A hypervalent iodine‐mediated one‐step general method for the preparation of 2‐amino‐5‐acyl‐thiazoles and selenazoles has been disclosed. The reactions progress via umpolung cyclization of thio/seleno‐urea with enaminones. Mechanistically, the reaction progresses via C─N bond cleavage of enaminones rather than C═C bond.
{"title":"Iodine(III) Promoted Umpolung Cyclization of Thio/Seleno‐Urea With Enaminones: Preparation of 2‐Amino‐5‐acyl‐thiazoles/Selenazoles via C─N Bond Cleavage","authors":"Bal Krishna Mishra , Rohan Srivastava , Deepak Kumar , Bhoopendra Tiwari","doi":"10.1002/ajoc.202500624","DOIUrl":"10.1002/ajoc.202500624","url":null,"abstract":"<div><div>A hypervalent iodine‐mediated one‐step general method for the preparation of 2‐amino‐5‐acyl‐thiazoles and selenazoles has been disclosed. The reactions progress via umpolung cyclization of thio/seleno‐urea with enaminones. Mechanistically, the reaction progresses via C─N bond cleavage of enaminones rather than C═C bond.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"15 1","pages":"Article e00624"},"PeriodicalIF":2.7,"publicationDate":"2026-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145891120","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}
Pub Date : 2026-01-01Epub Date: 2025-12-07DOI: 10.1002/ajoc.70266
Xin Zhao , Jinglong Qi , Zongle Shen , Lintao Qu , Haoyang Li , Chentong Sun , Chang Wang , Xuemei Zhao
Novel copper‐catalyzed [4 + 1] annulation synthesizes spiro‐cyclopentanes using bis‐electrophilic Cu‐aminoallyl cations (from EMCCs) and activated methylene dinucleophiles. The methodology exhibits broad substrate scope, accommodating EMCCs with electron‐donating/withdrawing aryl groups /alkyl chains, and various activated methylene partners, providing a versatile alternative to construct spiro‐cyclopentane via conventional [3 + 2] cycloadditions.
{"title":"The Copper‐Catalyzed [4 + 1] Annulation of Ethynyl Methylene Cyclic Carbamates With Various Activated Methylene Compounds to Construct Spiro‐Cyclopentane Derivatives","authors":"Xin Zhao , Jinglong Qi , Zongle Shen , Lintao Qu , Haoyang Li , Chentong Sun , Chang Wang , Xuemei Zhao","doi":"10.1002/ajoc.70266","DOIUrl":"10.1002/ajoc.70266","url":null,"abstract":"<div><div>Novel copper‐catalyzed [4 + 1] annulation synthesizes spiro‐cyclopentanes using bis‐electrophilic Cu‐aminoallyl cations (from EMCCs) and activated methylene dinucleophiles. The methodology exhibits broad substrate scope, accommodating EMCCs with electron‐donating/withdrawing aryl groups /alkyl chains, and various activated methylene partners, providing a versatile alternative to construct spiro‐cyclopentane via conventional [3 + 2] cycloadditions.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"15 1","pages":"Article e70266"},"PeriodicalIF":2.7,"publicationDate":"2026-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145891115","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}
Pub Date : 2026-01-01Epub Date: 2025-12-07DOI: 10.1002/ajoc.70271
Shiyun Li , Yan An , Lulu Wang , Xin Li , Yao Tan , Bin Wen , Tiesen Li , Xingquan Chen
A highly efficient electrochemical oxidative dehydrogenative N–N coupling of arylamines to selectively provide benzo[c]cinnolines and azoarenes has been investigated. In this simple process, various functional groups were tolerated under mild reaction conditions without additional metal or oxidant, and the practicality of the protocol was demonstrated by the preparation of benzo[c]cinnolines on a gram scale and later derivatization. Mechanism of studies shows that the reaction proceeds via a radical pathway with the hydrazine compound as an intermediate. Additionally, the base plays an important role in this transformation, potentially facilitating the dehydrogenation process.
