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}
Lin Shi , Pengyu Liang , Zhou Sun , Liangchen Xie , Ruoxuan Sun , Na Zhao , LiZeng Peng , Xiaojun Yao
A BF3·Et2O‐promoted cascade annulation of 2‐propynolphenols is described for the synthesis of 2‐substituted 3‐sulfenylbenzofurans. This protocol was achieved through a sequential Meyer–Schuster rearrangement/nucleophilic addition/intramolecular annulation sequence. Mechanistic studies and density functional theory (DFT) calculations provided robust support for the proposed reaction pathway and identified the combined process of the ring‐closing step and the hydrogen transfer process as the rate‐determining step. This method provides an efficient route to C─S bond formation for the assembly of a wide range of 3‐sulfenylbenzofurans in excellent yields under mild conditions. The screening of these 3‐sulfenylbenzofurans against four human cancer cell lines indicated their excellent anticancer activities, wherein compound 3y strongly inhibited prostate cancer cells, with a half‐maximal inhibitory concentration value of 7.24 ± 0.45 µM.
{"title":"BF3·Et2O‐Promoted Annulation of 2‐Propynolphenols With Thiophenols to Yield 2‐Substituted 3‐Sulfenylbenzofurans With Anti‐Prostate Cancer Activities","authors":"Lin Shi , Pengyu Liang , Zhou Sun , Liangchen Xie , Ruoxuan Sun , Na Zhao , LiZeng Peng , Xiaojun Yao","doi":"10.1002/ajoc.70268","DOIUrl":"10.1002/ajoc.70268","url":null,"abstract":"<div><div>A BF<sub>3</sub>·Et<sub>2</sub>O‐promoted cascade annulation of 2‐propynolphenols is described for the synthesis of 2‐substituted 3‐sulfenylbenzofurans. This protocol was achieved through a sequential Meyer–Schuster rearrangement/nucleophilic addition/intramolecular annulation sequence. Mechanistic studies and density functional theory (DFT) calculations provided robust support for the proposed reaction pathway and identified the combined process of the ring‐closing step and the hydrogen transfer process as the rate‐determining step. This method provides an efficient route to C─S bond formation for the assembly of a wide range of 3‐sulfenylbenzofurans in excellent yields under mild conditions. The screening of these 3‐sulfenylbenzofurans against four human cancer cell lines indicated their excellent anticancer activities, wherein compound <strong>3y</strong> strongly inhibited prostate cancer cells, with a half‐maximal inhibitory concentration value of 7.24 ± 0.45 µM.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"15 1","pages":"Article e70268"},"PeriodicalIF":2.7,"publicationDate":"2026-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145891155","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}
Isoquinolin‐1(2H)‐ones represent an important class of nitrogen‐containing heterocycles widely found in natural products and pharmacologically active compounds. Recent developments in their functionalization have enabled the construction of structurally diverse and bioactive derivatives through selective halogenation and C–X (X = S, N) bond formation. This review summarizes key methodologies, including transition‐metal‐catalyzed processes and metal‐free radical‐based approaches. Adopting sustainable techniques such as visible‐light photocatalysis, electrochemical methods, and solvent‐free protocols has significantly improved the environmental profile of these transformations. These advances offer versatile and efficient tools for synthesizing functionally rich isoquinolone derivatives with broad relevance in medicinal chemistry and materials science.
{"title":"Synthetic Diversification of Isoquinolin‐1(2H)‐Ones: Emerging Strategies and Methodological Advances","authors":"Ritika Sharma , Inder Kumar , Manisha , Upendra Sharma","doi":"10.1002/ajoc.70279","DOIUrl":"10.1002/ajoc.70279","url":null,"abstract":"<div><div>Isoquinolin‐1(2<em>H</em>)‐ones represent an important class of nitrogen‐containing heterocycles widely found in natural products and pharmacologically active compounds. Recent developments in their functionalization have enabled the construction of structurally diverse and bioactive derivatives through selective halogenation and C–X (X = S, N) bond formation. This review summarizes key methodologies, including transition‐metal‐catalyzed processes and metal‐free radical‐based approaches. Adopting sustainable techniques such as visible‐light photocatalysis, electrochemical methods, and solvent‐free protocols has significantly improved the environmental profile of these transformations. These advances offer versatile and efficient tools for synthesizing functionally rich isoquinolone derivatives with broad relevance in medicinal chemistry and materials science.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"15 1","pages":"Article e70279"},"PeriodicalIF":2.7,"publicationDate":"2026-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145887781","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}
Dong Zhang , Yuting Gao , Xiaojun Xu , Chunjie Ni , Qingdong Wang , Jin Wang
In this paper, we have developed an efficient and simple method for obtaining difluoromethylated benzothiophene derivatives under electrochemical conditions. The method utilizes 2‐alkynylthioanisoles, which contain active alkynes as substrates, affordable sodium difluoromethanesulfinate (HCF2SO2Na) as the fluorinating reagent. By the anodic oxidation to excite difluoromethyl radicals under electrochemical conditions and triggering difunctionalization reactions through the addition of alkynes via free radicals to form target products. It features excellent functional group compatibility and affords a variety of benzothiophene derivatives in good yields.
