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Selective Carbonyl Reduction in Unsaturated Esters and Aldehydes by Transfer Hydrogenation 不饱和酯和醛的转移加氢选择性羰基还原。
IF 2.9 3区 化学
Organometallics Pub Date : 2025-07-17 DOI: 10.1021/acs.organomet.5c00094
Víctor Martínez-Agramunt, Lucas H. R. Passos, Dmitry G. Gusev, Eduardo Peris and Eduardo N. dos Santos*, 
{"title":"Selective Carbonyl Reduction in Unsaturated Esters and Aldehydes by Transfer Hydrogenation","authors":"Víctor Martínez-Agramunt,&nbsp;Lucas H. R. Passos,&nbsp;Dmitry G. Gusev,&nbsp;Eduardo Peris and Eduardo N. dos Santos*,&nbsp;","doi":"10.1021/acs.organomet.5c00094","DOIUrl":"10.1021/acs.organomet.5c00094","url":null,"abstract":"<p >Catalytic transfer hydrogenation (TH) is an alternative to the industrially relevant hydrogenation of carbonyl compounds, dismissing the use of pressurized reactors. Herein, we compare ruthenium and osmium pincer complexes as catalysts for the selective carbonyl reduction of the renewable methyl 10-undecenoate, myrtenal, and cinnamaldehyde. Their selective carbonyl reduction is challenging because they also have a C–C double bond susceptible to reduction or isomerization. The osmium complexes, used for the first time in TH, showed considerably better activity and selectivity than the ruthenium ones. The reactions were carried out at temperatures as low as 35 °C at short reaction times, and a solvent screening demonstrated that anisole, which has a high sustainability score, is also the most efficient solvent for these reactions. Finally, renewable ethanol was employed as a sacrificial hydrogen source, circumventing the use of the usually high-carbon-footprint dihydrogen.</p>","PeriodicalId":56,"journal":{"name":"Organometallics","volume":"44 14","pages":"1538–1544"},"PeriodicalIF":2.9,"publicationDate":"2025-07-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC12309145/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144758749","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}
引用次数: 0
Ru(II)-Arene Complexes of Pyrazole-Based Acylthiourea for Anticancer Application against Ovarian Cancer Cell Lines: Effect of Arene, Halido, and Acylthiourea Ligands 吡唑基酰基硫脲的Ru(II)-芳烃配合物对卵巢癌细胞系的抗癌作用：芳烃、卤代和酰基硫脲配体的作用
IF 2.9 3区 化学
Organometallics Pub Date : 2025-07-16 DOI: 10.1021/acs.organomet.5c00096
Jayachandraprakasan Jayadharini, Srividya Swaminathan, Mohamed Subarkhan Mohamed Kasim, Nattamai Bhuvanesh and Ramasamy Karvembu*, 
{"title":"Ru(II)-Arene Complexes of Pyrazole-Based Acylthiourea for Anticancer Application against Ovarian Cancer Cell Lines: Effect of Arene, Halido, and Acylthiourea Ligands","authors":"Jayachandraprakasan Jayadharini,&nbsp;Srividya Swaminathan,&nbsp;Mohamed Subarkhan Mohamed Kasim,&nbsp;Nattamai Bhuvanesh and Ramasamy Karvembu*,&nbsp;","doi":"10.1021/acs.organomet.5c00096","DOIUrl":"https://doi.org/10.1021/acs.organomet.5c00096","url":null,"abstract":"<p >A series of acylthiourea ligands (L) with variations at the C-terminal (thiophenyl or methylene-thiophenyl) by incorporating an N-substituted pyrazole and their Ru(II)-arene complexes [(arene)Ru(L)(X)<sub>2</sub>] (arene = <i>p</i>-cymene/benzene; X = chlorido (Cl)/iodido (I)) were synthesized and characterized using UV–vis, FT-IR, <sup>1</sup>H NMR and <sup>13</sup>C NMR spectroscopy, HRMS, and single crystal X-ray diffraction. DFT