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Mn(I)‐Catalyzed C−H Allylation of Indoles with 2‐Vinylaziridines
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-01-01 DOI: 10.1002/ajoc.202400467
Hong Zeng , Zhong‐Xia Wang
{"title":"Mn(I)‐Catalyzed C−H Allylation of Indoles with 2‐Vinylaziridines","authors":"Hong Zeng ,&nbsp;Zhong‐Xia Wang","doi":"10.1002/ajoc.202400467","DOIUrl":"10.1002/ajoc.202400467","url":null,"abstract":"<div><div>Mn(CO)<sub>5</sub>Br‐catalyzed reaction of 1‐(2‐pyrimidyl)indoles with 1‐sulfonyl‐2‐vinylaziridines in THF in the presence of 0.25 equiv. of NaOAc affords 2‐allylated indoles in 31 % to 100 % yields. The protocol suits for 3‐, 4‐, 5‐, 6‐, and 7‐substituted indoles and N‐(2‐pyrimidyl)pyrroles as well as various 1‐(arylsulfonyl)‐2‐vinylaziridines such as 1‐(phenylsulfonyl)‐2‐vinylaziridine, 1‐(naphthalen‐2‐ylsulfon‐yl)‐2‐vinylaziridine, and 1‐(substituted phenylsulfonyl)‐2‐vinylazirid‐ines. Functional groups including alkyl, alkoxy, halogen, CHO, COOMe, CF<sub>3</sub>, CN, and NO<sub>2</sub> groups are tolerated.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 1","pages":"Article e202400467"},"PeriodicalIF":2.8,"publicationDate":"2025-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143113572","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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 of 3‐Acyl‐1‐Indenones by Oxidative Cyclization of Symmetrical and Unsymmetrical Aryldiynes Using Palladium Nanoparticles (Pd‐BNP) as Reusable Nano Catalyst
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-01-01 DOI: 10.1002/ajoc.202400260
Gollapalli Narasimha Rao , Krishnamoorthy Kathirvel , Govindasamy Sekar
{"title":"Synthesis of 3‐Acyl‐1‐Indenones by Oxidative Cyclization of Symmetrical and Unsymmetrical Aryldiynes Using Palladium Nanoparticles (Pd‐BNP) as Reusable Nano Catalyst","authors":"Gollapalli Narasimha Rao ,&nbsp;Krishnamoorthy Kathirvel ,&nbsp;Govindasamy Sekar","doi":"10.1002/ajoc.202400260","DOIUrl":"10.1002/ajoc.202400260","url":null,"abstract":"<div><div>An efficient, stable and reusable binaphthyl stabilized palladium nanoparticles (Pd‐BNP) catalyzed synthesis of 3‐acyl‐1‐indenone derivatives from oxidative cyclization of symmetrical and unsymmetrical aryldiynes using DMSO as a solvent as well as an oxidant has been established. The scope of the reaction has been studied with various aryldiynes having electron‐donating and electron‐withdrawing groups that afforded good yields. Pd‐BNP catalyst can be recovered and reused for up to four cycles without major changes in particle size and reactivity.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 1","pages":"Article e202400260"},"PeriodicalIF":2.8,"publicationDate":"2025-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143114448","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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 on Organic Electron Donors (OEDs) Enabled Radical Reactions
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-01-01 DOI: 10.1002/ajoc.202400520
Yu Shao , Xiaodong Jia
{"title":"Recent Progress on Organic Electron Donors (OEDs) Enabled Radical Reactions","authors":"Yu Shao ,&nbsp;Xiaodong Jia","doi":"10.1002/ajoc.202400520","DOIUrl":"10.1002/ajoc.202400520","url":null,"abstract":"<div><div>Over the past few decades, organic transformations facilitated by small organic molecules have witnessed considerable advancements. Small organic molecules have been widely applied to the construction of various skeletons. However, reduction as one of the fundamental reactions is generally initiated by metal‐containing reducing agents, although the initial progress of organic electron donors (OEDs) enabled reductive cleavage of some chemical bonds had been achieved in 1990s. Due to their structural diversity and tunability, OEDs can overcome the limitations of metal‐based reducing agents, such as low selectivity and poor