{"title":"Efficient Synthesis of Difluoromethylated Benzothiophene Derivatives Under Electrochemical Conditions","authors":"Dong Zhang , Yuting Gao , Xiaojun Xu , Chunjie Ni , Qingdong Wang , Jin Wang","doi":"10.1002/ajoc.70280","DOIUrl":"10.1002/ajoc.70280","url":null,"abstract":"<div><div>In this paper, we have developed an efficient and simple method for obtaining difluoromethylated benzothiophene derivatives under electrochemical conditions. The method utilizes 2‐alkynylthioanisoles, which contain active alkynes as substrates, affordable sodium difluoromethanesulfinate (HCF<sub>2</sub>SO<sub>2</sub>Na) as the fluorinating reagent. By the anodic oxidation to excite difluoromethyl radicals under electrochemical conditions and triggering difunctionalization reactions through the addition of alkynes via free radicals to form target products. It features excellent functional group compatibility and affords a variety of benzothiophene derivatives in good yields.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"15 1","pages":"Article e70280"},"PeriodicalIF":2.7,"publicationDate":"2026-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145887302","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}
Xuan Liu , Yujie Zou , Puying Luo , Yan Hong , Liu Yang , Qiuping Ding
A cascade alkylation/cyclization reaction of ortho‐isocyanodiaryl amines with 1,3‐dicarbonyl compounds in the presence of Mn(OAc)3·2H2O has been developed. This reaction offers an efficient protocol to alkylated dibenzodiazepines, and features simple and mild conditions, wide substrate scope, and good functional group tolerance. All of those examined products exhibited obvious cytotoxic activities against Hela, HepG‐2, SGC‐7901, and HL‐60 cells at 20 µM. Compounds 3f, 3i, and 3r show better activity than 5‐FU on SGC‐7901 cells.
{"title":"Cascade Alkylation/Cyclization of ortho‐Isocyanodiaryl Amines to Alkylated Dibenzodiazepines and Their Primary Activities","authors":"Xuan Liu , Yujie Zou , Puying Luo , Yan Hong , Liu Yang , Qiuping Ding","doi":"10.1002/ajoc.202500634","DOIUrl":"10.1002/ajoc.202500634","url":null,"abstract":"<div><div>A cascade alkylation/cyclization reaction of <em>ortho</em>‐isocyanodiaryl amines with 1,3‐dicarbonyl compounds in the presence of Mn(OAc)<sub>3</sub>·2H<sub>2</sub>O has been developed. This reaction offers an efficient protocol to alkylated dibenzodiazepines, and features simple and mild conditions, wide substrate scope, and good functional group tolerance. All of those examined products exhibited obvious cytotoxic activities against Hela, HepG‐2, SGC‐7901, and HL‐60 cells at 20 µM. Compounds <strong>3f</strong>, <strong>3i</strong>, and <strong>3r</strong> show better activity than 5‐FU on SGC‐7901 cells.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"15 1","pages":"Article e00634"},"PeriodicalIF":2.7,"publicationDate":"2026-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145887278","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}
Chiral liquid crystal (LC) materials are indispensable functional components of advanced optoelectronic devices. In this study, we fabricated chiral nematic liquid crystal (N*‐LC) devices by introducing perylene and its N,N‐di‐n‐octyl‐3,4,9,10‐perylenetetracarboxylic diimide (OPDI) derivative, as achiral luminophores, into an N*‐LC host composed of the achiral 4'‐pentyl‐4‐cyanobiphenyl (5CB) LC and the planar‐chiral 4,12‐dihydroxy[2.2]paracyclophane ([2.2]‐PCP) dopant. Remarkably, both perylene and OPDI exhibited pronounced circularly polarized luminescence (CPL) within the planar‐chiral‐dopant‐induced N*‐LC environment, despite the use of achiral luminophores. Furthermore, the handedness of the CPL can be controlled by the planar chirality of the [2.2]‐PCP dopant. In addition, the resulting N*‐LC materials exhibited rapid and reversible inversion of CPL handedness when a direct‐current (DC) electric field was applied and then removed. This reversible behavior is ascribable to the electric‐field‐induced phase transition between the helical N*‐LC structure of 5CB and another ordered phase. These findings provide a new material design principle in which a planar‐chiral dopant induces the N*‐LC phase in 5CB, thereby enabling high‐speed, reversible CPL modulation based on the application of an electric field.