studies provided optimized geometries and electronic structures of the complexes, and molecular docking was performed with B-cell lymphoma 2 (Bcl-2) protein and DNA to assess their binding interactions. <i>In vitro</i> cytotoxicity of the ligands and complexes was evaluated against ovarian cancer cell lines (A2780 and cisplatin-resistant A2780). Complexes <b>C3</b>, <b>C4</b>, and <b>C6</b> exhibited significant cytotoxic activity, with IC<sub>50</sub> values lower than those of the precursors and cisplatin. Further studies using AO/EB staining, Hoechst staining, JC-1 assay, and flow cytometry indicated that these complexes could exhibit enabled apoptosis through mitochondrial dysfunction. The studies proved that the introduction of a methylene group in the ligand or varying arene/halido had a significant influence over cytotoxicity. Notably, the benzene complexes showed enhanced anticancer activity compared to their <i>p</i>-cymene counterparts. The most active complex, <b>C3</b>, also oxidized GSH to GSSG, suggesting a mechanism involving oxidative stress induction.</p>","PeriodicalId":56,"journal":{"name":"Organometallics","volume":"44 14","pages":"1545–1557"},"PeriodicalIF":2.9,"publicationDate":"2025-07-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144806468","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
IF 2.5 3区 化学
Organometallics Pub Date : 2025-07-14
Tatyana S. Koptseva, Yana O. Kovalenko, Evgeny V. Baranov and Igor L. Fedushkin*, 
{"title":"","authors":"Tatyana S. Koptseva,&nbsp;Yana O. Kovalenko,&nbsp;Evgeny V. Baranov and Igor L. Fedushkin*,&nbsp;","doi":"","DOIUrl":"","url":null,"abstract":"","PeriodicalId":56,"journal":{"name":"Organometallics","volume":"44 13","pages":"XXX-XXX XXX-XXX"},"PeriodicalIF":2.5,"publicationDate":"2025-07-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.acs.org/doi/pdf/10.1021/acs.organomet.5c00156","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144613588","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}
引用次数: 0
IF 2.5 3区 化学
Organometallics Pub Date : 2025-07-14
{"title":"","authors":"","doi":"","DOIUrl":"","url":null,"abstract":"","PeriodicalId":56,"journal":{"name":"Organometallics","volume":"44 13","pages":"XXX-XXX XXX-XXX"},"PeriodicalIF":2.5,"publicationDate":"2025-07-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.acs.org/doi/pdf/10.1021/omv044i013_1958107","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144613592","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}
引用次数: 0
IF 2.5 3区 化学
Organometallics Pub Date : 2025-07-14
Darya O. Prima*,  and , Sergey Z. Vatsadze*, 
{"title":"","authors":"Darya O. Prima*,&nbsp; and ,&nbsp;Sergey Z. Vatsadze*,&nbsp;","doi":"","DOIUrl":"","url":null,"abstract":"","PeriodicalId":56,"journal":{"name":"Organometallics","volume":"44 13","pages":"XXX-XXX XXX-XXX"},"PeriodicalIF":2.5,"publicationDate":"2025-07-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.acs.org/doi/pdf/10.1021/acs.organomet.5c00117","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144613594","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}
引用次数: 0
Cationic Half-Sandwich Ruthenium(II) Complexes of 2-Picolyl-Based N-Arylguanidines as Catalysts for the Aldehyde–Water Shift Reaction 2-吡啶基n -芳基胍的阳离子半夹心钌（II）配合物催化醛-水转移反应
IF 2.9 3区 化学
Organometallics Pub Date : 2025-07-14 DOI: 10.1021/acs.organomet.5c00056
