Pub Date : 2025-01-23DOI: 10.1016/j.tet.2025.134489
Péter Szuroczki , Laura Barbara Jenei , Viktor Sándor , Attila Bényei , László Kollár
Imidazo[1,2-a]pyridines possessing carboxamido and ester functionalities in 2- and 6-positions were synthesised in palladium-catalysed amino- and alkoxy/aryloxycarbonylation using a great variety of amines and alcohols/phenols as N- and O-nucleophiles, respectively. The corresponding iodoheteroaromatics, used as substrates, were synthesised from the substituted 2-aminopyridines, terminal alkynes and iodine in copper-catalysed oxidative ring-closure─iodination reaction sequence. Mono- and dinuclear copper-2-aminopyridine complexes, used as pre-formed catalysts, were characterised by X-ray crystallography. The amides and esters were obtained in moderate to high yields mainly depending on the nucleophile and not on the structure of the 2-iodo[1,2-a]pyridine substrates.
{"title":"Synthesis and functionalization of 2-iodoimidazo[1,2-a]pyridines in palladium-catalysed amino-, aryloxy- and alkoxycarbonylations","authors":"Péter Szuroczki , Laura Barbara Jenei , Viktor Sándor , Attila Bényei , László Kollár","doi":"10.1016/j.tet.2025.134489","DOIUrl":"10.1016/j.tet.2025.134489","url":null,"abstract":"<div><div>Imidazo[1,2-<em>a</em>]pyridines possessing carboxamido and ester functionalities in 2- and 6-positions were synthesised in palladium-catalysed amino- and alkoxy/aryloxycarbonylation using a great variety of amines and alcohols/phenols as <em>N</em>- and <em>O</em>-nucleophiles, respectively. The corresponding iodoheteroaromatics, used as substrates, were synthesised from the substituted 2-aminopyridines, terminal alkynes and iodine in copper-catalysed oxidative ring-closure─iodination reaction sequence. Mono- and dinuclear copper-2-aminopyridine complexes, used as pre-formed catalysts, were characterised by X-ray crystallography. The amides and esters were obtained in moderate to high yields mainly depending on the nucleophile and not on the structure of the 2-iodo[1,2-<em>a</em>]pyridine substrates.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"174 ","pages":"Article 134489"},"PeriodicalIF":2.1,"publicationDate":"2025-01-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143342945","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-01-23DOI: 10.1016/j.tet.2025.134494
Ekaterina A. Verochkina, Victoria G. Fedoseeva, Evgeniy V. Kondrashov, Igor B. Rozentsveig, Ludmila I. Larina, Alexander V. Vashchenko, Nadezhda V. Vchislo
The reaction of 2,5-disubstituted (Z,E)-pent-2-en-4-ynals with secondary amines and thiols has been studied. It is found that only the triple bond is subjected to nucleophilic attack. The interaction of polyunsaturated aldehydes with piperazine leads to a mixture of addition products at the triple bond with the participation of one or both NH-groups. Organogermanium enynal - 2-(butylthio)-5-(triethylgermyl)pent-2-en-4-ynal, gives products of addition at the triple bond with pyrrolidine both with retention and with cleavage of the triethylgermyl group. The regioselectivity of the addition of nucleophiles to α-substituted enyne aldehydes is explained within the framework of DFT methods by comparing both the reactivity indices for competing electrophilic centers (electrophilic Parr functions) and the thermodynamic stability of the resulting products.