{"title":"Electrochemical Oxidative N–N Coupling to Construct Benzo[c]cinnolines and Azoarenes","authors":"Shiyun Li , Yan An , Lulu Wang , Xin Li , Yao Tan , Bin Wen , Tiesen Li , Xingquan Chen","doi":"10.1002/ajoc.70271","DOIUrl":"10.1002/ajoc.70271","url":null,"abstract":"<div><div>A highly efficient electrochemical oxidative dehydrogenative N–N coupling of arylamines to selectively provide benzo[<em>c</em>]cinnolines and azoarenes has been investigated. In this simple process, various functional groups were tolerated under mild reaction conditions without additional metal or oxidant, and the practicality of the protocol was demonstrated by the preparation of benzo[<em>c</em>]cinnolines on a gram scale and later derivatization. Mechanism of studies shows that the reaction proceeds via a radical pathway with the hydrazine compound as an intermediate. Additionally, the base plays an important role in this transformation, potentially facilitating the dehydrogenation process.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"15 1","pages":"Article e70271"},"PeriodicalIF":2.7,"publicationDate":"2026-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145887828","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}
Pub Date : 2026-01-01Epub Date: 2025-12-07DOI: 10.1002/ajoc.70274
Dandan Zhao , Hongyan Yang , Xiaoli Wang , Peng He , Yanli Xu , Qifu Lin
A highly efficient iridium‐catalyzed ring‐opening reactions of heterobicyclic alkenes with fluoroalkyl alcohols has been developed. The reaction utilizes readily available fluoroalkyl alcohols as fluoroalkoxylation reagents and exhibits a wide substrate scope, affording the fluoroalkoxylated products with trans‐1,2‐disubstituted dihydronaphthalene framework in good to excellent yields. Mechanistic insights, supported by computational studies, have been proposed to elucidate the reaction pathway.
{"title":"Iridium‐Catalyzed Anti‐Stereoselective Ring‐Opening Fluoroalkoxylation of Heterobicyclic Alkenes","authors":"Dandan Zhao , Hongyan Yang , Xiaoli Wang , Peng He , Yanli Xu , Qifu Lin","doi":"10.1002/ajoc.70274","DOIUrl":"10.1002/ajoc.70274","url":null,"abstract":"<div><div>A highly efficient iridium‐catalyzed ring‐opening reactions of heterobicyclic alkenes with fluoroalkyl alcohols has been developed. The reaction utilizes readily available fluoroalkyl alcohols as fluoroalkoxylation reagents and exhibits a wide substrate scope, affording the fluoroalkoxylated products with <em>trans</em>‐1,2‐disubstituted dihydronaphthalene framework in good to excellent yields. Mechanistic insights, supported by computational studies, have been proposed to elucidate the reaction pathway.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"15 1","pages":"Article e70274"},"PeriodicalIF":2.7,"publicationDate":"2026-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145891121","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}
Pub Date : 2026-01-01Epub Date: 2025-12-09DOI: 10.1002/ajoc.70276
Wenjing Liu , Feng Zhao
A practical and efficient potassium trimethylsilanolate/nitrile system for constructing all‐carbon quaternary centers has been developed. This transition‐metal free protocol utilizes readily available chlorides and 1,3‐dicarbonyl compounds, enabling the selective formation of two C─C bonds in a single operation. The reaction features broad substrate scope, good functional group tolerance, large scale synthesis, and further structural modification, providing a mild approach to access quaternary centers in moderate to excellent yields.
{"title":"Transition‐Metal Free Dialkylation to Construct All‐Carbon Quaternary Centers From Alkyl Chlorides and 1,3‐Dicarbonyl Compounds","authors":"Wenjing Liu , Feng Zhao","doi":"10.1002/ajoc.70276","DOIUrl":"10.1002/ajoc.70276","url":null,"abstract":"<div><div>A practical and efficient potassium trimethylsilanolate/nitrile system for constructing all‐carbon quaternary centers has been developed. This transition‐metal free protocol utilizes readily available chlorides and 1,3‐dicarbonyl compounds, enabling the selective formation of two C─C bonds in a single operation. The reaction features broad substrate scope, good functional group tolerance, large scale synthesis, and further structural modification, providing a mild approach to access quaternary centers in moderate to excellent yields.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"15 1","pages":"Article e70276"},"PeriodicalIF":2.7,"publicationDate":"2026-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145891455","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}
Pub Date : 2026-01-01Epub Date: 2026-02-03DOI: 10.1002/ajoc.70311
Yatharth Joshi , Manorama Singh , Ankita Rai , Vijai K. Rai
The organic compounds containing guanidine moieties are known to show several applications in the field of medicines, catalysts, and polymers, etc. The use of guanidines has been explored by researchers all over the world. Guanidines serve as an important tool in the synthesis of heterocycles, which serve as therapeutic agents and also show a wide array of applications. Due to their cost efficiency, atom economy, and eco‐friendliness, Multicomponent reactions (MCRs) have drawn the attention of researchers and scientists all over the world. This review highlights the applications of guanidines as a reagent as well as a catalyst in synthesizing various heterocyclic scaffolds via one‐pot Multicomponent reactions.
