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Construction of Oxabicyclo[3.2.1]octanes via Palladium-Catalyzed Intermolecular [3+4] Cycloadditions of Vinylidenecyclopropane-diesters with Pyrroles or Indoles bearing a Trifluoroacetyl Group and the Related Hydroamination Reaction 钯催化的乙烯基环丙烷二酯分子间[3+4]环加成与含三氟乙酰基的吡咯或吲哚的构建氧沙环[3.2.1]辛烷及其氢胺化反应
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-09-24 DOI: 10.1039/d5qo01027f
Bo Zhang, Ze-Ren Yang, Yin Wei, Min Shi
{"title":"Construction of Oxabicyclo[3.2.1]octanes via Palladium-Catalyzed Intermolecular [3+4] Cycloadditions of Vinylidenecyclopropane-diesters with Pyrroles or Indoles bearing a Trifluoroacetyl Group and the Related Hydroamination Reaction","authors":"Bo Zhang, Ze-Ren Yang, Yin Wei, Min Shi","doi":"10.1039/d5qo01027f","DOIUrl":"https://doi.org/10.1039/d5qo01027f","url":null,"abstract":"In this paper, we reported a palladium-catalyzed rapid construction of oxabicyclo[3.2.1]octane skeletons through an intermolecular [3+4] cycloaddition of vinylidenecyclopropane-diesters (VDCP-diesters) with pyrroles and indoles bearing a trifluoroacetyl group at the 2-position under mild conditions. This cycloaddition proceeds through a key zwitterionic π-propargyl palladium species derived from VDCP-diester, affording the corresponding cycloadducts in moderate to good yields and ee values along with good substrate applicability. The strong electron-withdrawing effect of trifluoroacetyl is essential for this [3+4] cycloaddition reaction. Replacing it with other acyl groups triggers the reconstruction of the cyclopropane ring to produce a series of vinylcyclopropane products (VCP products) through a hydroamination reaction pathway. The plausible reaction mechanisms are proposed on the basis of control and deuterium-labeling experiments as well as a Fukui function analysis.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"83 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-09-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145127975","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
Saddle-Shaped Chiral Nanographenes Embedded with Dipleiadiene and Thia[6]helicene Units 鞍形手性纳米石墨烯嵌入双二烯和螺旋烯单元
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-09-23 DOI: 10.1039/d5qo01263e
Fengkun Chen, Yufei Xia, Wang Sun, Qiao Yang, Li Jiang, Ying Wang, Yunbin Hu
{"title":"Saddle-Shaped Chiral Nanographenes Embedded with Dipleiadiene and Thia[6]helicene Units","authors":"Fengkun Chen, Yufei Xia, Wang Sun, Qiao Yang, Li Jiang, Ying Wang, Yunbin Hu","doi":"10.1039/d5qo01263e","DOIUrl":"https://doi.org/10.1039/d5qo01263e","url":null,"abstract":"Negatively curved chiral nanographenes (NGs) have recently garnered significant interest as aesthetically unique carbon allotropes with unique topologies and extraordinary physicochemical properties. However, the construction of such π-systems bearing multiple heptagons and helical chirality remains challenging. Herein, we reported the successful preparation of a saddle-shaped chiral NG 2 incorporating two heptagons and a thia[6]helicene unit, along with a triple thia[6]helicene 4, by controlled Scholl reactions. Single crystal X-ray diffraction analysis revealed that 2 adopted a highly distorted architecture with a pronounced torsional angle of 30.3° with regard to the central benzene ring. The formation of two additional heptagons in 2 resulted in red-shifted absorption and emission, as well as enhanced fluorescence quantum yield compared to 4. The oxidation of the sulfur atoms in compounds 2 and 4 to their corresponding sulfone-incorporated analogues, 3 and 5, respectively, was found to be an efficient approach to modulate their electronic and electrochemical properties. Furthermore, the relatively high racemization barriers of these compounds enabled their chiral resolution and facilitated the characterization of their chiroptical properties.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"51 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-09-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145116517","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
Lewis Acid-Mediated Intermolecular [2π+2σ] Cycloaddition Between Enol Ethers and Bicyclo[1.1.0]butanes 烯醇醚与双环丁烷[1.1.0]分子间[2π+2σ]环加成
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-09-23 DOI: 10.1039/d5qo01194a
Shijie Zhu, Yukun Meng, Zhifei Zhao, Shi-Wu Li
