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Non-Electronic Activation of Anthracenes Using Steric Repulsion of the 9-Substituent with Chloro Groups at the peri-Positions 利用 9-取代基与周围位置的氯基的立体斥力实现蒽的非电子活化
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2024-08-23 DOI: 10.1002/ajoc.202400381
Annisa Indah Reza, Kento Iwai, Nagatoshi Nishiwaki
{"title":"Non-Electronic Activation of Anthracenes Using Steric Repulsion of the 9-Substituent with Chloro Groups at the peri-Positions","authors":"Annisa Indah Reza,&nbsp;Kento Iwai,&nbsp;Nagatoshi Nishiwaki","doi":"10.1002/ajoc.202400381","DOIUrl":"10.1002/ajoc.202400381","url":null,"abstract":"<p>We investigated how the introduction of substituent at the 9- or 10-position of the 1,8-dichloroanthracene framework affects the horizontal and vertical distortions of the anthracene rings. The 9-substituted anthracenes showed higher distortions than their 10-substituted counterparts due to the steric repulsion with two chloro groups at the <i>peri</i>-positions. The distortion of anthracene framework affected their reactivity. Indeed, 9-substituted anthracenes exhibited higher reactivity to undergo the Diels–Alder reaction with maleic anhydride, which was a result of non-electronic activation.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 11","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-08-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142217022","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Facile Generation of Trideuteromethyl Radical from Alkylsilyl Peroxide and Subsequent Functionalization 从过氧化烷基硅基中简便生成三氚甲基自由基并进行后续功能化处理
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2024-08-22 DOI: 10.1002/ajoc.202400382
Dr. Jiahao Liu, Jiachun Nie, Prof. Dr. Zhe Wang, Prof. Dr. Terumasa Kato, Prof. Dr. Yan Liu, Prof. Dr. Keiji Maruoka
{"title":"Facile Generation of Trideuteromethyl Radical from Alkylsilyl Peroxide and Subsequent Functionalization","authors":"Dr. Jiahao Liu,&nbsp;Jiachun Nie,&nbsp;Prof. Dr. Zhe Wang,&nbsp;Prof. Dr. Terumasa Kato,&nbsp;Prof. Dr. Yan Liu,&nbsp;Prof. Dr. Keiji Maruoka","doi":"10.1002/ajoc.202400382","DOIUrl":"10.1002/ajoc.202400382","url":null,"abstract":"<p>Cu- and Fe- catalyzed trideuteromethylation reactions using alkylsilyl peroxide as trideuteromethyl radical precursor are reported. The alkylsilyl peroxide was synthesized from acetone-d6 in a three-step sequence, and the reactions with various coupling partners afforded efficiently the corresponding N−CD<sub>3</sub>, O−CD<sub>3</sub> and C−CD<sub>3</sub> bond formation products. The radical heptadeuteriopropylation using alkylsilyl peroxide prepared from butyric acid-d7 is also described.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 11","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-08-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142217021","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Synthesis, Anticancer Evaluation, in-silico ADMET and Molecular Docking Studies for Tailored Pyrazolo-Benzothiazole Hybrids 量身定制的吡唑-苯并噻唑混合物的合成、抗癌评估、硅内 ADMET 和分子对接研究
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2024-08-21 DOI: 10.1002/ajoc.202400187
Omkar Bains, Ashish Kumar, Raj Kamal, Rasdeep Kour, Simrandeep Kaur, Satwinderjeet Kaur, Raman Jangra, Purshotam Sharma, Ravinder Kumar
{"title":"Synthesis, Anticancer Evaluation, in-silico ADMET and Molecular Docking Studies for Tailored Pyrazolo-Benzothiazole Hybrids","authors":"Omkar Bains,&nbsp;Ashish Kumar,&nbsp;Raj Kamal,&nbsp;Rasdeep Kour,&nbsp;Simrandeep Kaur,&nbsp;Satwinderjeet Kaur,&nbsp;Raman Jangra,&nbsp;Purshotam Sharma,&nbsp;Ravinder Kumar","doi":"10.1002/ajoc.202400187","DOIUrl":"10.1002/ajoc.202400187","url":null,"abstract":"<p>The present article demonstrates the regioselective synthesis, characterization, and biological evaluation of eighteen novel pyrazolo-benzothiazole hybrid molecules 5a–5r. We have utilized β,β-ditosyloxy ketone