Journal of Organometallic Chemistry最新文献

{"title":"One-pot sustainable synthesis of novel pyrido[2,3-d]pyrimidinones and their evaluation for antitubercular and anticancer activity","authors":"Sumaiya Tabassum ,&nbsp;Sankar Ganesh Ramaraj ,&nbsp;J. Rajprasad ,&nbsp;Vivekananthan Sadaiyandi ,&nbsp;Niraj Kumar ,&nbsp;Santhosh Govindaraju","doi":"10.1016/j.jorganchem.2024.123450","DOIUrl":"10.1016/j.jorganchem.2024.123450","url":null,"abstract":"<div><div>A novel green protocol for the construction of diversified pyrido[2,3-<em>d</em>]pyrimidinones was accomplished by a single-pot reaction of aryl aldehydes, Meldrum's acid, thiobarbituric acid, and ammonium acetate/aniline in H₂O using ʟ-proline as an expeditious reusable catalyst at room temperature (26 °C). Our strategy provides an innovative synthetic avenue for the construction of pyrido[2,3-<em>d</em>]pyrimidinones, as well as several advantages over traditional methods, including a simple procedure, shorter reaction duration, excellent yields, safe handling, easy workup, catalyst recovery, and environmental compatibility. Furthermore, the synthesised compounds were tested for their impact on different cell lines and microorganisms. Compounds 5d and 5e were particularly effective against Mycobacterium tuberculosis (antitubercular), human breast cancer cells (MCF-7), lung cancer cells (A549 and NCI-H460), and both Gram-positive (S. pyogenes) and Gram-negative (E. coli) bacteria. The derivatives with hydroxyl and nitro substitutions [5e, 5f] showed the highest potency against MCF-7, A549, and NCI-H460 cell lines, with IC₅₀ values of 3.68–4.36, 3.82–3.41, and 11.34–12.28 µg/mL, respectively.</div></div>","PeriodicalId":374,"journal":{"name":"Journal of Organometallic Chemistry","volume":"1025 ","pages":"Article 123450"},"PeriodicalIF":2.1,"publicationDate":"2024-11-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142744019","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":"Catalytic epoxidation of olefin over metal-organic framework solids: A mini-review","authors":"Subratanath Koner","doi":"10.1016/j.jorganchem.2024.123449","DOIUrl":"10.1016/j.jorganchem.2024.123449","url":null,"abstract":"<div><div>By the turn of new millennium, especially last two decades witnessed an explosive growth of metal-organic framework (MOF) chemistry and studies on their functional properties. In the last few years, in particular, usage of metal-organic framework in heterogeneous catalysis have attracted a lot of attention. Catalytic research is mainly focused on the transition metal MOFs, however, of late, non-transition metal-based MOFs are also used. Here, epoxidation/oxidation reaction catalyzed by MOF under heterogeneous condition will be summarized. We have designed quite a few lanthanide metal-based MOFs that showed spectacular catalytic activity in oxidation/epoxidation. This mini-review will give a brief description of catalytic epoxidation over metal-organic frameworks along with research activity in our laboratory on this particular area.</div></div>","PeriodicalId":374,"journal":{"name":"Journal of Organometallic Chemistry","volume":"1025 ","pages":"Article 123449"},"PeriodicalIF":2.1,"publicationDate":"2024-11-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142744020","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":"Recent progress in synthesis, reactivity, and biological activities of selenopheno[2,3-c/3,2-c] pyrazole heterocycles","authors":"Moustafa A. Gouda ,&nbsp;Osama Alharbi ,&nbsp;Nahlah A. Al-Hadhrami ,&nbsp;Reem A.K. Alharbi ,&nbsp;Rasha Jame","doi":"10.1016/j.jorganchem.2024.123447","DOIUrl":"10.1016/j.jorganchem.2024.123447","url":null,"abstract":"<div><div>Pyrazole and selenophene are valuable heterocyclic compounds that play a crucial role in the development of new drug molecules. Combining the selenophene and pyrazole moieties to hybrid structures has opened exciting possibilities for various pharmacological activities, leading to the discovery of selenophenopyrazoles, including selenopheno[2,3-<em>c</em>]pyrazole and selenopheno[3,2-<em>c</em>]pyrazole. All of which exhibit intriguing properties. The synthesis of selenophenopyrazoles can be accomplished through several chemical reactions: Vilsmeier–Haack reaction, Thorpe–Ziegler cyclization, and Suzuki cross-coupling.