Isabella F. S. Marra, Larissa P. Silva, Pedro P. De Castro, Leonã S. Flores, Kleber T. De Oliveira, Paulo E. N. De Souza, Brenno A. D. Neto, Hélio F. Dos Santos, Giovanni Wilson Amarante
Visible-light-driven dual catalysis was employed to stereoselectively produce densely substituted cyclobutanes from Erlenmeyer-Plöchl azlactones. The single-step preparation of non-natural amino acid dimers containing the cyclobutane moiety was achieved through a synergy between iridium photocatalysis and catalytic nickel(II) triflate as a Lewis acid. The desired 1,2-(zeta)-Z,E-isomers were isolated in good yields and with high regio- and diastereoselectivity (in all cases, >19:1 d.r.). To the best of our knowledge, this is the first report of direct access to truxinic acid analogues using azlactones. Control experiments, EPR reaction monitoring, and DFT calculations suggest that the presence of a Lewis acid, combined with the use of powerful blue LEDs, plays a crucial role in the reactivity of this reaction.
{"title":"Visible-Light-Enabled Dual-Catalysis Approach to Stereoselective [2 + 2] Cycloaddition of Erlenmeyer-Plöchl Azlactones","authors":"Isabella F. S. Marra, Larissa P. Silva, Pedro P. De Castro, Leonã S. Flores, Kleber T. De Oliveira, Paulo E. N. De Souza, Brenno A. D. Neto, Hélio F. Dos Santos, Giovanni Wilson Amarante","doi":"10.1002/ajoc.202400271","DOIUrl":"https://doi.org/10.1002/ajoc.202400271","url":null,"abstract":"Visible-light-driven dual catalysis was employed to stereoselectively produce densely substituted cyclobutanes from Erlenmeyer-Plöchl azlactones. The single-step preparation of non-natural amino acid dimers containing the cyclobutane moiety was achieved through a synergy between iridium photocatalysis and catalytic nickel(II) triflate as a Lewis acid. The desired 1,2-(zeta)-Z,E-isomers were isolated in good yields and with high regio- and diastereoselectivity (in all cases, >19:1 d.r.). To the best of our knowledge, this is the first report of direct access to truxinic acid analogues using azlactones. Control experiments, EPR reaction monitoring, and DFT calculations suggest that the presence of a Lewis acid, combined with the use of powerful blue LEDs, plays a crucial role in the reactivity of this reaction.","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.7,"publicationDate":"2024-08-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142217024","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}
Jabir Khan, Rina Mahato, Kanhaiya Kanhaiya, Chinmoy Kumar Hazra
A metal‐free one‐pot synthesis route has been documented for the production of 1,1‐unsymmetrical diaryl alkanes via reductive Friedel−Crafts alkylation of arenes with carbonyl compounds in 1,1,1,3,3,3,‐hexafluoroisopropanol (HFIP) solvent. This approach exhibits a wide substrate scope accommodating diverse functionalities. The transformation of carbonyl compounds into alkylated products is facilitated by dimethylchlorosilane (Me2SiClH) reduction, succeeded via nucleophilic attack of arenes. The established protocol demonstrates a promising strategy for converting indoline‐2,3‐dione into α‐aryl oxindoles with high yields. The reaction involves reduction with Me2SiClH, followed by the attack of arenes in the presence of TfOH catalyst. The devised protocol offers scalability and remarkable tolerance towards various functional groups. Control experiments provide insights into the reaction mechanism, indicating an ionic pathway and highlighting the crucial roles of HFIP and Me2SiClH. Furthermore, the method is adaptable for late‐stage functionalization of numerous natural products and pharmaceuticals such as Sesamol, Thymol, Paracetamol, Menthol, and Nerol. Significantly, the technique has proven effective in the efficient synthesis of the anticoagulant drug Phenprocoumon and the rodent control agent Coumatetralyl.