protocol to synthesize these hybrid molecules. The synthesized compounds were tested for their <i>in-vitro</i> antiproliferative activities using MTT assay against breast cancer (MCF-7), cervical cancer (HeLa), and Lung cancer (A549) cell lines. Hybrid molecules 5a, 5m, 5n, and 5o with IC<sub>50</sub> values of 0.359 mM, 0.051 mM, 0.079 mM, and 0.259 mM respectively exhibited admirable growth inhibitory properties against MCF-7 cancer cells which are even better than reference carboplatin drug having IC<sub>50</sub> (0.439 mM). Compound 5k with IC<sub>50</sub> value of 0.765 mM was found to be the most potent antiproliferative agent for the HeLa cancer cells. Moreover, hybrid molecule 5f with IC<sub>50</sub> value of 0.706 mM exhibited better inhibitory activity against A549 cancer cells in comparison to the reference carboplatin drug having IC<sub>50</sub> (0.805 mM). The mechanism of cellular toxicity was studied using the Annexin V-FITC/PI double staining method and cell cycle assay. Molecular docking studies for all the synthesized compounds have also been performed in the binding pocket of VEGFR2 sites (PDB code: 4ASD). Finally, the ADMET profile of the potent molecules was investigated to predict their drug-likeness behaviour.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 11","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-08-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142217023","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Ionic Liquid-Functionalized Porous Materials for Catalyzing CO2 Cycloaddition Reaction 用于催化二氧化碳环化反应的离子液体功能化多孔材料
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2024-08-20 DOI: 10.1002/ajoc.202400316
Kaizhi Xv, Jiawen Yang, Xuejun Li, Ying Liang, Yingming Pan
{"title":"Ionic Liquid-Functionalized Porous Materials for Catalyzing CO2 Cycloaddition Reaction","authors":"Kaizhi Xv,&nbsp;Jiawen Yang,&nbsp;Xuejun Li,&nbsp;Ying Liang,&nbsp;Yingming Pan","doi":"10.1002/ajoc.202400316","DOIUrl":"10.1002/ajoc.202400316","url":null,"abstract":"<p>Ionic liquids (ILs) are incorporated into traditional porous materials to create ILs-functionalized porous materials, which exhibit excellent absorption capacity and good catalytic activity for CO<sub>2</sub>. As a result, they are extensively utilized in the chemical conversion of CO<sub>2</sub>. This paper specifically focuses on the utilization of ILs-functionalized organic porous materials, ILs-functionalized inorganic porous materials, and ILs-functionalized organic-inorganic hybrid porous materials in the conversion of CO<sub>2</sub>. The synergistic effects of combining ILs with porous materials in CO<sub>2</sub> conversion are thoroughly discussed. Furthermore, an in-depth analysis is provided regarding the potential prospects and future applications of utilizing ILs-functionalized porous materials within the broader realm of catalytic CO<sub>2</sub> conversion technologies.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 11","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-08-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142227009","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Organoselenium Compounds as an Emerging Class of Stabilizers of applied Nanomaterials for Applications in the Catalysis of Organic Reactions 有机硒化合物作为一类新兴的应用纳米材料稳定剂在有机反应催化中的应用
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2024-08-16 DOI: 10.1002/ajoc.202400174
Suraj Purohit, Preeti Oswal, Anupma Tyagi, Anurag Bahuguna, Neeraj Bhatt, Arun Kumar
