N‐heterocyclic carbene (NHC) catalyzed reactions of carboxylic acids play a crucial role in NHC catalysis, enabling the formation of chiral and achiral functional molecules. In this review, the achievements in NHC catalyzed activations of carboxylic acids are summarized, and an outlook on future research directions is also provided.
{"title":"N‐Heterocyclic Carbene Catalyzed Activation of Carboxylic Acids","authors":"Yueling Qin , Tingting Li","doi":"10.1002/ajoc.202400585","DOIUrl":"10.1002/ajoc.202400585","url":null,"abstract":"<div><div>N‐heterocyclic carbene (NHC) catalyzed reactions of carboxylic acids play a crucial role in NHC catalysis, enabling the formation of chiral and achiral functional molecules. In this review, the achievements in NHC catalyzed activations of carboxylic acids are summarized, and an outlook on future research directions is also provided.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 2","pages":"Article e202400585"},"PeriodicalIF":2.8,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143424187","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}
Jing Li , Bao‐Sen Xu , Xinglong‐Zhang , Le‐Le Zhao , Shao‐Zhe Yi , Bao‐Ning Li
The optical materials based on excited state intramolecular proton transfer (ESIPT) have garnered significant attention due to their unique photophysical properties and applications in sensors and imaging agents (probes). These materials exhibit an intrinsic four‐level photocycle scheme through the enol (E)‐keto (K) phototautomerization process, resulting in a large Stokes shift, environmental sensitivity, and potential for ratiometric sensing. This review primarily focuses on elucidating the luminescence mechanism and structure‐property relationships of recent ESIPT molecules, as well as exploring the sensing applications of phosphorescent functional materials.
{"title":"Recent Advances in Smart Sensing Based on Excited‐State Intramolecular Proton‐Transfer (ESIPT)‐Inspired Emitters","authors":"Jing Li , Bao‐Sen Xu , Xinglong‐Zhang , Le‐Le Zhao , Shao‐Zhe Yi , Bao‐Ning Li","doi":"10.1002/ajoc.202400572","DOIUrl":"10.1002/ajoc.202400572","url":null,"abstract":"<div><div>The optical materials based on excited state intramolecular proton transfer (ESIPT) have garnered significant attention due to their unique photophysical properties and applications in sensors and imaging agents (probes). These materials exhibit an intrinsic four‐level photocycle scheme through the enol (E)‐keto (K) phototautomerization process, resulting in a large Stokes shift, environmental sensitivity, and potential for ratiometric sensing. This review primarily focuses on elucidating the luminescence mechanism and structure‐property relationships of recent ESIPT molecules, as well as exploring the sensing applications of phosphorescent functional materials.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 2","pages":"Article e202400572"},"PeriodicalIF":2.8,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143424322","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}
Two covalently linked fluorescent tetrads containing two BODIPY units and two 3‐pyrrolyl BODIPY units have been synthesized over a sequence of steps starting with bis(3‐pyrrolyl BODIPY) as the key precursor. Both covalently linked tetrads 6 and 7 were confirmed by HR‐MS and characterized and studied by 1D and 2D NMR, absorption, cyclic voltammetry, steady state and time‐resolved fluorescence techniques, and also by DFT and TD‐DFT methods. The tetrad 6 exhibited one strong absorption band at 680 nm whereas the tetrad 7 showed strong absorption bands at 510 nm and 648 nm corresponding to BODIPY and 3‐pyrrolyl BODIPY units respectively and the absorption band of tetrad 6 was bathochromically shifted due to effective π‐conjugation in tetrad 6 compared to tetrad 7. The electrochemical studies revealed that tetrads exhibit only two reductions indicating their electron deficient nature. The steady state and time‐resolved fluorescence studies invoked a possibility of singlet‐singlet energy transfer from BODIPY units to 3‐pyrrolyl BODIPY units in one of the tetrads upon selective excitation of BODIPY unit. In this tetrad, the BODIPY unit acts as an energy donor whereas the 3‐pyrrolyl BODIPY unit acts as an energy acceptor. The theoretical studies were corroborated with experimental results. Group webpage: https://ravikanthlab.wixsite.com/mysite/.
