Simone Galiè , Dr. Manar Ahmed Fouad , Cecilia Abbo , Prof. Francesco Ferretti , Prof. Fabio Ragaini
{"title":"Phenazines Synthesis by Palladium‐Catalyzed Reductive Cyclization of 2‐Nitro‐N‐Phenylanilines Using Gaseous CO or Its Surrogates","authors":"Simone Galiè , Dr. Manar Ahmed Fouad , Cecilia Abbo , Prof. Francesco Ferretti , Prof. Fabio Ragaini","doi":"10.1002/ajoc.202500555","DOIUrl":"10.1002/ajoc.202500555","url":null,"abstract":"<div><div>Phenazines are a diverse class of nitrogen‐containing heterocycles with a wide range of chemical structures and biological applications. We have developed a synthetic route for phenazines through a palladium‐catalyzed reductive cyclization of 2‐nitro‐<em>N</em>‐phenylanilines using either gaseous carbon monoxide or phenyl formate as an in situ CO source as efficient and cheap reductants. Our protocol offers a practical alternative to existing methods, achieving good yields without relying on large amounts of strongly reducing or oxidizing agents. Moreover, it minimizes the formation of unwanted byproducts, which is a common drawback in traditional phenazine synthesis. The key advantages of this protocol include the use of a simple Pd‐catalyst in the presence of 1,10‐phenanthroline (Phen), an inexpensive and commercially available ligand. These features make our method very convenient for phenazine synthesis. An uncommon inverse correlation between catalyst loading and product selectivity, as well as key differences between the use of gaseous CO and its surrogate, will also be discussed.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 10","pages":"Article e00555"},"PeriodicalIF":2.7,"publicationDate":"2025-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145316640","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}
Bertalan Varga , Katalin Németh , Dóra Ujj , Béla Mátravölgyi , Csaba Váradi , Zsolt Rapi
{"title":"The Structure‐Activity Relationship and Reusability of Chiral Azacrown Ethers Derived from L‐Threitol","authors":"Bertalan Varga , Katalin Németh , Dóra Ujj , Béla Mátravölgyi , Csaba Váradi , Zsolt Rapi","doi":"10.1002/ajoc.202500464","DOIUrl":"10.1002/ajoc.202500464","url":null,"abstract":"<div><div>In enantioselective reactions, several catalysts can be used, such as chiral crown ethers, which form a special group of them. In addition to the reaction conditions, the structure of the catalyst used also affects the outcome of the reaction. In the case of carbohydrate‐based crown ethers, we previously found that the monoaza‐15‐crown‐5 structure is the most effective, and the generated enantiomeric excess is influenced by the substituent of the nitrogen, the protecting groups of the carbohydrate, and the source of chirality. In this study, macrocycles derived from <span>l</span>‐threitol were synthesized with a similar structure, and their catalytic activity and reusability were tested and compared in different model reactions along with some previously prepared compounds. Several types of effect‐structure relationships were pointed out, while the enantiomeric excess varied widely. We demonstrated the recoverability of the crown ethers by acidic extraction and subsequent liberation of the azacrown moiety. The regeneration process was investigated more thoroughly in scaled‐up reactions, where the selectivity of the catalysts preserved for three examined cycles.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 10","pages":"Article e00464"},"PeriodicalIF":2.7,"publicationDate":"2025-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145317556","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}
Sijie Zhu , Huiyi Ren , Linsheng Ye , Ziqiang Cheng , Yuting Wang , Zheliang Yuan , Yanan Wang
{"title":"Tf2O‐Catalyzed Tandem Trifluoromethylselenolation/Cyclization of Alkenes for Synthesis of CF3Se‐Containing Heterocycles","authors":"Sijie Zhu , Huiyi Ren , Linsheng Ye , Ziqiang Cheng , Yuting Wang , Zheliang Yuan , Yanan Wang","doi":"10.1002/ajoc.202500586","DOIUrl":"10.1002/ajoc.202500586","url":null,"abstract":"<div><div>In this study, we have developed the tandem trifluoromethylselenolation/cyclization of alkenes to synthesize the CF<sub>3</sub>Se‐containing heterocycles with trifluoromethyl selenoxide as the trifluoromethylselenolation reagent and Tf<sub>2</sub>O as the catalyst. This transformation featured mild conditions and easy operation. Both CF<sub>3</sub>Se‐containing oxindoles and benzoxazines could be obtained in useful yields. Based on the preliminary results and previous reports, a mechanism involving the generation of the electrophilic CF<sub>3</sub>Se species was proposed.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 10","pages":"Article e00586"},"PeriodicalIF":2.7,"publicationDate":"2025-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145316867","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}