{"title":"Regioselectivity of conjugate addition of secondary amines and thiols to α-substituted enyne aldehydes","authors":"Ekaterina A. Verochkina, Victoria G. Fedoseeva, Evgeniy V. Kondrashov, Igor B. Rozentsveig, Ludmila I. Larina, Alexander V. Vashchenko, Nadezhda V. Vchislo","doi":"10.1016/j.tet.2025.134494","DOIUrl":"10.1016/j.tet.2025.134494","url":null,"abstract":"<div><div>The reaction of 2,5-disubstituted (<em>Z,E</em>)-pent-2-en-4-ynals with secondary amines and thiols has been studied. It is found that only the triple bond is subjected to nucleophilic attack. The interaction of polyunsaturated aldehydes with piperazine leads to a mixture of addition products at the triple bond with the participation of one or both NH-groups. Organogermanium enynal - 2-(butylthio)-5-(triethylgermyl)pent-2-en-4-ynal, gives products of addition at the triple bond with pyrrolidine both with retention and with cleavage of the triethylgermyl group. The regioselectivity of the addition of nucleophiles to α-substituted enyne aldehydes is explained within the framework of DFT methods by comparing both the reactivity indices for competing electrophilic centers (electrophilic Parr functions) and the thermodynamic stability of the resulting products.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"174 ","pages":"Article 134494"},"PeriodicalIF":2.1,"publicationDate":"2025-01-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143343117","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-01-23DOI: 10.1016/j.tet.2025.134495
Wen-Long Wang, Xiao-Xiong Lv, Fei Chen, Ning Liu, Zhi-Hong Du
An efficient catalytic system based on a copper–amine complex was developed for the oxidative cross-coupling of 3-hydroxy-2-naphthoic acid derivatives and 2-naphthols under mild conditions. The method tolerated a broad substrate scope, and a series of C1-symmetrical BINOL derivatives were obtained in excellent yields (up to 93 %). In addition, the model reaction was easily amplified to the gram scale with a relatively consistent yield. The control experiments showed that in this catalytic system, the homocoupling reactions of 2-naphthol derivatives do not take place, and the degree of homocoupling for the 3-hydroxy-2-naphthoic acid derivatives did not exceed 10 %, thereby indicating a high chemical selectivity. At last, a possible mechanism was proposed based on high-resolution mass spectrometry and previous studies.
{"title":"Copper–amine-complex-catalyzed highly selective oxidative cross-coupling of 2-naphthols: Synthesis of C1-Symmetric BINOLs","authors":"Wen-Long Wang, Xiao-Xiong Lv, Fei Chen, Ning Liu, Zhi-Hong Du","doi":"10.1016/j.tet.2025.134495","DOIUrl":"10.1016/j.tet.2025.134495","url":null,"abstract":"<div><div>An efficient catalytic system based on a copper–amine complex was developed for the oxidative cross-coupling of 3-hydroxy-2-naphthoic acid derivatives and 2-naphthols under mild conditions. The method tolerated a broad substrate scope, and a series of <em>C</em><sub><em>1</em></sub>-symmetrical BINOL derivatives were obtained in excellent yields (up to 93 %). In addition, the model reaction was easily amplified to the gram scale with a relatively consistent yield. The control experiments showed that in this catalytic system, the homocoupling reactions of 2-naphthol derivatives do not take place, and the degree of homocoupling for the 3-hydroxy-2-naphthoic acid derivatives did not exceed 10 %, thereby indicating a high chemical selectivity. At last, a possible mechanism was proposed based on high-resolution mass spectrometry and previous studies.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"174 ","pages":"Article 134495"},"PeriodicalIF":2.1,"publicationDate":"2025-01-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143343118","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-01-23DOI: 10.1016/j.tet.2025.134486
Ali Akbari, Danial Zand Hosein shahi, Ali Rahimabadi
Copper oxide-Titanium dioxide nanocomposites (CuO/TiO2 NC) is an efficient photocatalyst for the synthesis of 2H-indazoles derivatives through intermolecular C–N bond (Ullmann Goldberg reaction) and intramolecular N–N bond formation. The CuO/TiO2 NC is a stable photocatalyst and can be reused multiple times without losing its catalytic properties. High yields of product, environmentally friendly, cost-effective method, and easy workup are advantages of the present method. All synthesized compounds were characterized by NMR spectroscopy.