{"title":"Synthesis and Properties of Covalently Linked Fluorescent Tetrads Containing Two BODIPYs and Two 3‐Pyrrolyl BODIPYs","authors":"Pinky Chauhan , Prof. Mangalampalli Ravikanth","doi":"10.1002/ajoc.202400551","DOIUrl":"10.1002/ajoc.202400551","url":null,"abstract":"<div><div>Two covalently linked fluorescent tetrads containing two BODIPY units and two 3‐pyrrolyl BODIPY units have been synthesized over a sequence of steps starting with bis(3‐pyrrolyl BODIPY) as the key precursor. Both covalently linked tetrads <strong>6</strong> and <strong>7</strong> were confirmed by HR‐MS and characterized and studied by 1D and 2D NMR, absorption, cyclic voltammetry, steady state and time‐resolved fluorescence techniques, and also by DFT and TD‐DFT methods. The tetrad <strong>6</strong> exhibited one strong absorption band at 680 nm whereas the tetrad <strong>7</strong> showed strong absorption bands at 510 nm and 648 nm corresponding to BODIPY and 3‐pyrrolyl BODIPY units respectively and the absorption band of tetrad <strong>6</strong> was bathochromically shifted due to effective π‐conjugation in tetrad <strong>6</strong> compared to tetrad <strong>7</strong>. The electrochemical studies revealed that tetrads exhibit only two reductions indicating their electron deficient nature. The steady state and time‐resolved fluorescence studies invoked a possibility of singlet‐singlet energy transfer from BODIPY units to 3‐pyrrolyl BODIPY units in one of the tetrads upon selective excitation of BODIPY unit. In this tetrad, the BODIPY unit acts as an energy donor whereas the 3‐pyrrolyl BODIPY unit acts as an energy acceptor. The theoretical studies were corroborated with experimental results. Group webpage: <span><span>https://ravikanthlab.wixsite.com/mysite/</span><svg><path></path></svg></span>.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 2","pages":"Article e202400551"},"PeriodicalIF":2.8,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143423881","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. Tomohiro Umeno , Mio Tanaka , Moeka Fujihara , Naoko Iizuka , Shota Matsumoto , Dr. Kazuteru Usui , Prof. Satoru Karasawa
Guanidine is strongly basic and has a high molecular recognition ability. We previously developed a guanidine‐bearing benzoquinoline for the fluorescence detection of MeOH by exploiting the strong basicity of guanidine. The benzoquinoline fluorophore quantitatively detected MeOH in EtOH with moderate sensitivity and a limit of detection (LOD) of 16.5 %. In this study, we developed two guanidinyl boron dipyrromethene (BODIPY) and two guanidinyl coumarin fluorophores. These fluorophores have higher molar extinction coefficients (ϵ) than those of benzoquinolines, which suggests that they could have improved detection sensitivity. The BODIPY fluorophores exhibited acid‐responsive turn‐on fluorescence for MeOH, similar to the benzoquinoline fluorophore. Their high ϵ values led to an enhanced MeOH detection sensitivity of 1.3 % in EtOH. The coumarin derivatives exhibited acid‐responsive turn‐off fluorescence. In addition, the absorbance spectral shift of the protonated and neutral forms of coumarin enabled the ratiometric detection of MeOH (LOD=0.85 % and 0.57 %, respectively). This study demonstrates the utility of guanidine‐based fluorophores in molecular recognition and promotes the development of similar fluorophores in analytical chemistry.
{"title":"Advanced pH Indicators Consisting of BODIPY and Coumarin Fluorophores with a Guanidinyl Structure Capable of Methanol Recognition","authors":"Dr. Tomohiro Umeno , Mio Tanaka , Moeka Fujihara , Naoko Iizuka , Shota Matsumoto , Dr. Kazuteru Usui , Prof. Satoru Karasawa","doi":"10.1002/ajoc.202400605","DOIUrl":"10.1002/ajoc.202400605","url":null,"abstract":"<div><div>Guanidine is strongly basic and has a high molecular recognition ability. We previously developed a guanidine‐bearing benzoquinoline for the fluorescence detection of MeOH by exploiting the strong basicity of guanidine. The benzoquinoline fluorophore quantitatively detected MeOH in EtOH with moderate sensitivity and a limit of detection (LOD) of 16.5 %. In this study, we developed two guanidinyl boron dipyrromethene (BODIPY) and two guanidinyl coumarin fluorophores. These fluorophores have higher molar extinction coefficients (ϵ) than those of benzoquinolines, which suggests that they could have improved detection sensitivity. The BODIPY fluorophores exhibited acid‐responsive turn‐on fluorescence for MeOH, similar to the benzoquinoline fluorophore. Their high ϵ values led to an enhanced MeOH detection sensitivity of 1.3 % in EtOH. The coumarin derivatives exhibited acid‐responsive turn‐off fluorescence. In addition, the absorbance spectral shift of the protonated and neutral forms of coumarin enabled the ratiometric detection of MeOH (LOD=0.85 % and 0.57 %, respectively). This study demonstrates the utility of guanidine‐based fluorophores in molecular recognition and promotes the development of similar fluorophores in analytical chemistry.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 2","pages":"Article e202400605"},"PeriodicalIF":2.8,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143424257","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}
Sundararajan Suresh , Pari Keerthana , Prof. Dr. Fazlurrahman Nawaz Khan
An efficient method has been developed for the green synthesis of alkylated quinolines via Cu‐TEMPO catalyzed dehydrogenation, and DEP/DES‐assisted benzylic C−H functionalization followed by cross Rauhut‐Currier type reaction. The reaction mechanism is elucidated through control experiments and 1H NMR reaction monitoring. This transformation offers several advantages, including moderate to good yields of the desired products, mild reaction conditions, use of a cost‐effective metal catalyst, good functional group tolerance, and applicability to gram‐scale synthesis. Additionally, the synthetic utility and the photophysical properties of the synthesized alkylated quinoline derivatives were investigated.