Haoxiang Zhang , Chaolin Li , Peiyuan Luo , Fei Ji , Changquan Zhang , Yuhan Jin , Yonghong Mi , Peng Liu , Qiyue Liu , Xiao Zhang
{"title":"Electrochemical Catalysis of Coupling Reaction between Diselenide / Disulfide and Diazonium Salt","authors":"Haoxiang Zhang , Chaolin Li , Peiyuan Luo , Fei Ji , Changquan Zhang , Yuhan Jin , Yonghong Mi , Peng Liu , Qiyue Liu , Xiao Zhang","doi":"10.1002/ajoc.202500549","DOIUrl":"10.1002/ajoc.202500549","url":null,"abstract":"<div><div>An electrochemically catalyzed coupling reaction of diselenides/disulfides with diazonium salts has been described. This method features short reaction time, mild conditions, low cost, high efficiency, and metal‐catalyst‐free operation, providing a novel route for synthesizing organoselenium compounds. Mechanistic studies such as cyclic voltammetry (CV), divided cell experiment, on–off electricity experiment, and radical trapping reactions support the electrochemical catalysis of the cross‐coupling process of diselenides with diazonium salts.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 10","pages":"Article e00549"},"PeriodicalIF":2.7,"publicationDate":"2025-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145317703","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}
Xinyu Ma , Ying Zhang , Prof. Dr. Congguang Zhang , Dr. Dharani Sivadasan , Prof. Dr. Hongmin Jia , Prof. Dr. Shao‐Tao Bai
{"title":"LiCl‐Promoted Branched Methoxycarbonylation of Propylene Using a Heterogenized Triphenylphosphine‐palladium Catalyst","authors":"Xinyu Ma , Ying Zhang , Prof. Dr. Congguang Zhang , Dr. Dharani Sivadasan , Prof. Dr. Hongmin Jia , Prof. Dr. Shao‐Tao Bai","doi":"10.1002/ajoc.202500569","DOIUrl":"10.1002/ajoc.202500569","url":null,"abstract":"<div><div>Branched selective carbonylation of propylene is a well‐known challenge for both academia and industry. In this study, we reported LiCl‐promoted branched selective methoxycarbonylation of propylene utilizing an easy heterogenized triphenylphosphine‐palladium catalyst (Pd/3V‐PPh<sub>3</sub>@POP). Various (heterogenized) ligands, additives, acids, and catalytic metals were tested. The catalyst Pd/3V‐PPh<sub>3</sub>@POP in the presence of LiCl gave a 36.9% increased branched selectivity at the expense of activity compared to the absence of additives (71.4% versus 34.5% branched selectivity, turnover numbers of 124.5 versus 421.8) under otherwise identical conditions. The optimal catalyst Pd/3V‐PPh<sub>3</sub>@POP was characterized using X‐ray diffraction (XRD), high‐angle annular dark field scanning transmission electron microscopy (HAADF‐STEM), scanning electron microscopy energy dispersive spectrometer (SEM‐EDS), Brunner–Emmet–Teller (BET), and thermogravimetric analysis (TGA) experiments and further tested in simple filtration recycling experiments using a continuous stirring reactor.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 10","pages":"Article e00569"},"PeriodicalIF":2.7,"publicationDate":"2025-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145317813","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}
Anna V. Listratova , Svetlana L. Chernikova , Angelina A. Sherchalova , Larisa N. Kulikova
{"title":"Versatility of Dialkyl Azodicarboxylates in Organic Transformations","authors":"Anna V. Listratova , Svetlana L. Chernikova , Angelina A. Sherchalova , Larisa N. Kulikova","doi":"10.1002/ajoc.202500459","DOIUrl":"10.1002/ajoc.202500459","url":null,"abstract":"<div><div>Dialkyl azodicarbixylates, characterized by the presence of an azo group (─N═N─) and two carboxyl groups, are an important class of organic compounds that have found wide application in organic synthesis, especially in Mitsunobu reaction. Their unique chemical properties make them irreplaceable tools for creating diverse molecular structures. This review provides an overview of key reactions involving dialkyl azodicarboxylates, highlighting their wide range of applications as reagents and catalysts. We also tried to demonstrate the immense potential of dialkyl azodicarboxylates in various types of reactions, including cross‐coupling, redox processes, cycloaddition, cyclizations, and functionalization of aromatic systems. The versatility of dialkyl azodicarboxylates makes them a valuable tool for building complex molecular structures and expanding the possibilities of synthetic chemistry.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 10","pages":"Article e00459"},"PeriodicalIF":2.7,"publicationDate":"2025-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145316945","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}
P. Naveen Reddy , Kiran Aswale , Rajashaker Bantu , B. Sridhar , B. V. Subba Reddy