{"title":"Visible‐light‐mediated synthesis of 2H-indazoles from (2-bromo-benzylidene)-phenyl-amine derivatives by the Ullmann Goldberg reaction","authors":"Ali Akbari, Danial Zand Hosein shahi, Ali Rahimabadi","doi":"10.1016/j.tet.2025.134486","DOIUrl":"10.1016/j.tet.2025.134486","url":null,"abstract":"<div><div>Copper oxide-Titanium dioxide nanocomposites (CuO/TiO<sub>2</sub> NC) is an efficient photocatalyst for the synthesis of 2<em>H</em>-indazoles derivatives through intermolecular C–N bond (Ullmann Goldberg reaction) and intramolecular N–N bond formation. The CuO/TiO<sub>2</sub> NC is a stable photocatalyst and can be reused multiple times without losing its catalytic properties. High yields of product, environmentally friendly, cost-effective method, and easy workup are advantages of the present method. All synthesized compounds were characterized by NMR spectroscopy.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"174 ","pages":"Article 134486"},"PeriodicalIF":2.1,"publicationDate":"2025-01-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143343119","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-01-23DOI: 10.1016/j.tet.2025.134496
Mianran Chao , Qin Zhang , Ge Jin , Guiwen Guo , Xuan Cheng , Duyi Shen
The direct oxidation and oxygenation of C(sp3)-H bonds has profound significance in synthetic chemistry for straightforwardly installing valuable C-O and CO bonds on bulk chemicals without pre-functionalization step. However, the development of highly efficient and selective catalytic methods under mild reactions remains to be a challenge due to the large bond dissociation energy as well as the competition oxidation among intramolecular C(sp3)-H bonds. Light-induced C(sp3)-H oxidation by organic photocatalysts should be a powerful tool since strong oxidative species could be achieved at the excited states at ambient temperature. In addition, this process will become more environmentally friendly when molecular oxygen, with high atom economy and eco-compatibility, is used as the terminal oxidant. During the past decade, the combination of photo irradiation and molecular oxygen or even air under metal-free condition, as a promising catalytic approach, has received increasing attention and become the method of choice for the activation of C(sp3)-H bonds. This review introduced briefly the pioneering works and listed detailed updates of the methodology development, synthetic applications especially in the late-stage modification of drugs or natural products, and mechanism studies on photo-promoted aerobic C(sp3)-H oxidation/oxygenation by organic catalysts from 2020 to 2024. And this review is divided by the type of organic photocatalysts used in the C-H activation reactions. The production of oxygenated compounds, such as ketone, aldehyde, alcohol, hydroperoxide, and lactone has been accomplished by various of organic photocatalysts alone or the synergistic catalysis with a co-catalyst as the indirect hydrogen atom abstractor. The reaction scope, limitation, challenge, and future opportunities in this field have been discussed as well.
{"title":"Photo-driven aerobic C(sp3)-H oxidation by organic photocatalysts: A recent review","authors":"Mianran Chao , Qin Zhang , Ge Jin , Guiwen Guo , Xuan Cheng , Duyi Shen","doi":"10.1016/j.tet.2025.134496","DOIUrl":"10.1016/j.tet.2025.134496","url":null,"abstract":"<div><div>The direct oxidation and oxygenation of C(sp<sup><strong>3</strong></sup>)-H bonds has profound significance in synthetic chemistry for straightforwardly installing valuable C-O and C<img>O bonds on bulk chemicals without pre-functionalization step. However, the development of highly efficient and selective catalytic methods under mild reactions remains to be a challenge due to the large bond dissociation energy as well as the competition oxidation among intramolecular C(sp<sup><strong>3</strong></sup>)-H bonds. Light-induced C(sp<sup><strong>3</strong></sup>)-H oxidation by organic photocatalysts should be a powerful tool since strong oxidative species could be achieved at the excited states at ambient temperature. In addition, this process will become more environmentally friendly when molecular oxygen, with high atom economy and eco-compatibility, is used as the terminal oxidant. During the past decade, the combination of photo irradiation and molecular oxygen or even air under metal-free condition, as a promising catalytic approach, has received increasing attention and become the method of choice for the activation of C(sp<sup><strong>3</strong></sup>)-H bonds. This review introduced briefly the pioneering works and listed detailed updates of the methodology development, synthetic applications especially in the late-stage modification of drugs or natural products, and mechanism studies on photo-promoted aerobic C(sp<sup><strong>3</strong></sup>)-H oxidation/oxygenation by organic catalysts from 2020 to 2024. And this review is divided by the type of organic photocatalysts used in the C-H activation reactions. The production of oxygenated compounds, such as ketone, aldehyde, alcohol, hydroperoxide, and lactone has been accomplished by various of organic photocatalysts alone or the synergistic catalysis with a co-catalyst as the indirect hydrogen atom abstractor. The reaction scope, limitation, challenge, and future opportunities in this field have been discussed as well.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"174 ","pages":"Article 134496"},"PeriodicalIF":2.1,"publicationDate":"2025-01-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143342871","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-01-23DOI: 10.1016/j.tet.2025.134487
Zhen Yao , Ji Yang , Rong Huang , Chang Liu , Jing Guan , Ying Zhou , Xiongwei Liu , Bing Lin , Lijin Xu
A metal-free nucleophilic addition reaction of readily available 1,2-diaminobenzenes with α-ketoesters for synthesis of heterocyclic α,α-disubstituted-α-amino acids at room temperature under BF3·Et2O catalysis has been accomplished. This transformation occurs smoothly under mild conditions, providing easy access to various heterocyclic α,α-disubstituted-α-amino acids in 54–93 % yields with ample substrate scope, high compatibility of functional groups and easy scale-up. Choosing BF3·Et2O as Lewis acid is crucial for the success of this transformation.