{"title":"Alkylated Quinolines through Benzylic sp3 C−H Functionalization: Sequential Synthesis and Photophysical Studies","authors":"Sundararajan Suresh , Pari Keerthana , Prof. Dr. Fazlurrahman Nawaz Khan","doi":"10.1002/ajoc.202400607","DOIUrl":"10.1002/ajoc.202400607","url":null,"abstract":"<div><div>An efficient method has been developed for the green synthesis of alkylated quinolines <em>via</em> Cu‐TEMPO catalyzed dehydrogenation, and DEP/DES‐assisted benzylic C−H functionalization followed by cross Rauhut‐Currier type reaction. The reaction mechanism is elucidated through control experiments and <sup>1</sup>H NMR reaction monitoring. This transformation offers several advantages, including moderate to good yields of the desired products, mild reaction conditions, use of a cost‐effective metal catalyst, good functional group tolerance, and applicability to gram‐scale synthesis. Additionally, the synthetic utility and the photophysical properties of the synthesized alkylated quinoline derivatives were investigated.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 2","pages":"Article e202400607"},"PeriodicalIF":2.8,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143423677","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}
Emissive organic semiconductors are crucial for integrated optoelectronic devices, yet only a limited number of materials exhibit high mobility and high photoluminescence quantum yield because of the contradictory requirements for molecular stacking. In this study, two diphenylperylene isomers, 39P‐Ph and 310P‐Ph, were successfully synthesized through a one‐step process by varying the positions of the substituent phenyl groups on the perylene core. Both compounds were comprehensively characterized and demonstrated excellent hole transport capabilities and moderate photoluminescence quantum yield (PLQY), along with long‐wavelength emission, establishing them as effective emissive organic semiconductors. 39P‐Ph emits orange‐yellow fluorescence in crystalline powder with an absolute PLQY of 15.4 % and 310P‐Ph shows orange‐red emission with an emissive wavelength of up to 612 nm in 17.5 % PLQY. Moreover, the carrier mobilities of 39P‐Ph and 310P‐Ph are up to 3.05 cm2 V−1 s−1 and 1.36 cm2 V−1 s−1, respectively, based on the single‐crystal devices. These results reveal that 39P‐Ph and 310P‐Ph are promising candidates as emissive semiconductors, offering a balance between efficient charge transport and light emission for integrated optoelectronic applications.