</div></div>","PeriodicalId":374,"journal":{"name":"Journal of Organometallic Chemistry","volume":"1024 ","pages":"Article 123447"},"PeriodicalIF":2.1,"publicationDate":"2024-11-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142721819","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":"DFT study on the mechanism and structural aspects of iron(II)-catalyzed condensation of epichlorohydrin and CO2","authors":"Alejandro Yañez-Cabrera ,&nbsp;Mario Sánchez ,&nbsp;Berenice Sampayo-Andrade ,&nbsp;Maribel Arroyo-Carranza ,&nbsp;Armando Ramírez-Monroy","doi":"10.1016/j.jorganchem.2024.123446","DOIUrl":"10.1016/j.jorganchem.2024.123446","url":null,"abstract":"<div><div>In this work, the catalytic cycle for the epichlorohydrin/CO₂ condensation using the [η⁵-(C₅H₅)Fe(CO)(L)]X complexes where L = NH₂(CH₂)₂PPh₂ and X <em>=</em> I (<strong>1</strong>), Br (<strong>2</strong>), Cl (<strong>3</strong>), OTf (<strong>4</strong>) and X = Br and L = NMe₂(CH₂)₂PPh₂ (<strong>7</strong>), NH₂(CH₂)₃PPh₂ (<strong>8</strong>), Py(CH₂)PPh₂ (<strong>9</strong>) and Py(PPh₂) (<strong>10</strong>), was studied computationally using density functional theory (DFT) at the ωB97xD/def2-TZVP level of theory. A good correlation between the optimized structures of complexes <strong>1</strong>–<strong>4</strong> and their respective X-ray diffraction (XRD) structures (used as experimental parameter) was found. Thus, the theoretical model was validated to study all the structures in the present work. The most thermodynamically and kinetically favored path for complexes <strong>1</strong>–<strong>4</strong> and <strong>8</strong>, bearing acid hydrogens, operates outside of the coordination sphere as an <em>ionic</em> pathway where the ionic intermediates are stabilized through hydrogen bonds. Catalyst <strong>2</strong> showed the most favored energy profile among complexes <strong>1</strong>–<strong>4</strong> at room temperature and at 80 °C, which supports the previously reported experimental results. This first computational approach also explains the catalytic activity of complexes <strong>1, 3</strong> and <strong>4</strong>. The most thermodynamically and kinetically favored path for complexes <strong>7, 9</strong>, and <strong>10</strong> was the <em>covalent</em> pathway which works in the inner sphere, with a metal-alkoxide and a metal-carbonate as intermediates. Computationally, catalyst <strong>10</strong> was the most active catalyst in the entire study, showing a completely spontaneous energy profile at room temperature, being of great relevance to be investigated experimentally. Finally, the chiral <strong><em>R</em>-</strong> and <strong><em>S</em></strong><em>-</em>[η⁵-(C₅H₅)Fe(CO)(H(Me)N(CH₂)₂PPh₂)]Br isomers, computationally built and optimized from complex <strong>2</strong>, were found to be highly favored stable isomers, also attractive for experimental research.</div></div>","PeriodicalId":374,"journal":{"name":"Journal of Organometallic Chemistry","volume":"1024 ","pages":"Article 123446"},"PeriodicalIF":2.1,"publicationDate":"2024-11-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142702844","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":"2,3-diferrocenyl-(1-triphenylphosphoranylidene)ketene: Synthesis and interactions with O, C, N, S, Se nucleophiles, characterization and X-ray diffraction","authors":"Claudia O. Oliva-Colunga,&nbsp;Jessica J. Sánchez García,&nbsp;Edgar A. Aguilar-Ortiz,&nbsp;Marcos Flores-Alamo,&nbsp;Lena Ruiz-Azuara,&nbsp;Elena I. Klimova","doi":"10.1016/j.jorganchem.2024.123441","DOIUrl":"10.1016/j.jorganchem.2024.123441","url":null,"abstract":"<div><div>The opening of the ring of 2,3-diferrocenylcyclopropenone <strong>1</strong> with triphenylphosphine was studied to obtain 2,3-diferrocenyl-(3-triphenylphosphoranylidene) ketene <strong>3</strong>. This was subsequently electrophile activated to react with different nucleophiles (<strong>O, C, N, S, Se</strong>) to obtain α,β-unsaturated carbonyl compounds with a preferable selectivity (<em>E</em>), which were stable under environmental conditions. The reduction reaction of the double bond of the α,β-unsaturated carbonyl compound was studied in the presence of hydrogen iodide. The structures of the synthesized compounds were established on the basis of data obtained from ¹H and ¹³C NMR spectroscopy and further confirmed by X-ray diffraction analysis.