{"title":"BF3-catalyzed nucleophilic addition reaction of 1,2-diaminobenzenes with α-ketoesters: Access to cyclic α,α-disubstituted α-amino acid derivatives","authors":"Zhen Yao , Ji Yang , Rong Huang , Chang Liu , Jing Guan , Ying Zhou , Xiongwei Liu , Bing Lin , Lijin Xu","doi":"10.1016/j.tet.2025.134487","DOIUrl":"10.1016/j.tet.2025.134487","url":null,"abstract":"<div><div>A metal-free nucleophilic addition reaction of readily available 1,2-diaminobenzenes with α-ketoesters for synthesis of heterocyclic α,α-disubstituted-α-amino acids at room temperature under BF<sub>3</sub>·Et<sub>2</sub>O catalysis has been accomplished. This transformation occurs smoothly under mild conditions, providing easy access to various heterocyclic α,α-disubstituted-α-amino acids in 54–93 % yields with ample substrate scope, high compatibility of functional groups and easy scale-up. Choosing BF<sub>3</sub>·Et<sub>2</sub>O as Lewis acid is crucial for the success of this transformation.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"174 ","pages":"Article 134487"},"PeriodicalIF":2.1,"publicationDate":"2025-01-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143343122","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Stagonosporyne G, a highly oxygenated cyclohexanoid isolated from the wheat pathogen Parastagonospora nodorum SN15, shows herbicidal activity against Arabidopsos thaliana and may contribute to the virulence of P. nodorum SN15 against wheat species. Herein, we report the first synthesis of stagonosporyne G from commercially available D-(−)-quinic acid via diastereoselective 1,4-addition of alkynylaluminum species, Rubottom oxidation, and Evans reduction of α-hydroxyenone as the key steps. The absolute configuration of the natural stagonosporyne G was confirmed by comparing the optical rotations of synthetic and natural compounds.
{"title":"Synthesis of stagonosporyne G from (−)-D-quinic acid","authors":"Kentaro Koyama, Hironori Okamura, Hirosato Takikawa","doi":"10.1016/j.tet.2025.134488","DOIUrl":"10.1016/j.tet.2025.134488","url":null,"abstract":"<div><div>Stagonosporyne G, a highly oxygenated cyclohexanoid isolated from the wheat pathogen <em>Parastagonospora nodorum</em> SN15, shows herbicidal activity against <em>Arabidopsos thaliana</em> and may contribute to the virulence of <em>P. nodorum</em> SN15 against wheat species. Herein, we report the first synthesis of stagonosporyne G from commercially available D-(−)-quinic acid via diastereoselective 1,4-addition of alkynylaluminum species, Rubottom oxidation, and Evans reduction of α-hydroxyenone as the key steps. The absolute configuration of the natural stagonosporyne G was confirmed by comparing the optical rotations of synthetic and natural compounds.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"173 ","pages":"Article 134488"},"PeriodicalIF":2.1,"publicationDate":"2025-01-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143356340","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Azetidine is a four-membered nitrogen-containing saturated heterocycle that has received significant attention in organic and medicinal chemistry research. Various FDA-approved drugs such as azelnidipine, cobimetinib, ximelagatran, and baricitinib contain azetidine moiety. The synthetic versatility of azetidine has been explored less due to its strained ring system. In the last decades, scientists have been working to advance their synthetic feasibility via greener routes. Thus, this review sheds light on the various green synthetic methodologies to achieve azetidine heterocycles, focusing on the high yield, stereoselective, and mild solvent/reaction medium. Importantly, an essential aspect of each synthetic strategy has been highlighted, which delves excellent insight into the desired transformation. Further, this review explores the versatile application of azetidine-based ligands in coupling reactions, asymmetric catalysis, and explosive materials. Besides, synthetic routes to FDA-approved azetidine-heterocycles have been reported, which commence the development of novel azetidine heterocycles with broader applications.