{"title":"Diphenylperylene Isomers as Novel Emissive Organic Semiconductors","authors":"Liangliang Chen , Ying Wang , Zitong Liu","doi":"10.1002/ajoc.202400608","DOIUrl":"10.1002/ajoc.202400608","url":null,"abstract":"<div><div>Emissive organic semiconductors are crucial for integrated optoelectronic devices, yet only a limited number of materials exhibit high mobility and high photoluminescence quantum yield because of the contradictory requirements for molecular stacking. In this study, two diphenylperylene isomers, <strong>39P‐Ph</strong> and <strong>310P‐Ph</strong>, were successfully synthesized through a one‐step process by varying the positions of the substituent phenyl groups on the perylene core. Both compounds were comprehensively characterized and demonstrated excellent hole transport capabilities and moderate photoluminescence quantum yield (PLQY), along with long‐wavelength emission, establishing them as effective emissive organic semiconductors. <strong>39P‐Ph</strong> emits orange‐yellow fluorescence in crystalline powder with an absolute PLQY of 15.4 % and <strong>310P‐Ph</strong> shows orange‐red emission with an emissive wavelength of up to 612 nm in 17.5 % PLQY. Moreover, the carrier mobilities of <strong>39P‐Ph</strong> and <strong>310P‐Ph</strong> are up to 3.05 cm<sup>2</sup> V<sup>−1</sup> s<sup>−1</sup> and 1.36 cm<sup>2</sup> V<sup>−1</sup> s<sup>−1</sup>, respectively, based on the single‐crystal devices. These results reveal that <strong>39P‐Ph</strong> and <strong>310P‐Ph</strong> are promising candidates as emissive semiconductors, offering a balance between efficient charge transport and light emission for integrated optoelectronic applications.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 2","pages":"Article e202400608"},"PeriodicalIF":2.8,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143423678","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}
Vinay S. Sharma , Saloni Mishra , Anuj S. Sharma , Neha Sharma , Rajender S. Varma , Pranav S. Shrivastav , Achalkumar Ammathnadu Sudhakar
The utilization of microcrystalline cellulose (MCC) and cellulose nanocrystals (CNC) as supports for nanocatalysts has garnered considerable interest in recent research due to their unique properties and several advantages. In this regard, we present a review of the use of MCC or CNC‐based nanocatalysts and their catalytic performance in organic reactions under milder and sustainable reaction conditions. The inherent advantages of MCC, such as its abundance, biocompatibility, and versatile surface, make it more attractive support material for nanocatalysts. Similarly, CNCs, with their high surface area, tunable surface chemistry, and sustainable nature, offer promising prospects for enhancing catalytic processes. The synergy between the cellulose‐based material and nanoparticles exhibits several novel properties. This review highlights the key features, advantages, and catalytic applications of MCC as well as CNC‐supported nanocatalysts, emphasizing their role in promoting more sustainable and efficient organic transformations.
{"title":"Microcrystalline Cellulose and Cellulose Nanocrystals: Ecofriendly and Sustainable Support Materials in Heterogeneous Nanocatalysis for Green Organic Transformations","authors":"Vinay S. Sharma , Saloni Mishra , Anuj S. Sharma , Neha Sharma , Rajender S. Varma , Pranav S. Shrivastav , Achalkumar Ammathnadu Sudhakar","doi":"10.1002/ajoc.202400586","DOIUrl":"10.1002/ajoc.202400586","url":null,"abstract":"<div><div>The utilization of microcrystalline cellulose (MCC) and cellulose nanocrystals (CNC) as supports for nanocatalysts has garnered considerable interest in recent research due to their unique properties and several advantages. In this regard, we present a review of the use of MCC or CNC‐based nanocatalysts and their catalytic performance in organic reactions under milder and sustainable reaction conditions. The inherent advantages of MCC, such as its abundance, biocompatibility, and versatile surface, make it more attractive support material for nanocatalysts. Similarly, CNCs, with their high surface area, tunable surface chemistry, and sustainable nature, offer promising prospects for enhancing catalytic processes. The synergy between the cellulose‐based material and nanoparticles exhibits several novel properties. This review highlights the key features, advantages, and catalytic applications of MCC as well as CNC‐supported nanocatalysts, emphasizing their role in promoting more sustainable and efficient organic transformations.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 2","pages":"Article e202400586"},"PeriodicalIF":2.8,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143423703","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}
You‐Qiang Guo , Long Liang , Dr. Zhen‐Yu Wang , Prof. Xiang Wu , Prof. You‐Gui Li
A TEMPO‐mediated method has been developed for the synthesis of bis(indolyl)‐methane derivatives by the cross‐dehydrogenative coupling between C(sp3)−H of para‐cresol derivatives and C(sp2)−H of indoles in moderate yields under aqueous conditions. This method utilizes toluene derivatives as starting materials, allowing for coupling without the need for further functionalization. The use of environmentally friendly water as a solvent minimizes waste generation. Electron‐donating groups such as methyl and methoxy, as well as halogens like fluorine, chlorine, and bromine, exhibit good tolerance in this process. Furthermore, a possible reaction mechanism is proposed to elucidate the formation of BIMs.