</div></div>","PeriodicalId":374,"journal":{"name":"Journal of Organometallic Chemistry","volume":"1024 ","pages":"Article 123441"},"PeriodicalIF":2.1,"publicationDate":"2024-11-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142703158","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":"Recyclable and reusable Pd(acac)2/BrettPhos/PEG-1000 system for the Suzuki-Miyaura coupling of nitroarenes","authors":"Qian Ye,&nbsp;Rong Liu,&nbsp;Li Wei,&nbsp;Mingzhong Cai","doi":"10.1016/j.jorganchem.2024.123442","DOIUrl":"10.1016/j.jorganchem.2024.123442","url":null,"abstract":"<div><div>Pd(acac)₂/BrettPhos in user-friendly polyethylene glycol (PEG-1000) is shown to be a highly efficient catalytic system for the Suzuki-Miyaura coupling of nitroarenes with arylboronic acids. The reaction proceeds smoothly at 130 °C with K₃PO₄·<em>n</em>H₂O as base without the use of 18-crown-6 as an additive, yielding a variety of functionalized unsymmetrical biaryls in good to high yields. The isolation of the products is facilely performed by the extraction with cyclohexane and more importantly, both expensive Pd(acac)₂ and BrettPhos in PEG-1000 system can be readily recycled and reused more than six times without a significant loss of catalytic efficiency.</div></div>","PeriodicalId":374,"journal":{"name":"Journal of Organometallic Chemistry","volume":"1024 ","pages":"Article 123442"},"PeriodicalIF":2.1,"publicationDate":"2024-11-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142703156","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":"Deep-red or near-infrared-emitting Iridium (III) complex as efficient phosphorescent dye for live cell imaging through staining in cytoplasm","authors":"Sicheng Yao ,&nbsp;Yan Zhang ,&nbsp;Xinying Liu ,&nbsp;Xinyu Dong,&nbsp;Zhiming Zhang,&nbsp;Xingqiang Lü,&nbsp;Guorui Fu","doi":"10.1016/j.jorganchem.2024.123443","DOIUrl":"10.1016/j.jorganchem.2024.123443","url":null,"abstract":"<div><div>Despite the bioimaging highly realized from Ir(III)-complexes with visible-light, the staining on organelles by NIR-emissive (NIR = near infrared) Ir(III)-complex species especially in cytoplasm was rarely reported. In this work, two new cationic iridium (III) complexes ({[Ir(C^N)₂(N^N)]⁺ ·(PF₆)⁻}; C^<em>N</em> = 2,3-diphenylquinoxaline (<strong>dpqx</strong>)⁻ or 1-(benzo[b]-thiophen-2-yl)-isoquinoline (<strong>iqbt</strong>)⁻; N^<em>N</em> = 2-(pyridin-2-yl)-5-(4-vinylphenyl)pyridine (4vp-2,2′-bpy)), namely {[Ir(dpqx)₂(4vp-2,2′-bpy)]⁺ ·(PF₆)⁻} (<strong>1</strong>) and {[Ir(iqbt)₂(4vp-2,2′-bpy)]⁺ ·(PF₆)⁻} (<strong>2</strong>) with efficient deep-red (<span><math><msubsup><mi>λ</mi><mrow><mtext>em</mtext></mrow><mtext>Max</mtext></msubsup></math></span> = 630 nm, Φ_PL = 0.19) and NIR-emissions (<span><math><msubsup><mi>λ</mi><mrow><mtext>em</mtext></mrow><mtext>Max</mtext></msubsup></math></span> = 683 nm, Φ_PL = 0.16), are obtained, respectively. Moreover, beneficial from the excellent biocompatibility and low cytotoxicity, each of the two cationic iridium (III) complexes <strong>1</strong> and <strong>2</strong>, enables to exclusively stain in the cytoplasm of live cells. This research might provide two ideal candidates in the design of high-efficiency deep-red or NIR emitting cationic iridium (III) complexes for specific bioimaging agents.</div></div>","PeriodicalId":374,"journal":{"name":"Journal of Organometallic Chemistry","volume":"1024 ","pages":"Article 123443"},"PeriodicalIF":2.1,"publicationDate":"2024-11-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142703157","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":"Recent advances on Pd schiff base catalysts in suzuki-miyaura cross-coupling reaction: A review","authors":"Iman Hussein Hasan ,&nbsp;Raed Muslim Mhaibes ,&nbsp;Abdul Amir H. Kadhum ,&nbsp;Hussein Ali Al-Bahrani ,&nbsp;Ali Thoulfikar A. Imeer ,&nbsp;Nihad A.M Al-Rashedi ,&nbsp;Guang Shu","doi":"10.1016/j.jorganchem.2024.123444","DOIUrl":"10.1016/j.jorganchem.2024.123444","url":null,"abstract":"<div><div>Carbon-carbon cross-coupling organic transformations are crucial in organic chemistry, but achieving them without a catalyst is challenging. Various catalysts based on complex have been