IF 2.1 3区化学

Tetrahedron Pub Date : 2024-11-03 DOI: 10.1016/j.tet.2024.134358

Howard Díaz-Salazar, Carlos M. Ramírez-González, Miguel A. Rosas-Ortega, Susana Porcel

引用次数: 0

Transition-metal-free nucleophilic substitution of alkenyl boronic acids with propargylic mesylates sp3-carbon electrophiles 烯基硼酸与丙炔基甲磺酸酯 sp3 碳亲电体的无过渡金属亲核取代反应

IF 2.1 3区化学

Tetrahedron Pub Date : 2024-11-02 DOI: 10.1016/j.tet.2024.134353

Wenna Xie , Shiwen Liu , Bo Xu

引用次数: 0

Gold(III)-catalyzed regioselective synthesis of vinyl-substituted pyrazolo[1,4]-oxazepines via 7-exo-trig cyclization 金(III)催化的乙烯基取代的吡唑并[1,4]氮杂卓通过 7-exo-trig 环化的区域选择性合成

IF 2.1 3区化学

Tetrahedron Pub Date : 2024-11-02 DOI: 10.1016/j.tet.2024.134340

Ravinder Guduru , Mathangi Sandeep , Komalla Sunil , N.S.V.M. Rao Mangina , Perla Bharath Kumar , Balasubramanian Sridhar , Galla V. Karunakar

引用次数: 0

Recent progress in metal-catalyzed C(sp³)-P bond formation 金属催化 C(sp³)-P 键形成的最新进展

IF 2.1 3区化学

Tetrahedron Pub Date : 2024-11-01 DOI: 10.1016/j.tet.2024.134352

Jia-Lin Tu , Zhengjia Shen , Binbin Huang

{"title":"Recent progress in metal-catalyzed C(sp³)-P bond formation","authors":"Jia-Lin Tu , Zhengjia Shen , Binbin Huang","doi":"10.1016/j.tet.2024.134352","DOIUrl":"10.1016/j.tet.2024.134352","url":null,"abstract":"<div><div>The construction of C(sp³)-P bonds is of paramount importance in organic synthesis, catalysis, and materials science. Organophosphorus compounds containing C(sp³)-P bonds serve as pivotal structural motifs in ligands, pharmaceuticals, agrochemicals, and functional materials. While traditional methods for C(sp³)-P bond formation largely rely on nucleophilic substitution or coupling of reactive organometallic reagents, recent years have witnessed significant advancements in metal-catalyzed approaches. This review highlights the recent developments in C(sp³)-P bond formation enabled by metals including Cu, Fe, Bi, Pd, Ni, Ru, Rh, and Co, with particular emphasis on methodologies that activate simple C(sp³)-H bonds or utilize readily available chemical feedstocks. Key mechanistic paradigms, including photoredox/transition metal dual catalysis, metal-catalyzed radical processes, and photo-induced ligand-to-metal charge transfer (LMCT), are critically discussed. This review evaluates the mechanistic insights, applications, and limitations of these methodologies in the synthesis of organophosphorus compounds, and provides perspectives on future directions to promote further advancements in C(sp³)-P bond formation strategies.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":null,"pages":null},"PeriodicalIF":2.1,"publicationDate":"2024-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142592592","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}

引用次数: 0

Transition metal promoted Brook rearrangement and its related reactions 过渡金属促进布鲁克重排及其相关反应

IF 2.1 3区化学

Tetrahedron Pub Date : 2024-10-31 DOI: 10.1016/j.tet.2024.134351

Fazhou Yang, Jinbao Wang, Yujie Dong, Nianci Zhang, Cheng Zhang

引用次数: 0

Synthesis and properties of β-arylated triphyrins[2.1.1] by successive introduction of one to six aryl groups at the β-pyrrole carbons 通过在 β-吡咯碳原子上连续引入 1 至 6 个芳基，合成 β-芳基化三吡咯[2.1.1] 及其特性

