衍生化
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2024-11-20 DOI: 10.1039/d4qo02027h
Xinxin Chen, Weifan Wang, Gang Zhang
{"title":"Synthesis and derivatization of an isomer of N-heterotriangulene bearing five-, six- and seven-membered rings around the central nitrogen atom","authors":"Xinxin Chen, Weifan Wang, Gang Zhang","doi":"10.1039/d4qo02027h","DOIUrl":"https://doi.org/10.1039/d4qo02027h","url":null,"abstract":"The functionalization of N-heterotriangulenes has been extensively investigated for their potentials as optoelectronic materials. However, study on the influence of molecular geometry on the property of N-heterotriangulene is still rare. Here we present the synthesis of an isomer of N-heterotriangulene containing five-, six- and seven-membered rings around the central nitrogen atom. The isomer can be further derivatized by condensing with orth-diamine compounds to extend the molecular conjugation. The photophysical and electrochemical properties of related compounds are characterized. The isomer bearing three carbonyl groups demonstrates room temperature phosporescence, which is absent in the corresponding carbonyl-bridged N-heterotriangulene. Furthermore, the chemical oxidation of one of the isomers of N-heterotriangulene to generate cationic radical is also studied.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"14 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-11-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142673381","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
Brønsted Acid-Catalyzed Solvent-Controlled Regioselective Thiolation of 2-Furylcarbinols 布氏酸催化的溶剂控制型 2-呋喃基甲醇区域选择性硫代反应
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2024-11-20 DOI: 10.1039/d4qo01904k
Chunyu Zhang, Tianyu Lin, Qing Liu, Rui Hu, Weidong Rao
{"title":"Brønsted Acid-Catalyzed Solvent-Controlled Regioselective Thiolation of 2-Furylcarbinols","authors":"Chunyu Zhang, Tianyu Lin, Qing Liu, Rui Hu, Weidong Rao","doi":"10.1039/d4qo01904k","DOIUrl":"https://doi.org/10.1039/d4qo01904k","url":null,"abstract":"A novel p-toluenesulfonic acid-catalyzed solvent-controlled regioselective thiolation of 2-furylcarbinols for the efficient and chemoselective preparation of densely functionalized furan- and lactone-based sulfides under mild metal-free conditions has been developed. By using thiols as nucleophiles in DCE at 80 °C, a new reactivity involving a cascade C5-selective nucleophilic substitution/protonation-hydration/C-S bond cleavage/thia-Michael addition leads to lactone-based sulfides rather than the known Piancatelli-type rearrangement products was revealed for the first time. This tunable thiolation protocol enables ready access to both furan- and lactone-based sulfide derivatives with excellent yields by the judicious choice of the reaction solvent.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"3 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-11-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142673380","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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