developed to facilitate these reactions. Firstly, ligands based on phosphine were used, but their sensitive nature and toxic led researchers to turn to ligands based on Schiff base. These ligands are stable, simple to synthesize, and produce a variety of transition metal complexes. Ligands based on Schiff base are typically synthesized from the condensation reaction between carbonyl compounds and an amino group, and their complexes along with transition metal are widely used in different carbon–carbon cross-coupling organic transformations. In particular, palladium complexes, are well-known catalytic systems in carbon-carbon cross-coupling organic transformations such as the Suzuki-Miyaura cross-coupling organic transformations. This review focuses on the application of Pd Schiff base ligands in Suzuki-Miyaura reaction.</div></div>","PeriodicalId":374,"journal":{"name":"Journal of Organometallic Chemistry","volume":"1024 ","pages":"Article 123444"},"PeriodicalIF":2.1,"publicationDate":"2024-11-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142703155","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":"Recent advances in homogeneous catalysts for the acceptorless dehydrogenation of alcohols to ketones and aldehydes","authors":"Dhrubajit Borah ,&nbsp;Abhilash Sharma ,&nbsp;Rekha Rani Dutta ,&nbsp;Indrani Bhuyan ,&nbsp;Rupjyoti Dutta","doi":"10.1016/j.jorganchem.2024.123445","DOIUrl":"10.1016/j.jorganchem.2024.123445","url":null,"abstract":"<div><div>Oxidant-free oxidation, also known as acceptorless dehydrogenation, has emerged as a powerful strategy for the oxidation of alcohols. Besides yielding carbonyl compounds, the method produces hydrogen gas- a promising green fuel with water as the only by-product. The elimination of toxic and stoichiometric oxidants or hydrogen acceptors makes this approach attractive from the standpoint of green and sustainable chemistry. Consequently, several transition metals-based catalytic methods have been developed to synthesise ketones and aldehydes through this green method. In this review, we would like to summarise the recent development of homogeneous catalysts for the acceptorless dehydrogenation of primary and secondary alcohols to yield aldehydes and ketones, respectively. Also, we delve into the specific roles played by various ligands, including bi-functional ligands, in fine-tuning the stereo-electronic properties of the metal catalyst and delineate their impact on reaction outcomes.</div></div>","PeriodicalId":374,"journal":{"name":"Journal of Organometallic Chemistry","volume":"1024 ","pages":"Article 123445"},"PeriodicalIF":2.1,"publicationDate":"2024-11-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142703154","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":"Direct CO2 hydrogenation over Na and CeO2-promoted Iron and Cobalt-based Catalysts Supported on MCM-41","authors":"Aryane A. Marciniak ,&nbsp;Antonio E.C. Santos ,&nbsp;Hugo C. Reis ,&nbsp;Evelyn C.S. Santos ,&nbsp;Claudio J.A. Mota","doi":"10.1016/j.jorganchem.2024.123440","DOIUrl":"10.1016/j.jorganchem.2024.123440","url":null,"abstract":"<div><div>This contribution has studied iron or cobalt-based Fischer-Tropsch catalysts, promoted with CeO₂ and Na and supported on MCM-41 mesoporous silica in the direct CO₂ hydrogenation to hydrocarbons. The cobalt-based catalyst is more active in the presence of ceria as a promoter, presenting long-chain hydrocarbons under reaction conditions of 350 °C, 40 bar, H₂/CO₂ = 3, and GHSV = 6000 mL g^-1 h^-1. The characterization of the catalysts suggests that CoCeNa/M exhibits a strong Co-O-Si bond formation, preventing the cobalt oxide reduction to Co²⁺ species, which can be associated with methane production. On the other hand, iron-based catalysts present higher CO and CH₄ concentrations, as shown via in situ DRIFTS, suggesting a possible iron carbide phase, which can be formed by the severe FTS reaction conditions, producing a high concentration of water and competing with Sabatier reaction.</div></div>","PeriodicalId":374,"journal":{"name":"Journal of Organometallic Chemistry","volume":"1023 ","pages":"Article 123440"},"PeriodicalIF":2.1,"publicationDate":"2024-11-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142652595","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}