{"title":"Organoselenium Compounds as an Emerging Class of Stabilizers of applied Nanomaterials for Applications in the Catalysis of Organic Reactions","authors":"Suraj Purohit,&nbsp;Preeti Oswal,&nbsp;Anupma Tyagi,&nbsp;Anurag Bahuguna,&nbsp;Neeraj Bhatt,&nbsp;Arun Kumar","doi":"10.1002/ajoc.202400174","DOIUrl":"10.1002/ajoc.202400174","url":null,"abstract":"<p>Nanomaterials have revolutionized various scientific and industrial domains due to their exceptional properties and diverse applications. Yet, challenges persist in achieving their controlled synthesis, stability, and recyclability, especially in catalysis. Organoselenium compounds are emerging as promising agents for the stabilization of nanomaterials, with high prospects for catalytic applications. This article covers the recent strides made in harnessing the potential of organoselenium compounds to stabilize diverse nanomaterials with applications in catalysis. Specifically, it delves into their effectiveness in Suzuki-Miyaura cross-coupling, C−O coupling, Sonogashira coupling, reduction of nitroarenes, synthesis of primary amides (in aqueous medium), and offers a comprehensive overview of this evolving field.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 9","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-08-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142217026","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Visible-Light-Enabled Dual-Catalysis Approach to Stereoselective [2+2] Cycloaddition of Erlenmeyer-Plöchl Azlactones 利用可见光的双催化方法实现埃伦梅尔-普洛尔氮杂环内酯的立体选择性 [2 + 2] 环加成反应
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2024-08-16 DOI: 10.1002/ajoc.202400271
Dr. Isabella F. S. Marra, Ms. Larissa P. Silva, Dr. Pedro P. De Castro, Dr. Leonã S. Flores, Dr. Kleber T. De Oliveira, Dr. Paulo E. N. De Souza, Dr. Brenno A. D. Neto, Dr. Hélio F. Dos Santos, Dr. Giovanni W. Amarante
{"title":"Visible-Light-Enabled Dual-Catalysis Approach to Stereoselective [2+2] Cycloaddition of Erlenmeyer-Plöchl Azlactones","authors":"Dr. Isabella F. S. Marra,&nbsp;Ms. Larissa P. Silva,&nbsp;Dr. Pedro P. De Castro,&nbsp;Dr. Leonã S. Flores,&nbsp;Dr. Kleber T. De Oliveira,&nbsp;Dr. Paulo E. N. De Souza,&nbsp;Dr. Brenno A. D. Neto,&nbsp;Dr. Hélio F. Dos Santos,&nbsp;Dr. Giovanni W. Amarante","doi":"10.1002/ajoc.202400271","DOIUrl":"10.1002/ajoc.202400271","url":null,"abstract":"<p>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-(<i>zeta</i>)-<i>Z</i>,<i>E</i>-isomers were isolated in good yields and with high regio- and diastereoselectivity (in all cases, &gt;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.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 11","pages":""},"PeriodicalIF":2.8,"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}
引用次数: 0
Silane-Mediated Alkylation of Arenes via Reductive Friedel-Crafts Reaction Using Carbonyl Compounds 硅烷通过羰基化合物的还原 Friedel-Crafts 反应介导的烯烃烷基化反应
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2024-08-16 DOI: 10.1002/ajoc.202400347
Jabir Khan, Rina Mahato,  Kanhaiya, Chinmoy Kumar Hazra
{"title":"Silane-Mediated Alkylation of Arenes via Reductive Friedel-Crafts Reaction Using Carbonyl Compounds","authors":"Jabir Khan,&nbsp;Rina Mahato,&nbsp; Kanhaiya,&nbsp;Chinmoy Kumar Hazra","doi":"10.1002/ajoc.202400347","DOIUrl":"10.1002/ajoc.202400347","url":null,"abstract":"<p>A metal-free one-pot synthesis route has been documented for the production of 1,1-unsymmetrical di-aryl alkanes <i>via</i> 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 (Me<sub>2</sub>SiClH) reduction, succeeded <i>via</i> nucleophilic attack of arenes. The established protocol demonstrates a promising strategy for converting indoline-2,3-dione into <i>α</i>-aryl oxindoles with high yields. The reaction involves reduction with Me<sub>2</sub>SiClH, followed by the attack of arenes in the presence of a TfOH catalyst. The devised protocol offers scalability and remarkable tolerance towards various functional groups. Control experiments provide insights into the reaction mechanism, highlighting the crucial roles of HFIP and Me<sub>2</sub>SiClH. 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 efficiently synthesising the anticoagulant drug Phenprocoumon and the rodent control agent Coumatetralyl.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 11","pages":""},"PeriodicalIF":2.8,"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}