functional group tolerance as well as the environmental problems caused by substantial inorganic waste after reactions. Building on a brief historical overview of OED research, this review focuses on the rencent advancements of the OEDs promoted radical reactions. It covers the reduction of C−X (X=C, O, N etc.) single bonds, radical cyclization, intermolecular radical addition to unsaturated bonds, radical coupling, functionalization of aromatics, and C−H bond activation. Additionally, the mechanistic insights of the typical reactions are highlighted for well understanding of the reaction mode involving OEDs.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 1","pages":"Article e202400520"},"PeriodicalIF":2.8,"publicationDate":"2025-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143117904","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
DFT Study in an Asymmetric Organocatalytic Homologation: Mechanism, Origin of Stereoselectivity
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-01-01 DOI: 10.1002/ajoc.202400504
Yang Wang , Donghui Wei
{"title":"DFT Study in an Asymmetric Organocatalytic Homologation: Mechanism, Origin of Stereoselectivity","authors":"Yang Wang ,&nbsp;Donghui Wei","doi":"10.1002/ajoc.202400504","DOIUrl":"10.1002/ajoc.202400504","url":null,"abstract":"<div><div>In the present study, the mechanism, origin of stereoselectivity, and role of catalyst of the organocatalytic homologation reaction between phenyl boronate and trifluoromethyl diazomethane have been theoretically investigated using the density functional theory (DFT) method. Based on the calculations, the <em>in situ</em> generated ethanol plays significant role in triggering the reaction. Moreover, the [1,2]‐boron migration process is the stereoselectivity‐determining step, with the <em>S</em>‐configured isomer being generated predominantly. In addition, NCI analysis is performed to disclose the origin of stereoselectivity.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 1","pages":"Article e202400504"},"PeriodicalIF":2.8,"publicationDate":"2025-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143118506","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Ruthenium Catalysed Transfer Deuteration of Heteroaromatics in D2O
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-01-01 DOI: 10.1002/ajoc.202400462
Carlos Gonzalo‐Navarro , Margarita Ruiz‐Castañeda , Jairo Fidalgo , Gustavo Espino , Félix A. Jalón , Blanca R. Manzano
{"title":"Ruthenium Catalysed Transfer Deuteration of Heteroaromatics in D2O","authors":"Carlos Gonzalo‐Navarro ,&nbsp;Margarita Ruiz‐Castañeda ,&nbsp;Jairo Fidalgo ,&nbsp;Gustavo Espino ,&nbsp;Félix A. Jalón ,&nbsp;Blanca R. Manzano","doi":"10.1002/ajoc.202400462","DOIUrl":"10.1002/ajoc.202400462","url":null,"abstract":"<div><div>There is a growing interest in deuterated derivatives in various fields, including the pharmaceutical industry. In this industry, partially hydrogenated heterocycles are also a target. Combining these two concepts, it was studied the reduction of heterocycles with simultaneous deuterium incorporation by transfer deuteration, a process of introducing two deuterium atoms into an organic molecule using non‐D<sub>2</sub> sources, avoiding the use of a gas or harmful reagents. Formic acid/sodium formate and D<sub>2</sub>O as the sole deuterium source were used under mild conditions. The precatalyst was [RuCl(<em>p</em>‐cym)(dmbpy)]BF<sub>4</sub>, (<em>p</em>‐cym=<em>p</em>‐cymene, dmbpy=4,4’‐dimethyl‐2,2’‐bipyridine), which is able to generate the “Ru−D” fragment from D<sup>+</sup> by a polarity inversion process (“umpolung”). A wide range of heterocycles were tested. Selective reduction in the nitrogen‐containing ring with deuterium incorporation into the same ring was achieved. The experiments were carried out in a biphasic D<sub>2</sub>O/toluene medium, which allowed excellent catalyst recycling with a simple work‐up. Through detailed studies for 3‐methylquinoline using DCOOD/DCOONa, the reaction mechanism that involves D<sup>+</sup> incorporation at the nitrogen atom and an initial 1,2‐type addition was elucidated. In single‐phase D<sub>2</sub>O experiments, a distinct selectivity with deuterium incorporation in the non‐hydrogenated ring was observed thus enabling to modulate it by the choice of the medium.