{"title":"Y‐Aromatic Guanidines as Steering Reagent in Multicomponent Heterocyclic Syntheses","authors":"Yatharth Joshi , Manorama Singh , Ankita Rai , Vijai K. Rai","doi":"10.1002/ajoc.70311","DOIUrl":"10.1002/ajoc.70311","url":null,"abstract":"<div><div>The organic compounds containing guanidine moieties are known to show several applications in the field of medicines, catalysts, and polymers, etc. The use of guanidines has been explored by researchers all over the world. Guanidines serve as an important tool in the synthesis of heterocycles, which serve as therapeutic agents and also show a wide array of applications. Due to their cost efficiency, atom economy, and eco‐friendliness, Multicomponent reactions (MCRs) have drawn the attention of researchers and scientists all over the world. This review highlights the applications of guanidines as a reagent as well as a catalyst in synthesizing various heterocyclic scaffolds via one‐pot Multicomponent reactions.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"15 1","pages":"Article e70311"},"PeriodicalIF":2.7,"publicationDate":"2026-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146049386","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}
Optically active 2‐azatriptycene 1 bearing a 1‐pyrenyl unit was synthesized. The resolved enantiomers exhibited blue circularly polarized luminescence (CPL) in solution, with dissymmetry factor glum on the order of 10−4–10−5. In contrast, the corresponding protonated species 1H+ exhibited green CPL with reversed sign, demonstrating that optically active 2‐azatriptycene functions as an acid‐responsive chiral switching unit.
{"title":"Optically Active 2‐Azatriptycene Bearing a 1‐Pyrenyl Unit Exhibiting Acid‐Induced CPL Switching With Sign Inversion","authors":"Yusuke Hashimoto , Ryo Inoue , Masayuki Gon , Kazuo Tanaka , Norihiro Aiga , Satoshi Takeuchi , Kazuya Kubo , Tomohiro Agou","doi":"10.1002/ajoc.70297","DOIUrl":"10.1002/ajoc.70297","url":null,"abstract":"<div><div>Optically active 2‐azatriptycene <strong>1</strong> bearing a 1‐pyrenyl unit was synthesized. The resolved enantiomers exhibited blue circularly polarized luminescence (CPL) in solution, with dissymmetry factor <em>g</em><sub>lum</sub> on the order of 10<sup>−4</sup>–10<sup>−5</sup><sub>.</sub> In contrast, the corresponding protonated species <strong>1H</strong><sup>+</sup> exhibited green CPL with reversed sign, demonstrating that optically active 2‐azatriptycene functions as an acid‐responsive chiral switching unit.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"15 1","pages":"Article e70297"},"PeriodicalIF":2.7,"publicationDate":"2026-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146002342","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}
Pub Date : 2026-01-01Epub Date: 2026-02-03DOI: 10.1002/ajoc.70299
Xuehua Zhang , Jie Gao , Binyu He , Mengtian Dong , Tiankai Zhang , Jun Dong , Feng Chen
This work presents a visible‐light‐driven annulation protocol for synthesizing 6‐silylphenanthridines from 2‐isocyanobiaryls and silanes using mesoporous graphitic carbon nitride (mpg‐CN) as a heterogeneous photocatalyst. The mpg‐CN catalyst demonstrates exceptional recyclability, maintaining consistent activity over five consecutive cycles without loss of performance. Operating under ambient conditions without requiring precious metals or expensive organic photo redox catalysts, this method offers mild reaction conditions, cost efficiency, and operational simplicity. The protocol provides a scalable and sustainable approach to accessing 6‐silyl‐substituted phenanthridines, highlighting the potential of heterogeneous photocatalysis in organic synthesis.
