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Mechanisms and Site Selectivity of (Het)Ar–X Oxidative Addition to Pd(0) Are Controlled by Frontier Molecular Orbital Symmetry (Het)Ar-X与Pd(0)氧化加成的机理和位点选择性受前沿分子轨道对称性的控制
IF 2.5 3区 化学 Q2 CHEMISTRY, INORGANIC & NUCLEAR Pub Date : 2024-07-16 DOI: 10.1021/acs.organomet.4c00224
Jingru Lu, N. Schley, I. Paci, D. Leitch
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引用次数: 0
Mechanochemical Cascade Synthesis of Zinc Complexes for Catalytic C–S Coupling in One-Pot 一锅催化 C-S 偶联锌配合物的机械化学级联合成
IF 2.8 3区 化学 Q2 CHEMISTRY, INORGANIC & NUCLEAR Pub Date : 2024-07-13 DOI: 10.1021/acs.organomet.4c00200
Daming Feng, Xiujia Hao, Zhenduo Fei, Peng Huang, Fang Guo
The mechanochemical approach to transition metal catalysis offers a number of advantages, including a reduction in solvent usage and an acceleration of reaction times. This study elucidates a one-pot, two-step cascade catalytic synthesis enabled by mechanochemistry, which integrates the synthesis of bidentate zinc complexes and their application in carbon–sulfur coupling reactions. The zinc complexes were systematically modified by altering the halogen atoms attached to the metal center, utilizing the reduced Schiff base ligand N,N’-diphenylethylenediamine, which significantly influenced the catalytic efficiency. Under optimal conditions, a wide range of thioether products were synthesized, demonstrating broad applicability across various substrates. The mechanistic insights were enhanced through the execution of free radical trapping experiments and analysis of reaction intermediates, revealing an SN2 substitution mechanism in the formation of carbon–sulfur bond. Furthermore, the methodology adheres to green chemistry principles, as evidenced by the favorable green chemistry metrics obtained, indicating a sustainable and eco-friendly protocol for practical use.
过渡金属催化的机械化学方法具有许多优点,包括减少溶剂用量和加快反应时间。本研究阐明了一种由机械化学实现的一锅两步级联催化合成方法,该方法综合了双齿锌配合物的合成及其在碳硫偶联反应中的应用。利用还原型希夫碱配体 N,N'-二苯基乙二胺,通过改变连接到金属中心的卤素原子对锌配合物进行了系统修饰,从而显著影响了催化效率。在最佳条件下,合成了多种硫醚产物,证明了该催化剂对各种底物的广泛适用性。通过自由基捕获实验和反应中间产物分析,进一步加深了对机理的认识,揭示了碳硫键形成的 SN2 取代机理。此外,该方法坚持绿色化学原则,所获得的绿色化学指标也证明了这一点,表明这是一种可持续的、生态友好的实用方案。
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引用次数: 0
Ni(3,5-CF3stb)2(Et2O): A “Super-Naked” Nickel Complex Ni(3,5-CF3stb)2(Et2O):超裸 "镍络合物
IF 2.8 3区 化学 Q2 CHEMISTRY, INORGANIC & NUCLEAR Pub Date : 2024-07-11 DOI: 10.1021/acs.organomet.4c00213
Rakan Saeb, Nils Nöthling, Josep Cornella
Here, we report how the reduction of Ni(acac)2 in the presence of an electron-deficient stilbene (3,5-CF3stb (stb = trans-stilbene)) results in the formation of a heteroleptic 16-electron bis-(stilbene)Ni(0) complex supported by a labile Et2O ligand. The complex is highly reactive toward ligand exchange with even weakly coordinating species like arenes. While its reactivity in ethereal solvents is analogous to that of other tris-(stilbene)Ni(0), the ability to undergo ligand exchange with aromatic solvents permits access to currently inaccessible (stilbene)(η6-arene)Ni(0) complexes.
在这里,我们报告了在缺电子的二苯乙烯(3,5-CF3stb(stb = 反式二苯乙烯))存在下还原 Ni(acac)2,如何形成由易变 Et2O 配体支持的异极 16 电子双(二苯乙烯)Ni(0) 复合物。该配合物在与配体交换时具有很高的反应活性,甚至可以与烷等弱配位物种交换。它在乙醚溶剂中的反应性与其他三-(二苯乙烯)Ni(0) 类似,而与芳香溶剂进行配体交换的能力则允许获得目前无法获得的 (二苯乙烯)(η6-烯烃)Ni(0) 复合物。
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引用次数: 0
Exploration of Pynaphthyridine and Binaphthyridine Manganese(I) Tricarbonyl Complexes: Influence on Carbon Dioxide Reduction Electrocatalysis 萘啶和双萘啶三羰基锰(I)配合物的探索:对二氧化碳还原电催化的影响
IF 2.8 3区 化学 Q2 CHEMISTRY, INORGANIC & NUCLEAR Pub Date : 2024-07-11 DOI: 10.1021/acs.organomet.4c00008
Kailyn Y. Cohen, Hovnan Simonyan, Mason Ortiz, Benjamin F. Solomon, Luke Simkins, Raymond N. Dominey, Emma W. Goldman, Andrew B. Bocarsly
For CO2 electrocatalysts of the form fac-[Mn(diimine)(CO)3Br], we previously reported that expanding the π-system of the chelating ligand from 2,2′-bipyridine (bpy) to 2-(2-pyridyl)quinoline (pq) to 2,2′-biquinoline (bqn) introduced a shift in the mechanism for CO2 reduction to CO. Here, we have synthesized pynaphthyridine and binaphthyridine ligands which incorporate extra nitrogen atoms that can act as H-bond acceptors. Though these ligands redshift the MLCT bands, which has previously been associated with a decrease in electrocatalytic performance for CO2 reduction, MnBr(1,8-pynap) in acetonitrile (MeCN) displays a smaller overpotential for CO2 reduction than MnBr(pq). This effect was not observed in N,N-dimethylformamide (DMF), suggesting that H-bonding plays a major role in increasing the catalytic activity. While MnBr(1,8-bn) also had a higher Faradaic efficiency for CO formation than MnBr(bqn), it was not more effective than MnBr(1,8-pynap) in DMF. To demonstrate the importance of the nitrogen ring positions, MnBr(1,6-pynap) was also synthesized, where the aryl nitrogen is facing away from the Mn center. The MnBr(1,6-pynap) was a poor electrocatalyst for CO2 reduction, suggesting that the nonligated N atom in the 1,8-complexes stabilizes the Mn–C(O)OH intermediate.