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 1","pages":"Article e202400462"},"PeriodicalIF":2.8,"publicationDate":"2025-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ajoc.202400462","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143119174","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Palladium‐Catalyzed (4+2) Annulations of Silacyclobutanes and Activated Ketones
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-01-01 DOI: 10.1002/ajoc.202400536
Zhao‐Li Song , Jia‐Le Zheng , Zhi‐Chao Chen , Wei Du , Zhenlei Song , Ying‐Chun Chen
{"title":"Palladium‐Catalyzed (4+2) Annulations of Silacyclobutanes and Activated Ketones","authors":"Zhao‐Li Song ,&nbsp;Jia‐Le Zheng ,&nbsp;Zhi‐Chao Chen ,&nbsp;Wei Du ,&nbsp;Zhenlei Song ,&nbsp;Ying‐Chun Chen","doi":"10.1002/ajoc.202400536","DOIUrl":"10.1002/ajoc.202400536","url":null,"abstract":"<div><div>Presented herein is a palladium‐catalyzed (4+2) annulation reaction between silacyclobutanes and activated ketones, which features advantages of operation simplicity, broad substrate scope and good functionality tolerance. A diversity of oxasilacyclohexanes were straightforwardly constructed in high yields.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 1","pages":"Article e202400536"},"PeriodicalIF":2.8,"publicationDate":"2025-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143120266","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Ru(II)‐catalyzed ortho C−H Arylation of Heterocyclic Biaryls
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-01-01 DOI: 10.1002/ajoc.202400463
Erick M. C. Pinheiro , Daniel P. Couto , Caio C. Oliveira
{"title":"Ru(II)‐catalyzed ortho C−H Arylation of Heterocyclic Biaryls","authors":"Erick M. C. Pinheiro ,&nbsp;Daniel P. Couto ,&nbsp;Caio C. Oliveira","doi":"10.1002/ajoc.202400463","DOIUrl":"10.1002/ajoc.202400463","url":null,"abstract":"<div><div>Ru(II)‐Pheox complexes are known catalysts for carbene insertion reactions. Herein we teach them a new trick: how to perform <em>ortho</em> C−H arylation processes! Our operationally simple protocol tolerates structurally diverse directing groups and both aryl iodides and diaryliodonium salts as transfer groups.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 1","pages":"Article e202400463"},"PeriodicalIF":2.8,"publicationDate":"2025-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143112003","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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, Chiroptical Properties, and Absolute Configuration Determination of Phenyl‐4‐pyridyl‐2,5‐dipyrimidinylmethane
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-01-01 DOI: 10.1002/ajoc.202400577
Kouzou Matsumoto , Rina Tanaka , Kaori Miki , Akihito Konishi , Hiroyuki Kurata , Takashi Kubo , Gennaro Pescitelli , Koichi Matsuo , Tatsuo Nehira
{"title":"Synthesis, Chiroptical Properties, and Absolute Configuration Determination of Phenyl‐4‐pyridyl‐2,5‐dipyrimidinylmethane","authors":"Kouzou Matsumoto ,&nbsp;Rina Tanaka ,&nbsp;Kaori Miki ,&nbsp;Akihito Konishi ,&nbsp;Hiroyuki Kurata ,&nbsp;Takashi Kubo ,&nbsp;Gennaro Pescitelli ,&nbsp;Koichi Matsuo ,&nbsp;Tatsuo Nehira","doi":"10.1002/ajoc.202400577","DOIUrl":"10.1002/ajoc.202400577","url":null,"abstract":"<div><div>Phenyl‐4‐pyridyl‐2,5‐dipyrimidinylmethane (<strong>1</strong>) has been synthesized in five steps from 5‐methylpyrimidine. The structural feature of <strong>1</strong> is the symmetry elements with respect to the 180° rotation of the aryl group along the