引用次数: 0
In Situ Generation of Quinoliziniums for Dual Visible Light-Induced Gold(III)-Catalyzed Alkynylation and Peptide Modification 原位生成喹嗪鎓，用于可见光诱导的金（III）催化炔化和多肽修饰
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2024-08-15 DOI: 10.1002/ajoc.202400339
Wa-Yi O, Ajcharapan Tantipanjaporn, Jie-Ren Deng, Rui Tang, Karen Ka-Yan Kung, Hoi-Yi Sit, Chun-Him Nathanael Lai, Man-Kin Wong
{"title":"In Situ Generation of Quinoliziniums for Dual Visible Light-Induced Gold(III)-Catalyzed Alkynylation and Peptide Modification","authors":"Wa-Yi O,&nbsp;Ajcharapan Tantipanjaporn,&nbsp;Jie-Ren Deng,&nbsp;Rui Tang,&nbsp;Karen Ka-Yan Kung,&nbsp;Hoi-Yi Sit,&nbsp;Chun-Him Nathanael Lai,&nbsp;Man-Kin Wong","doi":"10.1002/ajoc.202400339","DOIUrl":"10.1002/ajoc.202400339","url":null,"abstract":"<p>A new approach of dual visible light-induced gold(III)-catalyzed alkynylation and its application in selective modification of alkyne-linked peptides has been developed. The bis-cyclometalated gold(III) complex exhibited dual roles of (1) <i>in situ</i> generation of quinolizinium-based photosensitizer (λ<sub>em</sub>=500 – 594 nm) and (2) alkynylation of iminium ions. Under optimized conditions, alkynylated products were afforded in good yields up to 73 %. The application of this strategy in selective modification of alkyne-linked peptides gave modified peptides in up to 67 % conversion. Our dual visible light/gold(III) catalysis exemplifies the potential of merging photocatalysis and transition metal catalysis to develop novel bioconjugation.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 11","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-08-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142227044","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
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) 封面：利用三苯基二氯化铋介导的 S-N 键形成反应合成苯并唑-2-硫醚与伯胺和仲胺的亚磺酰胺(亚洲有机化学杂志 8/2024)
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2024-08-14 DOI: 10.1002/ajoc.202480801
Arisu Koyanagi, Dr. Yuki Murata, Dr. Mio Matsumura, Prof. Dr. Shuji Yasuike
{"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,&nbsp;Dr. Yuki Murata,&nbsp;Dr. Mio Matsumura,&nbsp;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":"13 8","pages":""},"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}
引用次数: 0
Recent Advances in Scandium(III) Triflate Catalysis: A Review 三氟化硫钪（III）催化的最新进展：综述
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2024-08-14 DOI: 10.1002/ajoc.202400295
Sumit Kumar, Aditi Arora, Shivani Sapra, Riya Chaudhary, Prof. Brajendra K. Singh, Dr. Sunil K. Singh
{"title":"Recent Advances in Scandium(III) Triflate Catalysis: A Review","authors":"Sumit Kumar,&nbsp;Aditi Arora,&nbsp;Shivani Sapra,&nbsp;Riya Chaudhary,&nbsp;Prof. Brajendra K. Singh,&nbsp;Dr. Sunil K. Singh","doi":"10.1002/ajoc.202400295","DOIUrl":"10.1002/ajoc.202400295","url":null,"abstract":"<p>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)<sub>3</sub>] stands out as a water-resistant Lewis acid with remarkable catalytic activity in aqueous environments. Unlike typical Lewis acids such as AlCl<sub>3</sub>, BF<sub>3</sub>, and SnCl<sub>4</sub>, which are decomposed or deactivated by water, Sc(OTf)<sub>3</sub> 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)<sub>3</sub> in water is attributed to the smaller size of scandium ions (Sc<sup>3+</sup>), enhancing its catalytic efficiency. Sc(OTf)<sub>3</sub> 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)<sub>3</sub> over the past decade underscores the necessity for updated insights. This review provides a concise overview of the versatility of Sc(OTf)<sub>3</sub> as a catalyst, focusing on developments from 2017 to 2024.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 11","pages":""},"PeriodicalIF":2.8,"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}
引用次数: 0
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