IF 2.1 3区化学

Tetrahedron Pub Date : 2024-10-30 DOI: 10.1016/j.tet.2024.134349

Akrti Sharma, Mangalampalli Ravikanth

{"title":"Synthesis and properties of β-arylated triphyrins[2.1.1] by successive introduction of one to six aryl groups at the β-pyrrole carbons","authors":"Akrti Sharma, Mangalampalli Ravikanth","doi":"10.1016/j.tet.2024.134349","DOIUrl":"10.1016/j.tet.2024.134349","url":null,"abstract":"<div><div>The β-arylated meso-tetra(p-tolyl) triphyrins[2.1.1] containing two, three, and four p-fluorophenyl groups were synthesized by reacting appropriate β-bromo triphyrin[2.1.1] with p-fluorophenyl boronic acid in toluene/THF/H2O (1:1:1) at 80 οC for 8 h–12 h and their properties were compared with our previously reported β-arylated triphyrins[2.1.1] containing one and six p-fluorophenyl groups. The increase of the number of p-fluorophenyl groups at the β-pyrrole carbons induces steric hindrance at the periphery of triphyrin[2.1.1] that results in the alteration of electronic properties due to distortion in the macrocycle which is reflected in their structure, spectral and redox properties. The X-ray structure analysis revealed that β-di(p-fluorophenyl) meso-tetra(p-tolyl) triphyrin[2.1.1] was almost planar like meso-tetra(phenyl) triphyrin[2.1.1] whereas the β-hexa(p-fluorophenyl) meso-tetra(p-tolyl) triphyrin[2.1.1] was significantly distorted. The absorption spectra of β-arylated triphyrins[2.1.1] showed bathochromically shifted Soret and Q-bands with reduction in absorption coefficients and increase in the bandwidth compared to the β-unsubstituted meso-tetra(p-tolyl) triphyrin[2.1.1] and the maximum effects were noted for β-hexa(p-fluorophenyl) meso-tetra(p-tolyl) triphyrin[2.1.1]. The β-arylated meso-tetra(p-tolyl) triphyrins[2.1.1] are stable under electrochemical conditions and DFT/TD-DFT studies are in agreement with the experimental observations.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":null,"pages":null},"PeriodicalIF":2.1,"publicationDate":"2024-10-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142572173","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}

引用次数: 0

Heterogeneous synthesis of benzo[f]indole-4,9-diones derivatives using sulfonic resin and photocatalytic study 使用磺酸树脂异构合成苯并[f]吲哚-4,9-二酮衍生物及光催化研究

IF 2.1 3区化学

Tetrahedron Pub Date : 2024-10-29 DOI: 10.1016/j.tet.2024.134337

Salma E. Mora-Rodríguez , Selene Lagunas-Rivera , J. Merced Martínez-Rosales , Yolanda Alcaraz-Contreras , Jorge Alberto Mendoza-Pérez , Miguel A. Vázquez

引用次数: 0

Mechanochemical cyclization of push-pull enamines with propargyl alcohols 推拉烯胺与丙炔醇的机械化学环化反应

IF 2.1 3区化学

Tetrahedron Pub Date : 2024-10-29 DOI: 10.1016/j.tet.2024.134339

Srinivasarao Yaragorla, Megavath Vinod, Dandugula Sneha Latha

引用次数: 0

Design and synthesis of 3,5-disubstituted isoxazoles by Cu-mediated 1,3-dipolar cycloaddition and their in silico evaluation as potential GABAB receptor modulators 通过铜介导的 1,3-二极环加成法设计和合成 3,5-二取代的异噁唑，并将其作为潜在的 GABAB 受体调节剂进行硅学评估

IF 2.1 3区化学

Tetrahedron Pub Date : 2024-10-29 DOI: 10.1016/j.tet.2024.134336

Zuleyma Martínez-Campos , Francisco José Palacios-Can , Susana T. López-Cortina , Rodrigo Said Razo-Hernández , Mario Fernández-Zertuche

{"title":"Design and synthesis of 3,5-disubstituted isoxazoles by Cu-mediated 1,3-dipolar cycloaddition and their in silico evaluation as potential GABAB receptor modulators","authors":"Zuleyma Martínez-Campos , Francisco José Palacios-Can , Susana T. López-Cortina , Rodrigo Said Razo-Hernández , Mario Fernández-Zertuche","doi":"10.1016/j.tet.2024.134336","DOIUrl":"10.1016/j.tet.2024.134336","url":null,"abstract":"<div><div>In this work, we report the synthesis of three series of 3,5-disubstituted isoxazoles (4a-d, 5a-d and 6a-d), as analogues of the clinically important drug baclofen. The isoxazole ring systems were assembled through the key copper-catalyzed 1,3-dipolar cycloaddition reaction between a nitrile oxide (generated in situ from nitro compounds) and an alkyne. An X-ray crystallography study shows that the 1,3-dipolar cycloaddition reactions proceeded with very high regioselectively, leading exclusively to the formation of the 3,5-disubstituted regio isomers. Additionally, it was possible to obtain these compounds in enantiomerically pure form using SuperQuat-type chiral auxiliary. As suggested by our QSAR analysis and docking studies, these analogues have the potential to be biologically active as GABAB receptor modulators. Finally, the absorption, distribution, properties of metabolism and excretion (ADME) of the synthesized molecules was also determined by a computational approach. From this work we obtained five molecules ((S)-4d, (S)-5b, (S)-6b, (S)-6c and (S)-6d) as potential GABAB receptor agonists.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":null,"pages":null},"PeriodicalIF":2.1,"publicationDate":"2024-10-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142578730","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}

引用次数: 0

Photochemical generation of ketenes from phenanthrene-based cyclobutanones 菲基环丁酮光化学生成烯酮

IF 2.1 3区化学

Tetrahedron Pub Date : 2024-10-29 DOI: 10.1016/j.tet.2024.134344

Alexander D. Roth, Zhazira Koldasbay, Brett H. Ford, Khaidar Kairbek, Heejoon Ahn, Tarini S. Hardikar, Katherine M. Lane, Sarah M. Haynes, Dasan M. Thamattoor

引用次数: 0

Tetrahedron最新文献