central C−C bonds. Due to this structural feature, the compound <strong>1</strong> is expected the good crystallinity despite of the asymmetric molecular structure. The optical resolution of <strong>1</strong> was achieved by high performance liquid chromatography using chiral stationary phase (chiral HPLC). The circular dichroism (CD) spectra of the two fractions showed opposite signs. As expected, the X‐ray crystallographic analysis was successfully performed for both the racemic and enantiomerically pure crystals of <strong>1</strong>, with the nitrogen atoms being unambiguously assigned in both cases. It was concluded the first‐eluted fraction in chiral HPLC was determined to be <em>S</em> configuration both by the CD calculation for reproducing the experimental CD spectrum and by the anomalous diffraction of X‐ray crystallographic analysis of enantiomerically pure <strong>1</strong>.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 1","pages":"Article e202400577"},"PeriodicalIF":2.8,"publicationDate":"2025-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143113151","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Functional 1,2,4,5‐Tetrazine Systems for Photocatalysis and Sensing
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-01-01 DOI: 10.1002/ajoc.202400553
K. Aswani Raj , M. Rajeswara Rao
{"title":"Functional 1,2,4,5‐Tetrazine Systems for Photocatalysis and Sensing","authors":"K. Aswani Raj ,&nbsp;M. Rajeswara Rao","doi":"10.1002/ajoc.202400553","DOIUrl":"10.1002/ajoc.202400553","url":null,"abstract":"<div><div>s‐Tetrazines are aromatic heterocyclic systems with distinct structural and optoelectronic features, which have led to the design and development of tetrazine‐derived systems in various applications. In this review, we summarize all the research reported on the subject of the applicability of tetrazine derivatives for photocatalytic chemical transformation, hydrogen production, and coordination‐based analyte detection.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 1","pages":"Article e202400553"},"PeriodicalIF":2.8,"publicationDate":"2025-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143114351","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Caboxylative Coupling of N‐(Arylmethyl)sulfonimides with Allyltributylstannane Catalyzed by Palladium Nanoparticles Involving Benzylic C−N Cleavage
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-01-01 DOI: 10.1002/ajoc.202400388
Chaolin Wu , Yanlong Xie , Dr. Jiliang Song , Prof. Xiujuan Feng , Siqi Jian , Wenchao Lu , Jiuzhen Zhu , Prof. Yoshinori Yamamoto , Prof. Ming Bao
{"title":"Caboxylative Coupling of N‐(Arylmethyl)sulfonimides with Allyltributylstannane Catalyzed by Palladium Nanoparticles Involving Benzylic C−N Cleavage","authors":"Chaolin Wu ,&nbsp;Yanlong Xie ,&nbsp;Dr. Jiliang Song ,&nbsp;Prof. Xiujuan Feng ,&nbsp;Siqi Jian ,&nbsp;Wenchao Lu ,&nbsp;Jiuzhen Zhu ,&nbsp;Prof. Yoshinori Yamamoto ,&nbsp;Prof. Ming Bao","doi":"10.1002/ajoc.202400388","DOIUrl":"10.1002/ajoc.202400388","url":null,"abstract":"<div><div>The palladium‐catalyzed three‐component coupling of aryl (hetero) methylsulfonamide, allyltributyltin and carbon dioxide (carboxylative Stille coupling reaction) was successfully conduced to produce <em>β</em>,<em>γ</em>‐unsaturated esters in satisfactory to good yields. The reaction was carried out under mild conditions by using in situ generated palladium nanoparticles as catalyst through the formation of π‐allylpalladium sulfonamide intermediates in the presence of tetrabutylammonium bromide (TBAB).</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 1","pages":"Article e202400388"},"PeriodicalIF":2.8,"publicationDate":"2025-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143115160","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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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