{"title":"Exploring azetidine containing heterocycles: From green synthesis to applications","authors":"Shivangi Jaiswal , Nikhilesh Arya , Dharma Kishore , Jaya Dwivedi , Swapnil Sharma","doi":"10.1016/j.tet.2025.134491","DOIUrl":"10.1016/j.tet.2025.134491","url":null,"abstract":"<div><div>Azetidine is a four-membered nitrogen-containing saturated heterocycle that has received significant attention in organic and medicinal chemistry research. Various FDA-approved drugs such as azelnidipine, cobimetinib, ximelagatran, and baricitinib contain azetidine moiety. The synthetic versatility of azetidine has been explored less due to its strained ring system. In the last decades, scientists have been working to advance their synthetic feasibility <em>via</em> greener routes. Thus, this review sheds light on the various green synthetic methodologies to achieve azetidine heterocycles, focusing on the high yield, stereoselective, and mild solvent/reaction medium. Importantly, an essential aspect of each synthetic strategy has been highlighted, which delves excellent insight into the desired transformation. Further, this review explores the versatile application of azetidine-based ligands in coupling reactions, asymmetric catalysis, and explosive materials. Besides, synthetic routes to FDA-approved azetidine-heterocycles have been reported, which commence the development of novel azetidine heterocycles with broader applications.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"174 ","pages":"Article 134491"},"PeriodicalIF":2.1,"publicationDate":"2025-01-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143342870","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-01-21DOI: 10.1016/j.tet.2025.134484
Kaimal Madhusoodhanan Neeraja , P. S. Devi , Gopinathan Anilkumar
Oxazoles are heterocyclic compounds distinguished by a five-membered ring structure, featuring oxygen and nitrogen atoms at positions one and three. Renowned for their diverse chemical and biological properties, oxazoles hold significant value across a spectrum of disciplines including medicinal chemistry, materials science, and agrochemicals. Their ubiquitous presence underscores their pivotal role in scientific research and industrial applications alike. In the initial phases, transition metal-mediated methodologies were commonly adopted for the synthesis of oxazoles. Frequent use of these metals can pose environmental and health risks, prompting efforts to develop sustainable and environmentally benign catalytic methodologies. Gold catalysis emerges as one of the preferred greener alternatives in this context. The straightforward, diverse, and extensive chemistry demonstrated by gold renders it a highly appealing option for catalysis. Driven by its remarkable versatility and distinctive properties, we have gathered here the progress made in gold-catalyzed oxazole synthesis since 2004. The key advantages of this reaction lie in its high efficiency, chemoselectivity, regioselectivity, recyclability of the catalytic system, greater atom economy, and mild reaction setup. This review provides an overview of the Au-catalyzed oxazole synthesis covering the literature until early 2024.
{"title":"Recent advances and prospects in the gold-catalyzed synthesis of oxazoles","authors":"Kaimal Madhusoodhanan Neeraja , P. S. Devi , Gopinathan Anilkumar","doi":"10.1016/j.tet.2025.134484","DOIUrl":"10.1016/j.tet.2025.134484","url":null,"abstract":"<div><div>Oxazoles are heterocyclic compounds distinguished by a five-membered ring structure, featuring oxygen and nitrogen atoms at positions one and three. Renowned for their diverse chemical and biological properties, oxazoles hold significant value across a spectrum of disciplines including medicinal chemistry, materials science, and agrochemicals. Their ubiquitous presence underscores their pivotal role in scientific research and industrial applications alike. In the initial phases, transition metal-mediated methodologies were commonly adopted for the synthesis of oxazoles. Frequent use of these metals can pose environmental and health risks, prompting efforts to develop sustainable and environmentally benign catalytic methodologies. Gold catalysis emerges as one of the preferred greener alternatives in this context. The straightforward, diverse, and extensive chemistry demonstrated by gold renders it a highly appealing option for catalysis. Driven by its remarkable versatility and distinctive properties, we have gathered here the progress made in gold-catalyzed oxazole synthesis since 2004. The key advantages of this reaction lie in its high efficiency, chemoselectivity, regioselectivity, recyclability of the catalytic system, greater atom economy, and mild reaction setup. This review provides an overview of the Au-catalyzed oxazole synthesis covering the literature until early 2024.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"174 ","pages":"Article 134484"},"PeriodicalIF":2.1,"publicationDate":"2025-01-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143342943","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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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