{"title":"Silane‐Mediated Alkylation of Arenes via Reductive Friedel‐Crafts Reaction Using Carbonyl Compounds","authors":"Jabir Khan, Rina Mahato, Kanhaiya Kanhaiya, Chinmoy Kumar Hazra","doi":"10.1002/ajoc.202400347","DOIUrl":"https://doi.org/10.1002/ajoc.202400347","url":null,"abstract":"A metal‐free one‐pot synthesis route has been documented for the production of 1,1‐unsymmetrical diaryl alkanes via reductive Friedel−Crafts alkylation of arenes with carbonyl compounds in 1,1,1,3,3,3,‐hexafluoroisopropanol (HFIP) solvent. This approach exhibits a wide substrate scope accommodating diverse functionalities. The transformation of carbonyl compounds into alkylated products is facilitated by dimethylchlorosilane (Me2SiClH) reduction, succeeded via nucleophilic attack of arenes. The established protocol demonstrates a promising strategy for converting indoline‐2,3‐dione into α‐aryl oxindoles with high yields. The reaction involves reduction with Me2SiClH, followed by the attack of arenes in the presence of TfOH catalyst. The devised protocol offers scalability and remarkable tolerance towards various functional groups. Control experiments provide insights into the reaction mechanism, indicating an ionic pathway and highlighting the crucial roles of HFIP and Me2SiClH. Furthermore, the method is adaptable for late‐stage functionalization of numerous natural products and pharmaceuticals such as Sesamol, Thymol, Paracetamol, Menthol, and Nerol. Significantly, the technique has proven effective in the efficient synthesis of the anticoagulant drug Phenprocoumon and the rodent control agent Coumatetralyl.","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.7,"publicationDate":"2024-08-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142217025","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}
Arisu Koyanagi, Dr. Yuki Murata, Dr. Mio Matsumura, Prof. Dr. Shuji Yasuike
The cover design showcases a general method for the synthesis of sulfenamides from various benzoazole-2-thiones with amines using bismuth reagent. The brother′s azole-thiones and the sister′s amines being reacted with the bismuth reagent to produce the sulfenamide that blooms beautifully like fireworks. In the night sky, the S-N bond formation is depicted to resemble the Milky Way. The reactions of benzoazole-2-thiones with various primary or secondary amines in the presence of triphenylbismuth dichloride (Ph3BiCl2) at 60 °C in DMSO under aerobic conditions afforded the corresponding sulfenamides in moderate-to-excellent yields. This reaction is the first example of an efficient S–N bond formation reaction utilizing a lowtoxicity pentavalent organobismuth reagent under mild reaction conditions. The reaction will likely be applied to develop compounds with medicinal value or industrial utility. More information can be found in article number e202400138 by Yuki Murata, Shuji Yasuike, and co-workers.
{"title":"Front Cover: Synthesis of Sulfenamides from Benzoazole-2-thiones with Primary and Secondary Amines using Triphenylbismuth Dichloride-Mediated S−N Bond Formation Reaction (Asian J. Org. Chem. 8/2024)","authors":"Arisu Koyanagi, Dr. Yuki Murata, Dr. Mio Matsumura, Prof. Dr. Shuji Yasuike","doi":"10.1002/ajoc.202480801","DOIUrl":"https://doi.org/10.1002/ajoc.202480801","url":null,"abstract":"<p>The cover design showcases a general method for the synthesis of sulfenamides from various benzoazole-2-thiones with amines using bismuth reagent. The brother′s azole-thiones and the sister′s amines being reacted with the bismuth reagent to produce the sulfenamide that blooms beautifully like fireworks. In the night sky, the S-N bond formation is depicted to resemble the Milky Way. The reactions of benzoazole-2-thiones with various primary or secondary amines in the presence of triphenylbismuth dichloride (Ph3BiCl2) at 60 °C in DMSO under aerobic conditions afforded the corresponding sulfenamides in moderate-to-excellent yields. This reaction is the first example of an efficient S–N bond formation reaction utilizing a lowtoxicity pentavalent organobismuth reagent under mild reaction conditions. The reaction will likely be applied to develop compounds with medicinal value or industrial utility. More information can be found in article number e202400138 by Yuki Murata, Shuji Yasuike, and co-workers.<figure>\u0000 <div><picture>\u0000 <source></source></picture><p></p>\u0000 </div>\u0000 </figure>\u0000 </p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.8,"publicationDate":"2024-08-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ajoc.202480801","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141980209","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}
Sumit Kumar, Aditi Arora, Shivani Sapra, Riya Chaudhary, Brajendra Kumar Singh, Sunil K. Singh
Over the past three decades, triflate salts have emerged as crucial Lewis acid catalysts in organic synthesis, playing a significant role in cyclization, C‐H bond functionalization, and various other reactions. Among these, rare‐earth triflates have garnered attention due to their water compatibility, environmental friendliness, noncorrosive nature, and reusability. In particular, scandium(III) triflate [Sc(OTf)3] stands out as a water‐resistant Lewis acid with remarkable catalytic activity in aqueous environments. Unlike typical Lewis acids such as AlCl3, BF3, and SnCl4, which are decomposed or deactivated by water, Sc(OTf)3 remains stable and effective. Its exceptional Lewis acidity, resilience against hydrolysis, and recyclability make it a prominent green catalyst. The unique stability of Sc(OTf)3 in water is attributed to the smaller size of scandium ions (Sc3+), enhancing its catalytic efficiency. Sc(OTf)3 has a longstanding history in organic synthesis, facilitating a wide range of reactions including aldol, Michael, allylation, Friedel‐Crafts acylations, Diels‐Alder, Mannich, cycloadditions (including cyclopropanation), and cascade reactions. The increasing utilization of Sc(OTf)3 over the past decade underscores the necessity for updated insights. This review provides a concise overview of the versatility of Sc(OTf)3 as a catalyst, focusing on developments from 2017 to 2024.
