TetrahedronPub Date : 2025-03-11DOI: 10.1016/j.tet.2025.134587
Chunyu Li, Yujia Wang, Zhenjiang Li, Ling Li, Min Zhang, Yanqi Shi, Yue Xu, Xin Zou, Xin Yuan, Kai Guo
{"title":"Bidentate deltamide hydrogen bond donor catalyzed cycloaddition of carbon dioxide into epoxide","authors":"Chunyu Li, Yujia Wang, Zhenjiang Li, Ling Li, Min Zhang, Yanqi Shi, Yue Xu, Xin Zou, Xin Yuan, Kai Guo","doi":"10.1016/j.tet.2025.134587","DOIUrl":"10.1016/j.tet.2025.134587","url":null,"abstract":"<div><div>The cycloaddition of carbon dioxide into epoxides through hydrogen bond donor (HBD) and halide nucleophile as a binary catalyst to afford cyclic carbonates has become a key strategy for fixing carbon dioxide. A series of bidentate HBD catalysts of deltamides featured with N–H bond were synthesized and evaluated in the cycloaddition of CO<sub>2</sub> to epoxides (CCE) reactions. The influences on the catalytic activity were scrutinized, which included tunable substituents, types of nucleophiles, reaction time, temperature and the loading of the catalyst. The HBD catalyst 2,3-bis((4-(trifluoromethyl)phenyl)amino)cycloprop-2-en-1-one (DT3) with substituted –CF<sub>3</sub> group in combination with tetrabutylammonium iodide (NBu<sub>4</sub>I) showed the best performance with 95 % conversion of styrene oxide into cyclic carbonate under mild conditions (0.1 MPa, 100 °C and 12 h). Substrate applicability of the catalyst is illustrated by the conversion of quantity terminal epoxides with excellent yields and quantitative selectivity. <sup>1</sup>H NMR titration spectra and control studies were employed to probe a reasonable activation mechanism of the cycloaddition of CO<sub>2</sub> to epoxides reactions.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"177 ","pages":"Article 134587"},"PeriodicalIF":2.1,"publicationDate":"2025-03-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143628138","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}
TetrahedronPub Date : 2025-03-11DOI: 10.1016/j.tet.2025.134578
Xianhe Fang , Jiaxing Lv , Shuxin Yang , Mingyu Ma , Runzhe Yang , Yi Bi
{"title":"Cascade C(sp3)-H bond functionalization/cyclization reaction for the synthesis of 3,3-disubstituted oxindoles by decatungstate photocatalysis","authors":"Xianhe Fang , Jiaxing Lv , Shuxin Yang , Mingyu Ma , Runzhe Yang , Yi Bi","doi":"10.1016/j.tet.2025.134578","DOIUrl":"10.1016/j.tet.2025.134578","url":null,"abstract":"<div><div>Herein, we describe a cascade C(sp<sup>3</sup>)-H bond functionalization/cyclization reaction for the synthesis of 3,3-disubstituted oxindoles. The reaction is catalyzed by decatungstate anion under near-ultraviolet light irradiation. Functionalization of aliphatic C(sp<sup>3</sup>)−H bonds occurs efficiently through this catalytic reaction. Furthermore, the selected products exhibited inhibitory effects on LPS-induced macrophage nitric oxide release.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"177 ","pages":"Article 134578"},"PeriodicalIF":2.1,"publicationDate":"2025-03-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143609386","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}
{"title":"Isolation, characterization, and biological activities of halogenated sesquiterpenes and C15 acetogenins from the Okinawan sea hare, Aplysia argus","authors":"Ryunosuke Nakamura , Koushi Matsuyama , Naomichi Arima , Fumito Tani , Satoaki Onitsuka , Hiroaki Okamura , Tetsuo Iwagawa , Masayuki Sudoh , Toshiyuki Hamada","doi":"10.1016/j.tet.2025.134588","DOIUrl":"10.1016/j.tet.2025.134588","url":null,"abstract":"<div><div>The sea hare, scientifically known as <em>Aplysia argus</em>, is the focus of considerable research interest owing to its unique halogenated metabolites that may have vast potential in the fields of medicine and pharmaceuticals. This paper reports the isolation of a new laurane-type sesquiterpene, 10-bromoisolaurinsiol (<strong>1</strong>), and a new halogenated C<sub>15</sub> acetogenin (<strong>2</strong>), along with several known halogenated secondary metabolites from the sea hare <em>Aplysia argus</em>. Their structures and relative stereochemistries were established through comprehensive 1D and 2D NMR analyses. Fourteen compounds, some of which were novel, were evaluated for their cytotoxic effects against S1T cells (a cancer cell line derived from adult T-cell leukemia patients) and their potential as SARS-CoV-2 main protease inhibitors.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"178 ","pages":"Article 134588"},"PeriodicalIF":2.1,"publicationDate":"2025-03-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143644749","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}