{"title":"Fast and Reversible Circularly Polarized Luminescence Switching in Planar Chirality‐Induced Chiral Nematic Liquid Crystals in a DC Electric Field","authors":"Honoka Akiyama , Kosuke Kaneko , Shinichi Naya , Yoshitane Imai","doi":"10.1002/ajoc.70303","DOIUrl":"10.1002/ajoc.70303","url":null,"abstract":"<div><div>Chiral liquid crystal (LC) materials are indispensable functional components of advanced optoelectronic devices. In this study, we fabricated chiral nematic liquid crystal (N*‐LC) devices by introducing perylene and its <em>N,N</em>‐di‐<em>n</em>‐octyl‐3,4,9,10‐perylenetetracarboxylic diimide (OPDI) derivative, as achiral luminophores, into an N*‐LC host composed of the achiral 4'‐pentyl‐4‐cyanobiphenyl (5CB) LC and the planar‐chiral 4,12‐dihydroxy[2.2]paracyclophane ([2.2]‐PCP) dopant. Remarkably, both perylene and OPDI exhibited pronounced circularly polarized luminescence (CPL) within the planar‐chiral‐dopant‐induced N*‐LC environment, despite the use of achiral luminophores. Furthermore, the handedness of the CPL can be controlled by the planar chirality of the [2.2]‐PCP dopant. In addition, the resulting N*‐LC materials exhibited rapid and reversible inversion of CPL handedness when a direct‐current (DC) electric field was applied and then removed. This reversible behavior is ascribable to the electric‐field‐induced phase transition between the helical N*‐LC structure of 5CB and another ordered phase. These findings provide a new material design principle in which a planar‐chiral dopant induces the N*‐LC phase in 5CB, thereby enabling high‐speed, reversible CPL modulation based on the application of an electric field.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"15 1","pages":"Article e70303"},"PeriodicalIF":2.7,"publicationDate":"2026-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146057935","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}
Andrey I. Puzanov , Dmitriy N. Zakusilo , Elena V. Ipatova , Aleksander V. Vasilyev
This mini review describes recent achievements in the production and chemical transformations of muconic acid (hexa‐2,4‐dienedioic acid, HO2CCH═CHCH═CHCO2H). Muconic acid may be obtained from renewable lignocellulosic materials, and it is considered as a bio‐based platform molecule. This acid has a great practical value due to its hydrogenation into adipic acid, which is used for nylon production. Muconic acid and its derivatives take part in many important and useful synthetic transformations such as Diels‐Alder reactions, isomerization, lactonization, polymerization, polycondensation, and others. However, up to the moment, muconic acid is not yet widely used in the fine organic synthesis. This review is focused on preparation, reactions, and on some novel applications of muconic acid and its derivatives in organic synthesis. The aim of this review is to attract attention to muconic acid, which has a high potential to be a valuable precursor for preparation of novel compounds and materials.