Harish Parihar, Pooja Yadav and Natesan Thirupathi*, 
{"title":"Cationic Half-Sandwich Ruthenium(II) Complexes of 2-Picolyl-Based N-Arylguanidines as Catalysts for the Aldehyde–Water Shift Reaction","authors":"Harish Parihar,&nbsp;Pooja Yadav and Natesan Thirupathi*,&nbsp;","doi":"10.1021/acs.organomet.5c00056","DOIUrl":"https://doi.org/10.1021/acs.organomet.5c00056","url":null,"abstract":"<p >The bridge-splitting reaction (bsr) of [η<sup>6</sup>-(<i>p</i>-cymene)Ru(μ-Cl)Cl]<sub>2</sub> with two equiv of guanidines <b>1</b>–<b>3</b> and <b>5</b>–<b>9</b> in toluene at RT afforded cationic complexes, [η<sup>6</sup>-(<i>p</i>-cymene)Ru(NN)Cl]Cl (<b>11</b>–<b>18</b>) in 80%–93% yields and the analogous reaction involving [η<sup>6</sup>-(<i>p</i>-cymene)Ru(μ-Cl)Cl]<sub>2</sub> and two equiv of guanidines <b>4</b> and <b>10</b> and the reaction involving [(η<sup>6</sup>-C<sub>6</sub>Me<sub>6</sub>)Ru(μ-Cl)Cl]<sub>2</sub> and two equiv of guanidines <b>3</b> and <b>9</b> afforded cationic complexes [η<sup>6</sup>-(<i>p</i>-cymene)Ru(NN)Cl]Cl (<b>19</b> and <b>20</b>) and [(η<sup>6</sup>-C<sub>6</sub>Me<sub>6</sub>)Ru(NN)Cl]Cl (<b>21</b> and <b>22</b>) in 83%–89% yields. The bsr reaction of [η<sup>6</sup>-(<i>p</i>-cymene)Ru(μ-Cl)Cl]<sub>2</sub> with guanidine <b>9</b> followed by an anion exchange reaction with NH<sub>4</sub>PF<sub>6</sub> in MeOH at RT afforded [η<sup>6</sup>-(<i>p</i>-cymene)Ru(NN)Cl]PF<sub>6</sub> (<b>23</b>) in 90% yield. Molecular structures of two guanidines and seven complexes were determined by SCXRD. Thirteen new complexes were screened as catalysts for the Aldehyde–Water Shift (AWS) reaction of 4-anisaldehyde at 0.1 mol % catalyst loading, and from the screening experiments, <b>18</b> turned out to be the best catalyst. The scope of a variety of substrates was explored and a plausible mechanism of AWS reaction is proposed. Some key reactions were carried out to strengthen the proposed mechanism of AWS reaction. This work represents the first practical, sustainable, and, in the case of cinnamaldehyde, a chemo-selective procedure for aryl carboxylic acids obtained through AWS reaction. The catalytic activity of <b>18</b> surpasses the catalytic activities of the known complexes reported in the literature.</p>","PeriodicalId":56,"journal":{"name":"Organometallics","volume":"44 14","pages":"1518–1529"},"PeriodicalIF":2.9,"publicationDate":"2025-07-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144806247","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
IF 2.5 3区 化学
Organometallics Pub Date : 2025-07-14
Kyle J. McGuire, Austin J. Ebarb, Prakhar Gautam and Tong Ren*, 
{"title":"","authors":"Kyle J. McGuire,&nbsp;Austin J. Ebarb,&nbsp;Prakhar Gautam and Tong Ren*,&nbsp;","doi":"","DOIUrl":"","url":null,"abstract":"","PeriodicalId":56,"journal":{"name":"Organometallics","volume":"44 13","pages":"XXX-XXX XXX-XXX"},"PeriodicalIF":2.5,"publicationDate":"2025-07-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.acs.org/doi/pdf/10.1021/acs.organomet.5c00097","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144613578","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}
引用次数: 0
IF 2.5 3区 化学
Organometallics Pub Date : 2025-07-14
Nondumiso L. Ngcobo, Thandeka A. Tshabalala, Stephen O. Ojwach* and Holliness Nose*, 