{"title":"mpg‐CN Photo‐Catalyzed Annulation of 2‑Isocyanobiaryls With Silanes to 6‑Silyl‐Substituted Phenanthridines","authors":"Xuehua Zhang , Jie Gao , Binyu He , Mengtian Dong , Tiankai Zhang , Jun Dong , Feng Chen","doi":"10.1002/ajoc.70299","DOIUrl":"10.1002/ajoc.70299","url":null,"abstract":"<div><div>This work presents a visible‐light‐driven annulation protocol for synthesizing 6‐silylphenanthridines from 2‐isocyanobiaryls and silanes using mesoporous graphitic carbon nitride (mpg‐CN) as a heterogeneous photocatalyst. The mpg‐CN catalyst demonstrates exceptional recyclability, maintaining consistent activity over five consecutive cycles without loss of performance. Operating under ambient conditions without requiring precious metals or expensive organic photo redox catalysts, this method offers mild reaction conditions, cost efficiency, and operational simplicity. The protocol provides a scalable and sustainable approach to accessing 6‐silyl‐substituted phenanthridines, highlighting the potential of heterogeneous photocatalysis in organic synthesis.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"15 1","pages":"Article e70299"},"PeriodicalIF":2.7,"publicationDate":"2026-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146002062","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}
Pub Date : 2026-01-01Epub Date: 2026-02-03DOI: 10.1002/ajoc.70294
Divya Shrestha , Karuna Mahato , Prasanta Roy , Seung Woo Lee , Yong Rok Lee
Maleimide‐containing molecules serve as important scaffolds for biological activities as well as photochemical properties and play a significant role in both the academic and industrial communities. Maleimides are versatile coupling partners owing to their diverse reactivities with transition‐metal catalysts in C–H activation and annulation reactions including alkenylation, alkylation, fused‐annulation, and spiro‐annulation for the synthesis of numerous maleimide‐containing bioactive molecules such as succinamides, lactams, and lactims. In this review, innovative advances toward the synthesis of biologically important maleimide/succinimide‐bearing scaffolds through C–H activation and annulation reactions with transition metal as catalysts, with particular emphasis on the intermediates, transition states, and incorporation of different annulation sites for maleimide is reviewed. This review covers research published between 2019 and 2025, highlighting the substrate scope, reaction mechanisms, synthetic transformations, and future prospects of this approach.
{"title":"Maleimides as Versatile Reactive Platforms in Transition‐Metal‐Catalyzed C–H Activation/Annulation","authors":"Divya Shrestha , Karuna Mahato , Prasanta Roy , Seung Woo Lee , Yong Rok Lee","doi":"10.1002/ajoc.70294","DOIUrl":"10.1002/ajoc.70294","url":null,"abstract":"<div><div>Maleimide‐containing molecules serve as important scaffolds for biological activities as well as photochemical properties and play a significant role in both the academic and industrial communities. Maleimides are versatile coupling partners owing to their diverse reactivities with transition‐metal catalysts in C–H activation and annulation reactions including alkenylation, alkylation, fused‐annulation, and spiro‐annulation for the synthesis of numerous maleimide‐containing bioactive molecules such as succinamides, lactams, and lactims. In this review, innovative advances toward the synthesis of biologically important maleimide/succinimide‐bearing scaffolds through C–H activation and annulation reactions with transition metal as catalysts, with particular emphasis on the intermediates, transition states, and incorporation of different annulation sites for maleimide is reviewed. This review covers research published between 2019 and 2025, highlighting the substrate scope, reaction mechanisms, synthetic transformations, and future prospects of this approach.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"15 1","pages":"Article e70294"},"PeriodicalIF":2.7,"publicationDate":"2026-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145983614","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}
Pub Date : 2026-01-01Epub Date: 2026-02-03DOI: 10.1002/ajoc.202500630
Arjun Gontala , Hanifah Mardhiyah , Sang Kook Woo
A mild, efficient, and sustainable photoredox method has been developed for the synthesis of β‐aminosulfides and β‐aminosulfoxides. The transformation employs imines as readily available radical acceptors and organosilicon reagents as radical precursors, providing the desired products in good yields across a broad substrate scope. A one‐pot aerobic oxidation sequence was also established, enabling direct access to β‐aminosulfoxides under photocatalytic conditions with oxygen as the terminal oxidant. Mechanistic studies, including cyclic voltammetry, luminescence quenching, and radical inhibition experiments, revealed that α‐thiomethyl radicals are generated through a single‐electron transfer (SET) process, and that both SET and energy transfer (EnT) pathways contribute to the aerobic oxidation step.
{"title":"Visible‐Light Photoredox‐Catalyzed Synthesis of β‐Aminosulfides and β‐Aminosulfoxides via Radical Addition to Imines","authors":"Arjun Gontala , Hanifah Mardhiyah , Sang Kook Woo","doi":"10.1002/ajoc.202500630","DOIUrl":"10.1002/ajoc.202500630","url":null,"abstract":"<div><div>A mild, efficient, and sustainable photoredox method has been developed for the synthesis of β‐aminosulfides and β‐aminosulfoxides. The transformation employs imines as readily available radical acceptors and organosilicon reagents as radical precursors, providing the desired products in good yields across a broad substrate scope. A one‐pot aerobic oxidation sequence was also established, enabling direct access to β‐aminosulfoxides under photocatalytic conditions with oxygen as the terminal oxidant. Mechanistic studies, including cyclic voltammetry, luminescence quenching, and radical inhibition experiments, revealed that α‐thiomethyl radicals are generated through a single‐electron transfer (SET) process, and that both SET and energy transfer (EnT) pathways contribute to the aerobic oxidation step.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"15 1","pages":"Article e00630"},"PeriodicalIF":2.7,"publicationDate":"2026-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145983510","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}
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