{"title":"Recent Advances in Scandium(III) Triflate Catalysis: A Review","authors":"Sumit Kumar, Aditi Arora, Shivani Sapra, Riya Chaudhary, Brajendra Kumar Singh, Sunil K. Singh","doi":"10.1002/ajoc.202400295","DOIUrl":"https://doi.org/10.1002/ajoc.202400295","url":null,"abstract":"Over the past three decades, triflate salts have emerged as crucial Lewis acid catalysts in organic synthesis, playing a significant role in cyclization, C‐H bond functionalization, and various other reactions. Among these, rare‐earth triflates have garnered attention due to their water compatibility, environmental friendliness, noncorrosive nature, and reusability. In particular, scandium(III) triflate [Sc(OTf)3] stands out as a water‐resistant Lewis acid with remarkable catalytic activity in aqueous environments. Unlike typical Lewis acids such as AlCl3, BF3, and SnCl4, which are decomposed or deactivated by water, Sc(OTf)3 remains stable and effective. Its exceptional Lewis acidity, resilience against hydrolysis, and recyclability make it a prominent green catalyst. The unique stability of Sc(OTf)3 in water is attributed to the smaller size of scandium ions (Sc3+), enhancing its catalytic efficiency. Sc(OTf)3 has a longstanding history in organic synthesis, facilitating a wide range of reactions including aldol, Michael, allylation, Friedel‐Crafts acylations, Diels‐Alder, Mannich, cycloadditions (including cyclopropanation), and cascade reactions. The increasing utilization of Sc(OTf)3 over the past decade underscores the necessity for updated insights. This review provides a concise overview of the versatility of Sc(OTf)3 as a catalyst, focusing on developments from 2017 to 2024.","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.7,"publicationDate":"2024-08-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142216916","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}
Zhou Zhang, Siyu Shi, Hai Guo, Zhiqiang Shen, Xia Liu, Jinqi Huang, Wenjin Yan
A photoinduced Wolff rearrangement/chiral isothiourea catalyzed [4+2] cycloaddition reaction of pyrazolone derivatives and α‐diazoketones was developed, affording the corresponding dihydropyrano[2,3‐c]pyrazolone derivatives in moderate to good yields (50‐94%) with satisfactory to excellent diastereoselectivities (> 20:1 dr, in almost all cases) and enantioselectivities of 31‐99%. This protocol features readily available substrates, mild reaction conditions, and effective construction of vicinal tertiary and quaternary carbon stereocenters.
{"title":"Construction of dihydropyrano[2,3‐c]pyrazolone via photoinduced Wolff rearrangement/chiral isothiourea catalyzed [4+2] cyclization reaction","authors":"Zhou Zhang, Siyu Shi, Hai Guo, Zhiqiang Shen, Xia Liu, Jinqi Huang, Wenjin Yan","doi":"10.1002/ajoc.202400387","DOIUrl":"https://doi.org/10.1002/ajoc.202400387","url":null,"abstract":"A photoinduced Wolff rearrangement/chiral isothiourea catalyzed [4+2] cycloaddition reaction of pyrazolone derivatives and α‐diazoketones was developed, affording the corresponding dihydropyrano[2,3‐c]pyrazolone derivatives in moderate to good yields (50‐94%) with satisfactory to excellent diastereoselectivities (> 20:1 dr, in almost all cases) and enantioselectivities of 31‐99%. This protocol features readily available substrates, mild reaction conditions, and effective construction of vicinal tertiary and quaternary carbon stereocenters.","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.7,"publicationDate":"2024-08-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142216921","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}
Abhishek Kumar, Arvind Kumar Jaiswal, Ajay Kishor Kushawaha, Anushka Singh, Ruchir Kant, Sanjeev K. Shukla, Koneni V. Sashidhara
: Herein, we have developed a metal-free, atom-economical, intrinsically sustainable approach for synthesizing unprotected 4,5-diamino pyrazoles from readily available 1,2-diaza-1,3-dienes. This approach utilizes inexpensive hydrazine hydrate as the aminating source. Further, we have explored the reactivity of 4,5-diamino pyrazole to synthesize fused pyrazolo[3,4-d]-1,2,3-triazole heterocyclic compounds. We have also successfully demonstrated the synthetic utility of this methodology in synthesizing two drug analogs: analgesic difenamizole and anti-psychotic CDPPB. The role of the phenyl ring of 3-substituted-1,2-diaza-1,3-diene was explained with the help of control experimental and density functional theory (DFT) computation studies.