{"title":"Gold nanoparticle-enhanced cross-linked porous organic polymer photocatalysts for visible light-driven oxidation of phenylboronic acid","authors":"Xin Liu, Jiaxi Cai, Qiaoya Wang, Haixia Song, Aizhao Pan, Mingyou Hu","doi":"10.1016/j.tet.2025.134585","DOIUrl":"10.1016/j.tet.2025.134585","url":null,"abstract":"<div><div>The utilisation of photosensitive cross-linked porous organic polymers doped with Au nanoparticles (NPs) (PDI-BT-5-Au) has proven successful as a remarkably effective photocatalyst for the aerobic oxidation of phenylboronic acid to phenol, utilising O<sub>2</sub> under mild conditions. Furthermore, this research underscores the promise of Au NPs-enhanced cross-linked porous organic polymers as proficient, recyclable heterogeneous photocatalysts for organic transformations.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"177 ","pages":"Article 134585"},"PeriodicalIF":2.1,"publicationDate":"2025-03-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143592525","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}
TetrahedronPub Date : 2025-03-10DOI: 10.1016/j.tet.2025.134584
Qian Wang , Yue Wang , Er-Qing Li
{"title":"Catalyst-free [2 + 1] annulations of conjugated dienes and sulfur Ylides: Synthesis of cyclopropane derivatives","authors":"Qian Wang , Yue Wang , Er-Qing Li","doi":"10.1016/j.tet.2025.134584","DOIUrl":"10.1016/j.tet.2025.134584","url":null,"abstract":"<div><div>In this work, we report the [2 + 1] cycloaddition reaction between electron-deficient conjugated dienes and sulfur ylides under catalyst-free and base-free conditions. The method provides an efficient pathway for constructing cyclopropane frameworks. This protocol exhibits excellent regioselectivity, good yields, and broad functional group tolerance. Furthermore, the potential applications of this approach are demonstrated through gram-scale reactions and further synthetic transformations.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"177 ","pages":"Article 134584"},"PeriodicalIF":2.1,"publicationDate":"2025-03-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143609387","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}
{"title":"Synthesis of new enaminone derivatives and studying the one-pot three-component reaction of anilines, triethyl orthoformate, and active methylene compounds using CeO2 nanoparticles as a catalyzing","authors":"Arezoo Sardashti-Birjandi, Ebrahim Mollashahi, Malek Taher Maghsoodlou","doi":"10.1016/j.tet.2025.134577","DOIUrl":"10.1016/j.tet.2025.134577","url":null,"abstract":"<div><div>In this study, the synthesis of new enaminone derivatives via a three-component reaction of active methylene compounds, triethyl orthoformate, and aniline derivatives, in the presence of cerium oxide nanoparticles as an active catalyst, under solvent-free conditions has been developed. Cerium oxide nanoparticles were prepared using the aqueous extract of <em>Salvadora persica</em> as a green and environmentally friendly method. The effect of different parameters including solvent, reaction temperature, catalyst type, and catalyst amount was studied to achieve optimized reaction conditions. Cerium oxide nanoparticles have shown a higher yield than other catalysts such as Fe<sub>2</sub>O<sub>3</sub>, lactic acid, NaOAc, ZnCl<sub>2</sub>, nano-MgO, and nano-ZnO. The enaminone derivatives were synthesized in high to excellent yields with this protocol.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"177 ","pages":"Article 134577"},"PeriodicalIF":2.1,"publicationDate":"2025-03-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143578151","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}
TetrahedronPub Date : 2025-03-05DOI: 10.1016/j.tet.2025.134545
Li-Jun Li, Xin-Yue Li, Jin Zhang, Hong Li, Qiang-Wei Fan, Yang Li
{"title":"Progress in trifluoromethylation reaction of olefins","authors":"Li-Jun Li, Xin-Yue Li, Jin Zhang, Hong Li, Qiang-Wei Fan, Yang Li","doi":"10.1016/j.tet.2025.134545","DOIUrl":"10.1016/j.tet.2025.134545","url":null,"abstract":"<div><div>The presence of trifluoromethyl in the drug molecule can effectively improve its lipophilicity, absorbability, and metabolic stability. Therefore, the introduction of trifluoromethyl in organic molecules has attracted widespread attention. In recent years, the trifluoromethylation of olefins has been developed rapidly. In this paper, various synthesis methods and reaction mechanisms of trifluoromethylated olefins in recent years are reviewed from the perspectives of transition metal (Cu, Fe, Pd, Ni) catalysis and photocatalysis and free radical reactions.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"177 ","pages":"Article 134545"},"PeriodicalIF":2.1,"publicationDate":"2025-03-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143629602","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}