{"title":"Lewis Acid-Mediated Intermolecular [2π+2σ] Cycloaddition Between Enol Ethers and Bicyclo[1.1.0]butanes","authors":"Shijie Zhu, Yukun Meng, Zhifei Zhao, Shi-Wu Li","doi":"10.1039/d5qo01194a","DOIUrl":"https://doi.org/10.1039/d5qo01194a","url":null,"abstract":"A Lewis acid-promoted [2π+2σ] cycloaddition strategy enables the construction of bicyclo[2.1.1]hexanes (BCHs) from enol ethers and bicyclo[1.1.0]butanes (BCBs), with excellent functional group tolerance observed for both reactants. Successful scale-up experiments and further derivatization of BCHs demonstrate the robustness of this methodology for accessing complex carbocyclic frameworks.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"53 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-09-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145127918","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
Sub-Room Temperature Transfer Hydrogenation of α,β-Unsaturated Ketones Using Methanol as a Hydrogen Source 以甲醇为氢源的α，β-不饱和酮的亚室温转移加氢
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-09-23 DOI: 10.1039/d5qo01133g
Sandip Bapu Khatal, Rahul Daga Patil, Manohar Shivaji Padmor, Sanjay Pratihar
{"title":"Sub-Room Temperature Transfer Hydrogenation of α,β-Unsaturated Ketones Using Methanol as a Hydrogen Source","authors":"Sandip Bapu Khatal, Rahul Daga Patil, Manohar Shivaji Padmor, Sanjay Pratihar","doi":"10.1039/d5qo01133g","DOIUrl":"https://doi.org/10.1039/d5qo01133g","url":null,"abstract":"A chemoselective transfer hydrogenation of α,β-unsaturated ketones at sub-room temperature (15–25 °C) using methanol and an Ir(III) pyridylidene–indole catalyst is reported. The protocol offers broad substrate scope, gram-scale synthesis without chromatographic purification, and site-selective deuteration under reduced energy input. Mechanistic investigations, including kinetic, control, and isotope-labelling studies, support a concerted hydrogen transfer pathway facilitated by strong ligand σ-donation, offering a practical low-energy route to defined hydrogenated products.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"40 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-09-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145127977","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
Diversity-Oriented Synthesis of Poly-substituted Benzofuran Derivatives Bearing Amino Groups at 2- or 3-Positions: Rh- or Ni-Catalyzed Cycloisomerization between Ynamides and Enol Ethers 含2位或3位氨基的多取代苯并呋喃衍生物的合成：酰胺和烯醇醚之间的Rh或ni催化环异构化
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-09-22 DOI: 10.1039/d5qo01123j
Shohei Ohno, Ray Miyazaki, Tomoyuki Tanaka, Keita Uehara, Jiawei Qiu, Hirona Itakura, Makoto Sako, Kenichi Murai, Jun-ya Hasegawa, Mitsuhiro ARISAWA
{"title":"Diversity-Oriented Synthesis of Poly-substituted Benzofuran Derivatives Bearing Amino Groups at 2- or 3-Positions: Rh- or Ni-Catalyzed Cycloisomerization between Ynamides and Enol Ethers","authors":"Shohei Ohno, Ray Miyazaki, Tomoyuki Tanaka, Keita Uehara, Jiawei Qiu, Hirona Itakura, Makoto Sako, Kenichi Murai, Jun-ya Hasegawa, Mitsuhiro ARISAWA","doi":"10.1039/d5qo01123j","DOIUrl":"https://doi.org/10.1039/d5qo01123j","url":null,"abstract":"Amino-substituted benzofuran derivatives have attracted attention in recent years due to their remarkable biological activity. Synthetic methods for amino-substituted benzofuran derivatives have been reported, but these methods and the structural diversity of their products are limited. Herein, we report a divergent synthetic strategy for the efficient construction of amino-substituted benzofuran derivatives. We developed a novel rhodium- or nickel-catalyzed cycloisomerization between ynamides and enol ethers, enabling the selective synthesis of poly-substituted benzofuran derivatives bearing an amino group at either the 2- or 3-position from the same starting materials.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"78 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-09-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145103781","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
Gold-Catalyzed Spirocyclization of Activated Alkynes with Organoiodides: Access to 3-Arylated, 3-Alkenylated, and 3-Alkynylated Spiro[4.5]trienones 金催化活化炔烃与有机碘化合物的螺环化反应：获得3-芳基化、3-烯基化和3-炔基化的螺[4.5]三烯酮
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-09-22 DOI: 10.1039/d5qo01065a