{"title":"A Metal-Free Amination of 1,2-Diaza-1,3-dienes Using Hydrazine Hydrate Through N-N Bond Cleavage","authors":"Abhishek Kumar, Arvind Kumar Jaiswal, Ajay Kishor Kushawaha, Anushka Singh, Ruchir Kant, Sanjeev K. Shukla, Koneni V. Sashidhara","doi":"10.1002/ajoc.202400169","DOIUrl":"https://doi.org/10.1002/ajoc.202400169","url":null,"abstract":": Herein, we have developed a metal-free, atom-economical, intrinsically sustainable approach for synthesizing unprotected 4,5-diamino pyrazoles from readily available 1,2-diaza-1,3-dienes. This approach utilizes inexpensive hydrazine hydrate as the aminating source. Further, we have explored the reactivity of 4,5-diamino pyrazole to synthesize fused pyrazolo[3,4-d]-1,2,3-triazole heterocyclic compounds. We have also successfully demonstrated the synthetic utility of this methodology in synthesizing two drug analogs: analgesic difenamizole and anti-psychotic CDPPB. The role of the phenyl ring of 3-substituted-1,2-diaza-1,3-diene was explained with the help of control experimental and density functional theory (DFT) computation studies.","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.7,"publicationDate":"2024-08-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142216919","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}
Dandamudi Lenin, Dharti Mistry, Nikunjna Benjamin Makwana, Payal Malvi
: A simple synthesis of 3‐hydroxy‐2‐(2‐nitro‐1‐arylethyl)cyclohex‐2‐en‐1‐ones, 3‐hydroxy‐5,5‐dimethyl‐2‐(2‐nitro‐1‐arylethyl)cyclohex‐2‐en‐1‐ones and 4‐hydroxy‐3‐(2‐nitro‐1‐arylethyl)pent‐3‐en‐2‐onesvia conjugate addition of cyclic 1,3‐diketones, 1,3‐cyclohexanedione and 5,5‐dimethyl‐1,3‐cyclohexanedione and acyclic 1,3‐diketone, pentane‐2,4‐dione to β‐nitrostyrenes were reported. This methodology is pleasing with reliability and scalability with gram scale products that can be synthesized
{"title":"A simple and facile conjugate addition of cyclic and acyclic 1,3‐diketones to β‐nitrostyrenes","authors":"Dandamudi Lenin, Dharti Mistry, Nikunjna Benjamin Makwana, Payal Malvi","doi":"10.1002/ajoc.202400355","DOIUrl":"https://doi.org/10.1002/ajoc.202400355","url":null,"abstract":": A simple synthesis of 3‐hydroxy‐2‐(2‐nitro‐1‐arylethyl)cyclohex‐2‐en‐1‐ones, 3‐hydroxy‐5,5‐dimethyl‐2‐(2‐nitro‐1‐arylethyl)cyclohex‐2‐en‐1‐ones and 4‐hydroxy‐3‐(2‐nitro‐1‐arylethyl)pent‐3‐en‐2‐onesvia conjugate addition of cyclic 1,3‐diketones, 1,3‐cyclohexanedione and 5,5‐dimethyl‐1,3‐cyclohexanedione and acyclic 1,3‐diketone, pentane‐2,4‐dione to β‐nitrostyrenes were reported. This methodology is pleasing with reliability and scalability with gram scale products that can be synthesized","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.7,"publicationDate":"2024-08-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142216918","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}
Cyclam is a well‐known example of a polyaza macrocycle. However, there are few reports of its optically active versions. In this study, we synthesized highly symmetric optically active cyclam (S,S,S,S)‐5,7,12,14‐tetraphenyl‐1,4,8,11‐tetraazacyclotetradecane, which has four phenyl groups on the cyclam skeleton, and derivatized it in various ways. We were able to synthesize a chiral Cu complex, an N‐ethyl derivative, and a dithiourea from this optically active cyclam. The structures of the chiral Cu complex and dithiourea were verified by single‐crystal X‐ray diffraction analysis.