通过对位甲酚衍生物的 C(sp3)-H与吲哚的 C(sp2)-H之间的交叉脱氢偶联，开发了一种 TEMPO 氧化法合成双(吲哚基)甲烷衍生物，在水溶液条件下产量适中。这种方法在避免预官能化、使用水作为溶剂和容忍各种官能团方面具有显著优势。
{"title":"TEMPO‐Mediated Cross‐Dehydrogenative Coupling for the Synthesis of Bis(indolyl)methanes","authors":"You‐Qiang Guo , Long Liang , Dr. Zhen‐Yu Wang , Prof. Xiang Wu , Prof. You‐Gui Li","doi":"10.1002/ajoc.202400484","DOIUrl":"10.1002/ajoc.202400484","url":null,"abstract":"<div><div>A TEMPO‐mediated method has been developed for the synthesis of bis(indolyl)‐methane derivatives by the cross‐dehydrogenative coupling between C(sp<sup>3</sup>)−H of <em>para‐</em>cresol derivatives and C(sp<sup>2</sup>)−H of indoles in moderate yields under aqueous conditions. This method utilizes toluene derivatives as starting materials, allowing for coupling without the need for further functionalization. The use of environmentally friendly water as a solvent minimizes waste generation. Electron‐donating groups such as methyl and methoxy, as well as halogens like fluorine, chlorine, and bromine, exhibit good tolerance in this process. Furthermore, a possible reaction mechanism is proposed to elucidate the formation of BIMs.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 2","pages":"Article e202400484"},"PeriodicalIF":2.8,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142665592","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}
Zhe Tian , Zhaoxuan Zeng , Hongqiang Xie , Prof. Qing Liu , Dr. Fachao Yan , Prof. Hui Liu
A novel unconventional redox‐neutral regioselective iodoamination of allenamides was developed. In the absence of metal catalyst, base and oxidant, the selective iodoamination of allenamides was achieved by using iodide salt in combination with morpholine/imidazole. The Iodide‐substituted Z‐enamides were synthesized under mild reaction conditions, and the products were stable and highly amenable to further modification.
{"title":"An Unconventional Redox‐Neutral Regioselective Iodoamination of Allenamides","authors":"Zhe Tian , Zhaoxuan Zeng , Hongqiang Xie , Prof. Qing Liu , Dr. Fachao Yan , Prof. Hui Liu","doi":"10.1002/ajoc.202400667","DOIUrl":"10.1002/ajoc.202400667","url":null,"abstract":"<div><div>A novel unconventional redox‐neutral regioselective iodoamination of allenamides was developed. In the absence of metal catalyst, base and oxidant, the selective iodoamination of allenamides was achieved by using iodide salt in combination with morpholine/imidazole. The Iodide‐substituted <em>Z</em>‐enamides were synthesized under mild reaction conditions, and the products were stable and highly amenable to further modification.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 2","pages":"Article e202400667"},"PeriodicalIF":2.8,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143423907","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}
Qichao Zhang , Fang Zhang , Zhihang Wei , Xiangyi Shi , Lin He , Jichang Liu , Guangfen Du
A tandem annulation reaction of allyl ketones and β‐aryl ethenesulfonyl fluorides has been described. Under the catalysis of Brønsted base, allyl ketones reacted with β‐aryl ethenesulfonyl fluorides through a tandem intermolecular Michael addition‐intramolecular SuFEx process to afford γ‐alkenylated δ‐sultones in good to excellent yields. In this reaction, no additional base was needed, and 4 Å molecular sieves were used as efficient HF scavenger to restrict the neutralization and deactivation of the Brønsted base catalyst.
{"title":"Synthesis of γ‐Alkenylated δ‐Sultones Via Brønsted Base‐Catalyzed Annulative SuFEx Reaction of Allyl Ketones and Ethenesulfonyl Fluorides","authors":"Qichao Zhang , Fang Zhang , Zhihang Wei , Xiangyi Shi , Lin He , Jichang Liu , Guangfen Du","doi":"10.1002/ajoc.202400619","DOIUrl":"10.1002/ajoc.202400619","url":null,"abstract":"<div><div>A tandem annulation reaction of allyl ketones and β‐aryl ethenesulfonyl fluorides has been described. Under the catalysis of Brønsted base, allyl ketones reacted with β‐aryl ethenesulfonyl fluorides through a tandem intermolecular Michael addition‐intramolecular SuFEx process to afford γ‐alkenylated δ‐sultones in good to excellent yields. In this reaction, no additional base was needed, and 4 Å molecular sieves were used as efficient HF scavenger to restrict the neutralization and deactivation of the Brønsted base catalyst.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 2","pages":"Article e202400619"},"PeriodicalIF":2.8,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143424309","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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