{"title":"Muconic Acid: An Underexplored Building Block for Fine Organic Synthesis","authors":"Andrey I. Puzanov , Dmitriy N. Zakusilo , Elena V. Ipatova , Aleksander V. Vasilyev","doi":"10.1002/ajoc.70286","DOIUrl":"10.1002/ajoc.70286","url":null,"abstract":"<div><div>This mini review describes recent achievements in the production and chemical transformations of muconic acid (hexa‐2,4‐dienedioic acid, HO<sub>2</sub>CCH═CHCH═CHCO<sub>2</sub>H). Muconic acid may be obtained from renewable lignocellulosic materials, and it is considered as a bio‐based platform molecule. This acid has a great practical value due to its hydrogenation into adipic acid, which is used for nylon production. Muconic acid and its derivatives take part in many important and useful synthetic transformations such as Diels‐Alder reactions, isomerization, lactonization, polymerization, polycondensation, and others. However, up to the moment, muconic acid is not yet widely used in the fine organic synthesis. This review is focused on preparation, reactions, and on some novel applications of muconic acid and its derivatives in organic synthesis. The aim of this review is to attract attention to muconic acid, which has a high potential to be a valuable precursor for preparation of novel compounds and materials.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"15 1","pages":"Article e70286"},"PeriodicalIF":2.7,"publicationDate":"2026-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145887312","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}
Dr. Qui‐Hien Nguyen , Minh‐Thuan Nguyen , Uyen‐Vi V. Nguyen , Quang‐Vinh Phan , Ngan‐Ha T. Do , Dieu‐Huong T. Pham , Bang‐Vu Duong , Dr. Tin V. T. Nguyen
Photochemical strategies enable sustainable C─H bond activation under mild conditions via hydrogen atom transfer (HAT). Nitrogen‐centered radicals, particularly from N‐fluorobenzenesulfonimide (NFSI), are effective HAT agents, but typically require complex catalytic systems. Here, we report a photo‐mediated protocol for aerobic oxidation of benzylic C(sp3)─H bonds using NFSI or Selectfluor without the need for metal‐ or photo‐catalyst. This method enables the direct synthesis of ketones and carboxylic acids from aryl alkanes under ambient conditions without directing groups. The same conditions also allow for alcohol oxidation and benzylic ether deprotection to phenol, demonstrating broad synthetic utility. This operationally simple strategy offers a sustainable alternative for late‐stage oxidation in organic synthesis.
{"title":"Photo‐Mediated Aerobic Oxidation of Benzylic C–H Bonds and Alcohols by N‐Center Radical","authors":"Dr. Qui‐Hien Nguyen , Minh‐Thuan Nguyen , Uyen‐Vi V. Nguyen , Quang‐Vinh Phan , Ngan‐Ha T. Do , Dieu‐Huong T. Pham , Bang‐Vu Duong , Dr. Tin V. T. Nguyen","doi":"10.1002/ajoc.202500583","DOIUrl":"10.1002/ajoc.202500583","url":null,"abstract":"<div><div>Photochemical strategies enable sustainable C─H bond activation under mild conditions <em>via</em> hydrogen atom transfer (HAT). Nitrogen‐centered radicals, particularly from <em>N</em>‐fluorobenzenesulfonimide (NFSI), are effective HAT agents, but typically require complex catalytic systems. Here, we report a photo‐mediated protocol for aerobic oxidation of benzylic C(<em>sp<sup>3</sup></em>)─H bonds using NFSI or Selectfluor without the need for metal‐ or photo‐catalyst. This method enables the direct synthesis of ketones and carboxylic acids from aryl alkanes under ambient conditions without directing groups. The same conditions also allow for alcohol oxidation and benzylic ether deprotection to phenol, demonstrating broad synthetic utility. This operationally simple strategy offers a sustainable alternative for late‐stage oxidation in organic synthesis.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"15 1","pages":"Article e00583"},"PeriodicalIF":2.7,"publicationDate":"2026-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145887243","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}
Sabera Sultana , Khurshid Ahmad , Yong Rok Lee , Anil K. Saikia
We developed a regioselective one‐pot strategy for synthesizing highly substituted arylated 1H‐indenes bearing heterocycles using BF3·OEt2‐catalyzed multicomponent reactions. The proposed reaction mechanism includes BF3 complex formation, tautomerization, nucleophilic aryl addition to arylalkyne, cyclization via a 4π‐Nazarov‐type intermediate, and deprotonation. The anticancer potential of the resulting compounds was evaluated using molecular docking studies that targeted the epidermal growth factor receptor (EGFR). All synthesized indene derivatives had high binding affinities, surpassing those of the reference drug erlotinib, indicating their potential as EGFR inhibitors. These findings suggest that, with further biological validation, the newly synthesized arylated indenes could serve as effective leads for the development of anticancer drugs.