Cyclam 是众所周知的多氮杂环大环。然而，有关其光学活性版本的报道却很少。在这项研究中，我们合成了具有高度对称性的光学活性环酰胺 (S,S,S,S,S)-5,7,12,14-四苯基-1,4,8,11-四氮杂环十四烷，其环酰胺骨架上有四个苯基，并通过各种方法对其进行衍生。我们从这种具有光学活性的环戊烷中合成了一种手性 Cu 复合物、一种 N-乙基衍生物和一种二硫脲。单晶 X 射线衍射分析验证了手性铜络合物和二硫脲的结构。
{"title":"Synthesis of Optically Active Cyclam and Its Transformations","authors":"Kazuhiro Yoshida, Yuya Miwa, Yakumo Tojima, Miyuki Takahashi, Daichi Shishido","doi":"10.1002/ajoc.202400310","DOIUrl":"https://doi.org/10.1002/ajoc.202400310","url":null,"abstract":"Cyclam is a well‐known example of a polyaza macrocycle. However, there are few reports of its optically active versions. In this study, we synthesized highly symmetric optically active cyclam (S,S,S,S)‐5,7,12,14‐tetraphenyl‐1,4,8,11‐tetraazacyclotetradecane, which has four phenyl groups on the cyclam skeleton, and derivatized it in various ways. We were able to synthesize a chiral Cu complex, an N‐ethyl derivative, and a dithiourea from this optically active cyclam. The structures of the chiral Cu complex and dithiourea were verified by single‐crystal X‐ray diffraction analysis.","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.7,"publicationDate":"2024-08-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142216917","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}
A simple Ru(II)‐catalyzed protocol for the alkenylation of isoquinolones with readily accessible allyl alcohols to generate aldehyde bearing isoquinolones has been developed. The use of green solvent like dimethyl carbonate makes this method environment‐friendly. Experimental studies were carried out to support the proposed mechanism. The reaction was scaled up to showcase the application of the current method.
{"title":"Ru(II)‐Catalyzed C8 Alkenylation of Isoquinolones with Allyl Alcohol","authors":"Manisha, Tamanna Sharma, Upendra Sharma","doi":"10.1002/ajoc.202400407","DOIUrl":"https://doi.org/10.1002/ajoc.202400407","url":null,"abstract":"A simple Ru(II)‐catalyzed protocol for the alkenylation of isoquinolones with readily accessible allyl alcohols to generate aldehyde bearing isoquinolones has been developed. The use of green solvent like dimethyl carbonate makes this method environment‐friendly. Experimental studies were carried out to support the proposed mechanism. The reaction was scaled up to showcase the application of the current method.","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.8,"publicationDate":"2024-08-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141921434","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}
Heba H. Mohamedy, Eman Fayad, H. Katouah, Hua-Li Qin
An eco‐friendly and efficient method was developed for synthesizing a novel class of aliphatic sulfonyl fluorides in a catalyst‐free one‐pot reaction. The new approach offers a streamlined synthesis for N‐(Substituted)‐2‐(fluorosulfonyl) ethyl carbamodithioates by combining amines, carbon disulfide, with ethenesulfonyl fluoride. The synthesized compounds were obtained in good yields under mild conditions, making this reaction a valuable tool for exploring new chemical transformations.
{"title":"Synthesis of Dithiocarbamate‐Functionalized Aliphatic Sulfonyl Fluoride Via a One‐Pot Three‐Component Reaction","authors":"Heba H. Mohamedy, Eman Fayad, H. Katouah, Hua-Li Qin","doi":"10.1002/ajoc.202400269","DOIUrl":"https://doi.org/10.1002/ajoc.202400269","url":null,"abstract":"An eco‐friendly and efficient method was developed for synthesizing a novel class of aliphatic sulfonyl fluorides in a catalyst‐free one‐pot reaction. The new approach offers a streamlined synthesis for N‐(Substituted)‐2‐(fluorosulfonyl) ethyl carbamodithioates by combining amines, carbon disulfide, with ethenesulfonyl fluoride. The synthesized compounds were obtained in good yields under mild conditions, making this reaction a valuable tool for exploring new chemical transformations.","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.8,"publicationDate":"2024-08-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141929612","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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