Jianyue Bi, Zhenxing Zhang, Yuanhao He, Huajian Li, Xinming Yan, Fen Zhao, Fang Dai, Baomin Fan
{"title":"Gold-Catalyzed Spirocyclization of Activated Alkynes with Organoiodides: Access to 3-Arylated, 3-Alkenylated, and 3-Alkynylated Spiro[4.5]trienones","authors":"Jianyue Bi, Zhenxing Zhang, Yuanhao He, Huajian Li, Xinming Yan, Fen Zhao, Fang Dai, Baomin Fan","doi":"10.1039/d5qo01065a","DOIUrl":"https://doi.org/10.1039/d5qo01065a","url":null,"abstract":"Herein, we report the gold-catalyzed spirocyclization of activated alkynes with organoiodides through ligand-enabled gold redox catalysis. The reaction proceeds smoothly under mild conditions and without the need for an external oxidant, affording a series of 3-arylated, 3-alkenylated, and 3-alkynylated spiro[4.5]trienones in good to excellent yields. This transformation exhibits a broad substrate scope, good functional group tolerance, and compatibility with heteroaromatic systems. The (P,N) ligand MeDalphos-facilitated gold-catalyzed process provides a new strategy for the synthesis of 3-substituted spiro[4.5]trienones. Furthermore, mechanistic investigations, including NMR and mass spectrometric studies, strongly support the proposed reaction mechanism.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"317 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-09-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145103780","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
Cobaloxime Catalyzed Carbene Insertion into N–H Bonds: A Streamlined Route to α-Amino Esters with Mechanistic Insights 钴肟催化碳烯插入到N-H键：一个流线型的α-氨基酯的机制见解
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-09-22 DOI: 10.1039/d5qo01185j
Ke-Yang Wu, Kirklin L. McWhorter, Ayzia Ford, Liming Tan, Lidia M Waidmann, Jesus O Vazquez Hernandez, Madeline M Garcia, Katherine M Davis, Gang Li
{"title":"Cobaloxime Catalyzed Carbene Insertion into N–H Bonds: A Streamlined Route to α-Amino Esters with Mechanistic Insights","authors":"Ke-Yang Wu, Kirklin L. McWhorter, Ayzia Ford, Liming Tan, Lidia M Waidmann, Jesus O Vazquez Hernandez, Madeline M Garcia, Katherine M Davis, Gang Li","doi":"10.1039/d5qo01185j","DOIUrl":"https://doi.org/10.1039/d5qo01185j","url":null,"abstract":"The efficient construction of carbon–nitrogen bonds is fundamental to the synthesis of pharmaceuticals, agrochemicals, and natural products, particularly for α-amino esters. Transition-metal-catalyzed carbene insertion into N–H bonds offers a powerful approach due to its efficiency and selectivity, but has predominantly been developed using noble metal catalysts. Although, select base metals have been explored, cobalt catalysts remain scarce. Herein, we report an N–H insertion reaction to form α-amino esters catalyzed by a cobaloxime catalyst, using diazo compounds as the carbene precursors. With low catalyst loading, primary, secondary, and (hetero)aromatic amines all react smoothly (up to 97%). While comprehensive mechanistic studies suggest a cobalt alkyl ylide intermediate dominates these reactions, we observe small contributions of a carbene radical. This approach can be applied in the late-stage functionalization of various N-containing bioactive molecules, highlighting its potential synthetic application.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"60 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-09-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145103782","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
Visible light-promoted Pd-catalyzed regioselective 1,4-dicarbofunctionalization of 1,3-butadiene with unactivated bromides and malononitriles 可见光促进pd催化1,3-丁二烯与非活化溴和丙二腈的区域选择性1,4-二碳功能化
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-09-19 DOI: 10.1039/d5qo01117e
Mostafa Sayed, Xiao-Yun Ruan, Chenxi Wu, Ji-Feng Bai