TetrahedronPub Date : 2025-03-03DOI: 10.1016/j.tet.2025.134569
Ali Nasirpour, Zarrin Ghasemi
{"title":"Synthesis of benzimidazo[1,2-c]quinazolin-6(5H)-one derivatives via copper-mediated C–H isocyanatation of 2-arylbenzimidazoles","authors":"Ali Nasirpour, Zarrin Ghasemi","doi":"10.1016/j.tet.2025.134569","DOIUrl":"10.1016/j.tet.2025.134569","url":null,"abstract":"<div><div>An efficient protocol is disclosed for the synthesis of benzimidazo[1,2-<em>c</em>]quinazolin-6(5<em>H</em>)-ones utilizing an atom-economical C–H functionalization method. Copper-mediated isocyanatation of the aryl ring of the prepared 2-arylbenzimidazole derivatives, followed with intramolecular cyclization reaction resulted in the desired products. We diversified and purified the products without chromatography.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"177 ","pages":"Article 134569"},"PeriodicalIF":2.1,"publicationDate":"2025-03-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143552740","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}
TetrahedronPub Date : 2025-03-01DOI: 10.1016/j.tet.2025.134567
Xian-Fei Deng, Yan-Jun Chen, Li-Yu Yi, Ju Huang
{"title":"New NHC–Pd complexes bearing bulky steric hindrance: Synthesis and catalytic activity in the Heteroaryl–Heteroaryl Buchwald–Hartwig amination reaction","authors":"Xian-Fei Deng, Yan-Jun Chen, Li-Yu Yi, Ju Huang","doi":"10.1016/j.tet.2025.134567","DOIUrl":"10.1016/j.tet.2025.134567","url":null,"abstract":"<div><div>New bulky N-heterocyclic carbene (NHC) palladium complexes {[Pd-PEPPSI-IPr<sup>tBuDBB</sup>]} were synthesized and characterized. The catalytic activity of the palladium complexes was evaluated via the direct C–N arylation of N-heteroaryl amines with aryl chlorides in aerobic conditions at 100 °C. Under the optimal conditions, 2 mol% of the bulky palladium was found to be very efficient and produced the desired cross-coupling products in high yields.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"177 ","pages":"Article 134567"},"PeriodicalIF":2.1,"publicationDate":"2025-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143552742","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}
{"title":"Sonochemically synthesized copper chelate from expired streptomycin sulfate as a sustainable catalyst for green synthesis of 1,4-disubstituted triazoles in aqueous medium","authors":"Neetu Mev , Yachana Jain , Lalita Yadav , Priya Sharma , Madhu Agarwal , Ragini Gupta","doi":"10.1016/j.tet.2025.134564","DOIUrl":"10.1016/j.tet.2025.134564","url":null,"abstract":"<div><div>This research work introduces a pioneering strategy for harnessing the potential of expired streptomycin sulfate as its copper chelate to catalyze the synthesis of biologically important 1,4-disubstituted-1,2,3-triazoles efficiently. The efficacy of this catalyst is showcased by the sonochemical 1,3-dipolar cycloaddition process, yielding 1,4-disubstituted-1,2,3-triazoles at 40 °C using a promotor ligand <span>l</span>-phenylalanine within 30 min in >90 % yield in aqueous media with high purity. The biocompatible promoter ligand assists the STR Cu chelate to enhance the reaction rate by stabilizing the Cu(I) oxidation state and preventing its undesirable disproportionation, thus increasing the yield of the intended product. The synthesized catalyst demonstrates extensive substrate compatibility and works equally well with precursors containing both electron donating and withdrawing groups (<strong>4–25</strong>). Additionally, all the synthesized compounds, as well as the catalyst, have been duly characterized by the usual analytical and spectroscopic techniques. Furthermore, the catalyst could be reused up to four cycles without a significant reduction in its catalytic performance.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"177 ","pages":"Article 134564"},"PeriodicalIF":2.1,"publicationDate":"2025-02-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143534666","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}