{"title":"","authors":"Nondumiso L. Ngcobo,&nbsp;Thandeka A. Tshabalala,&nbsp;Stephen O. Ojwach* and Holliness Nose*,&nbsp;","doi":"","DOIUrl":"","url":null,"abstract":"","PeriodicalId":56,"journal":{"name":"Organometallics","volume":"44 13","pages":"XXX-XXX XXX-XXX"},"PeriodicalIF":2.5,"publicationDate":"2025-07-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.acs.org/doi/pdf/10.1021/acs.organomet.5c00063","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144613590","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}
引用次数: 0
Flash Communication: Density Functional Theory (DFT) Calculations Indicate an Unconventional Anagostic Complex for the Initial Stage of the Reported Sc3+ Boosted C–H Bond Activation of 3,4-Dimethoxyacetanilide with Pd(OAc)2 闪烁通信：密度泛函理论（DFT）计算表明，在报道的Sc3+促进3,4-二甲氧基乙酰苯胺与Pd(OAc)2的C-H键激活的初始阶段，一个非常规的难解配合物
IF 2.9 3区 化学
Organometallics Pub Date : 2025-07-14 DOI: 10.1021/acs.organomet.5c00192
M. Arif Sajjad, Peter Schwerdtfeger, John A. Harrison* and Alastair J. Nielson*, 
{"title":"Flash Communication: Density Functional Theory (DFT) Calculations Indicate an Unconventional Anagostic Complex for the Initial Stage of the Reported Sc3+ Boosted C–H Bond Activation of 3,4-Dimethoxyacetanilide with Pd(OAc)2","authors":"M. Arif Sajjad,&nbsp;Peter Schwerdtfeger,&nbsp;John A. Harrison* and Alastair J. Nielson*,&nbsp;","doi":"10.1021/acs.organomet.5c00192","DOIUrl":"https://doi.org/10.1021/acs.organomet.5c00192","url":null,"abstract":"<p >Structural details for the complex [(3,4-dimethoxyacetanilide)(MeCN)Pd(OAc)<sub>2</sub>Sc(Otf)<sub>3</sub>] obtained from Density Functional Theory calculations indicate that with a three-atom tether coordination, the ligand aromatic ring lies in an above-plane position where steric constraints within the molecule give rise to a nonrotational anagostic-like complex where the C–H bond electron density does not penetrate the palladium core. Hirschfeld-based Independent Gradient Method partition and Natural Bond Orbital analyses confirm that there is no η<sup>2</sup>-π-donation or agostic interaction. When the MeCN ligand is removed from the complex, energy minimization results in the ring moving into the plane and an η<sup>1</sup>-σ-bonded complex results where weak agostic donation from an aromatic ring <i>ortho</i>-C–H bond occurs.</p>","PeriodicalId":56,"journal":{"name":"Organometallics","volume":"44 14","pages":"1505–1509"},"PeriodicalIF":2.9,"publicationDate":"2025-07-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144806219","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
IF 2.5 3区 化学
Organometallics Pub Date : 2025-07-14
Linyao Liu, Qianhang Wang, Yue Zhao, Bingjie Fu, Yue Long, Yang Li*, Wenfeng Jiang* and Wei Bai*, 
{"title":"","authors":"Linyao Liu,&nbsp;Qianhang Wang,&nbsp;Yue Zhao,&nbsp;Bingjie Fu,&nbsp;Yue Long,&nbsp;Yang Li*,&nbsp;Wenfeng Jiang* and Wei Bai*,&nbsp;","doi":"","DOIUrl":"","url":null,"abstract":"","PeriodicalId":56,"journal":{"name":"Organometallics","volume":"44 13","pages":"XXX-XXX XXX-XXX"},"PeriodicalIF":2.5,"publicationDate":"2025-07-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.acs.org/doi/pdf/10.1021/acs.organomet.5c00136","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144613595","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}
引用次数: 0
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