{"title":"Visible light-promoted Pd-catalyzed regioselective 1,4-dicarbofunctionalization of 1,3-butadiene with unactivated bromides and malononitriles","authors":"Mostafa Sayed, Xiao-Yun Ruan, Chenxi Wu, Ji-Feng Bai","doi":"10.1039/d5qo01117e","DOIUrl":"https://doi.org/10.1039/d5qo01117e","url":null,"abstract":"As a versatile synthetic transformation, the dicarbofunctionalization of 1,3-butadiene enables the rapid assembly of structurally diverse allylic scaffolds. Herein, the selective 1,4-dicarbofunctionalization of 1,3-butadiene with organobromides (alkyl and aryl bromides) and malononitrile nucleophiles has been developed using a photoinduced Pd-catalyzed three-component coupling strategy. This process relies on photoexcited Pd(0) activation of both substrates through a single-electron transfer (SET) process, accommodating alkyl and aryl radicals of contrasting electronic character through precisely optimized reaction conditions. Under mild conditions, the protocol furnishes 74 functionalized malononitrile derivatives in high yields (up to 88%) and excellent regioselectivity (>20 : 1 rr), highlighting its broad scope and efficiency.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"109 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-09-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145084336","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 novel member of a benzo-annulated oxocarbon family 二苯环氧碳家族的新成员
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-09-18 DOI: 10.1039/d5qo01058f
Anna S. Rumyantseva, Konstantin Lyssenko, Tatiana V. Magdesieva
{"title":"A novel member of a benzo-annulated oxocarbon family","authors":"Anna S. Rumyantseva, Konstantin Lyssenko, Tatiana V. Magdesieva","doi":"10.1039/d5qo01058f","DOIUrl":"https://doi.org/10.1039/d5qo01058f","url":null,"abstract":"An unusual reactivity channel of semisquaraines is disclosed, yielding a novel type of oxocarbon derivative via facile synthetic procedure. The compound exhibits extremely rare “double” redox-ambipolarity (strong stabilization of both mono- and di- oppositely charged ionic states) sustained by a relatively small conjugated system. Remarkable “atom-economic” structure of the oxocarbon provides two orthogonal channels for charge/spin delocalization combined via the central 6-membered ring, which may be both in aromatic or in quinoidal state, thereby controlling charge redistribution and ensuring stabilization of five redox-states. Radical-cation shows no destruction in 24 h; half-life of the radical-anion is 2.5 h. Stability of multiple redox states in combination with intensive UV-Vis-NIR absorption gives rise to pronounced electrochromic behaviour that makes the novel oxocarbon derivative potentially interesting for application in electrochromic displays, in photovoltaics as well as a redox indicator, e.g., for sensing metal ions (shown experimentally). In the crystal state, the compound demonstrates high thermal stability and is prone to form π-stacked 1D supramolecular structure.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"16 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-09-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145077882","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 HFIP-promoted para-selective allylation of phenols via C–C bond activation of gem-difluorinated cyclopropanes 铜催化的hfip通过宝石二氟化环丙烷的C-C键激活促进了苯酚的对选择性烯丙基化
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-09-18 DOI: 10.1039/d5qo01197c
Xu Xu, Yilian Song, Wenhao Xu, Xiaoping Wang, Haitao Chen, Yingsheng Zhao
{"title":"Copper-catalyzed HFIP-promoted para-selective allylation of phenols via C–C bond activation of gem-difluorinated cyclopropanes","authors":"Xu Xu, Yilian Song, Wenhao Xu, Xiaoping Wang, Haitao Chen, Yingsheng Zhao","doi":"10.1039/d5qo01197c","DOIUrl":"https://doi.org/10.1039/d5qo01197c","url":null,"abstract":"Although ring-opening cross-coupling of <em>gem</em>-difluorocyclopropanes using transition metal catalysts is a well-explored strategy, the development of cost-effective metal catalysts for this transformation is still uncommon. This study presents a copper-catalyzed <em>para</em>-selective fluoroallylation of unprotected phenols achieved through a ring-opening cross-coupling approach. This straightforward method employs an inexpensive and easily accessible catalyst, offers a wide substrate scope, and supports late-stage functionalization of biologically active compounds. Mechanistic investigations suggest that an allyl–Cu(<small>III</small>) intermediate is generated through C–C bond oxidative addition to Cu(<small>I</small>), followed by C–F bond elimination. The <em>para</em>-selectivity is primarily attributed to hydrogen bonding between hexafluoroisopropanol and the phenol.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"126 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-09-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145077881","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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