{"title":"BF3.OEt2‐Catalyzed Regioselective One‐Pot Multicomponent Synthesis of Arylated 1H‐Indenes With EGFR Inhibitory Potential: A Combined Synthetic and Biocomputational Study","authors":"Sabera Sultana , Khurshid Ahmad , Yong Rok Lee , Anil K. Saikia","doi":"10.1002/ajoc.70264","DOIUrl":"10.1002/ajoc.70264","url":null,"abstract":"<div><div>We developed a regioselective one‐pot strategy for synthesizing highly substituted arylated 1<em>H</em>‐indenes bearing heterocycles using BF<sub>3</sub>·OEt<sub>2</sub>‐catalyzed multicomponent reactions. The proposed reaction mechanism includes BF<sub>3</sub> complex formation, tautomerization, nucleophilic aryl addition to arylalkyne, cyclization via a 4π‐Nazarov‐type intermediate, and deprotonation. The anticancer potential of the resulting compounds was evaluated using molecular docking studies that targeted the epidermal growth factor receptor (EGFR). All synthesized indene derivatives had high binding affinities, surpassing those of the reference drug erlotinib, indicating their potential as EGFR inhibitors. These findings suggest that, with further biological validation, the newly synthesized arylated indenes could serve as effective leads for the development of anticancer drugs.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"15 1","pages":"Article e70264"},"PeriodicalIF":2.7,"publicationDate":"2026-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145887233","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}
Amol S. Dehade , Vir Bahadur , Niriksha S. Pai Kane , Prashantha Kamath , Gopal Kurhe , Partha P. Mukhopadhyay
The mechanochemical synthesis of amides via direct ester amidation through ball milling represents a significant advancement in sustainable organic synthesis. This methodology exploits the in situ generation of isopropylmagnesium bromide within the mechanochemical environment to activate ester substrates toward nucleophilic attack by amines, effectively implementing the historically underutilized Bodroux reaction under mild, solvent‐minimized conditions. Mechanochemical activation overcomes traditional limitations of organomagnesium chemistry by eliminating moisture sensitivity concerns and enabling efficient mixing of heterogeneous reaction components. The method demonstrates remarkable versatility, accommodating a diverse range of substrates, including heteroaromatic, heterocyclic, and aliphatic components. Notably, substrates bearing sensitive functional groups perform exceptionally well under these mechanochemical conditions. Successful gram‐scale synthesis of pharmaceutical and agrochemical targets validates the practical utility and scalability of this approach, positioning mechanochemical amidation as a viable alternative to traditional coupling reagent‐based methodologies.
{"title":"Mechanochemical Bodroux Reaction: Sustainable Ball Milling Approach for Direct Amidation of Esters","authors":"Amol S. Dehade , Vir Bahadur , Niriksha S. Pai Kane , Prashantha Kamath , Gopal Kurhe , Partha P. Mukhopadhyay","doi":"10.1002/ajoc.202500629","DOIUrl":"10.1002/ajoc.202500629","url":null,"abstract":"<div><div>The mechanochemical synthesis of amides <em>via</em> direct ester amidation through ball milling represents a significant advancement in sustainable organic synthesis. This methodology exploits the in situ generation of isopropylmagnesium bromide within the mechanochemical environment to activate ester substrates toward nucleophilic attack by amines, effectively implementing the historically underutilized Bodroux reaction under mild, solvent‐minimized conditions. Mechanochemical activation overcomes traditional limitations of organomagnesium chemistry by eliminating moisture sensitivity concerns and enabling efficient mixing of heterogeneous reaction components. The method demonstrates remarkable versatility, accommodating a diverse range of substrates, including heteroaromatic, heterocyclic, and aliphatic components. Notably, substrates bearing sensitive functional groups perform exceptionally well under these mechanochemical conditions. Successful gram‐scale synthesis of pharmaceutical and agrochemical targets validates the practical utility and scalability of this approach, positioning mechanochemical amidation as a viable alternative to traditional coupling reagent‐based methodologies.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"15 1","pages":"Article e00629"},"PeriodicalIF":2.7,"publicationDate":"2026-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145887510","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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