{"title":"Benzo[d][1,3]Oxazine‐Assisted C─H Annulation of Arenes with Diarylacetylenes: Access to 3,4‐diarylisoquinolinones","authors":"P. Naveen Reddy , Kiran Aswale , Rajashaker Bantu , B. Sridhar , B. V. Subba Reddy","doi":"10.1002/ajoc.202500225","DOIUrl":"10.1002/ajoc.202500225","url":null,"abstract":"<div><div>A novel Rh(III)‐catalyzed [4 + 2] annulation of diarylacetylenes with 2‐aryl‐4<em>H</em>‐benzo[<em>d</em>][1,3]oxazines is described to produce a new class of 3,4‐diarylisoquinolinones through a ring‐opening C─H annulation of benzo[<em>d</em>][1,3]oxazine moiety. This is the first report on C─H functionalazation of 2‐aryl‐4H‐benzo[<em>d</em>][1,3]oxazines with diarylalkynes for the synthesis of 3,4‐diarylisoquinolinone scaffolds. The scope of this method is well exemplified with diverse substrates bearing different functional groups including electron‐rich and electron‐deficient substituents.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 10","pages":"Article e00225"},"PeriodicalIF":2.7,"publicationDate":"2025-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145317575","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}
Kun‐Hua Chiang , Meng‐De Wu , Prof. Dr. Kun‐Mu Lee , Prof. Dr. Ching‐Yuan Liu
{"title":"New Synthetic Pathway with Improvements and Optoelectronic Applications of 3,5‐Dihexyl‐dithienothiophene (DTT)","authors":"Kun‐Hua Chiang , Meng‐De Wu , Prof. Dr. Kun‐Mu Lee , Prof. Dr. Ching‐Yuan Liu","doi":"10.1002/ajoc.70154","DOIUrl":"10.1002/ajoc.70154","url":null,"abstract":"<div><div>A new synthetic route to 3,5‐dihexyl‐dithienothiophene (DTT) and related dithienoheteroaryls was reported. Unlike all existing approaches using costly sulfur‐supplying reagents (<em>S‐agent</em>), in this work inexpensive and readily available copper salt and elemental sulfur were employed as catalyst and <em>S‐agent</em> in the essential cyclization step, in which the reaction parameters were thoroughly optimized, giving targeted DTT in isolated yields up to 86%. Purification was not required after most of steps in this five‐step synthesis of dihexyl‐DTT. Gram‐scale synthesis of dihexyl‐DTT was also successfully achieved. Furthermore, π‐extension from DTT was facilely carried out either by direct C‐H/C‐Br couplings or the most succinct cross‐dehydrogenative C‐H/C‐H coupling reactions. The obtained oligoaryls <strong>KHC01</strong>–<strong>04</strong> were fabricated as effective hole‐transporting materials (HTM) for inverted perovskite solar cells (iPSC). Solar cell devices utilizing <strong>KHC03</strong> as HTM revealed promising power conversion efficiencies of up to 15.27%.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 10","pages":"Article e70154"},"PeriodicalIF":2.7,"publicationDate":"2025-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145317576","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}
{"title":"Carbon–Carbon/Heteroatom‐Centered Diradical Mediated Synthesis of Valuable Cyclic Motifs by EnT Catalyzed HAT Cyclization","authors":"Nirbhik Chatterjee","doi":"10.1002/ajoc.70170","DOIUrl":"10.1002/ajoc.70170","url":null,"abstract":"<div><div>Energy transfer (EnT) catalysis has emerged as a powerful and unique tool in modern synthetic methodology, enabling the generation of carbon–carbon/heteroatom centered diradicals from judiciously designed substrates. This highlight offers insights into recent breakthroughs including intramolecular cyclization, underscoring their potential to construct structurally complex, and valuable molecular architectures.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 10","pages":"Article e70170"},"PeriodicalIF":2.7,"publicationDate":"2025-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145317637","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}
{"title":"Photosulfonylation of Aryl Halides with Sodium Sulfinates Catalyzed by Heterogeneous Copper Polymers","authors":"Lijie Chen , Zhengbin Yun , Weiwei Fang","doi":"10.1002/ajoc.202500534","DOIUrl":"10.1002/ajoc.202500534","url":null,"abstract":"<div><div>A general method for photosulfonylation of aryl halides with sodium sulfinates was successfully developed by using reusable copper‐containing hyper‐cross‐linked polymers (HCPs‐Cu). These heterogeneous catalysts were easily prepared from molecular BINAP/Cu(MeCN)<sub>4</sub>PF<sub>6</sub> complex (BINAP‐Cu) with different amounts of benzene and formaldehyde dimethyl acetal (FDA) via direct knitting strategy, and the Cu center was uniformly dispersed in the matrices of HCPs‐Cu, featuring the same coordination environment to that of molecular BINAP‐Cu. This photosulfonylation system not only tolerates a wide range of substrates to furnish aryl sulfones, showing a potential in the synthesis of several drugs, but also highlights a moderate recyclability of 10 runs with minimal loss of catalytic activity.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 10","pages":"Article e00534"},"PeriodicalIF":2.7,"publicationDate":"2025-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145317704","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}