对于面-[Mn(二亚胺)(CO)3Br]形式的 CO2 电催化剂,我们以前曾报道过,将螯合配体的 π 系统从 2,2′-联吡啶 (bpy) 扩展到 2-(2-吡啶基)喹啉 (pq) 再扩展到 2,2′-联喹啉 (bqn),会导致 CO2 还原成 CO 的机理发生转变。在这里,我们合成了萘啶和双萘啶配体,它们含有额外的氮原子,可以作为氢键受体。虽然这些配体会使 MLCT 波段发生重移,这与二氧化碳还原电催化性能下降有关,但在乙腈(MeCN)中,MnBr(1,8-pynap) 的二氧化碳还原过电势小于 MnBr(pq)。在 N,N-二甲基甲酰胺(DMF)中没有观察到这种效应,这表明氢键在提高催化活性方面发挥了重要作用。虽然 MnBr(1,8-bn)生成 CO 的法拉第效率也比 MnBr(bqn)高,但在 DMF 中并不比 MnBr(1,8-炔基)更有效。为了证明氮环位置的重要性,我们还合成了 MnBr(1,6-炔基),其中芳基氮远离锰中心。MnBr(1,6-pynap) 对二氧化碳还原的电催化作用很差,这表明 1,8 复合物中的非ligated N 原子稳定了 Mn-C(O)OH 中间体。
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引用次数: 0
Synthesis of a Cationic Cobalt–Selenolate Complex for Cooperative Sn–H Bond Activation: Solvent-Dependent Stereoselectivity in Alkyne Hydrostannylation 用于 Sn-H 键协同活化的阳离子钴-硒酸盐配合物的合成:炔烃氢化苯甲酰基反应中溶剂依赖的立体选择性
IF 2.8 3区 化学 Q2 CHEMISTRY, INORGANIC & NUCLEAR Pub Date : 2024-07-11 DOI: 10.1021/acs.organomet.4c00236
Saravanakumar Elangovan, Tobias Randt, Elisabeth Irran, Hendrik F. T. Klare, Martin Oestreich
The preparation and structural characterization of a novel cationic cobalt(III) selenolate complex of type [Cp*Co(PySe)]22 + 2[BArF4] (Cp* = pentamethylcyclopentadienyl, PySe = pyridine-2-selenolate, ArF = 3,5-bis(trifluoromethyl)phenyl) is described. The synthesis is achieved by iodide abstraction from the neutral precursor [Cp*Co(PySe)I], which is readily accessible from [Cp*Co(CO)I2] and 2,2′-dipyridyl diselenide. The selenium-bridged dicationic dimer facilitates the cooperative heterolytic Sn–H bond activation of tributyltin hydride, as elucidated by multinuclear NMR spectroscopy. The potential of this air-stable cobalt(III) selenolate complex to function as a precatalyst for the catalytic hydrostannylation of phenylacetylene at ambient temperature is also demonstrated. Depending on the solvent, either cis- or trans-addition of nBu3SnH is observed, providing access to the E- and Z-vinylstannane, respectively.
本文介绍了一种新型阳离子硒酸钴(III)络合物 [Cp*Co(PySe)]22 + 2[BArF4]- 的制备方法和结构特征(Cp* = 五甲基环戊二烯,PySe = 吡啶-2-硒酸锂,ArF = 3,5-双(三氟甲基)苯基)。合成是通过从中性前体[Cp*Co(PySe)I]中抽取碘化物实现的,而[Cp*Co(CO)I2]和 2,2′-二吡啶基二硒化物很容易获得中性前体[Cp*Co(PySe)I]。正如多核核磁共振光谱所阐明的那样,硒桥接的二阳离子二聚体促进了三丁基氢化锡 Sn-H 键的合作异溶性活化。此外,还证明了这种空气稳定的硒酸钴(III)配合物在常温下作为催化苯乙炔氢化的前催化剂的潜力。根据溶剂的不同,可以观察到 nBu3SnH 的顺式或反式加成,从而分别获得 E-和 Z-乙烯基锡烷。
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引用次数: 0
Diverted Telomerization Reaction with Aryl Boronic Derivatives: Expeditious Synthesis of Aryl-Substituted 1,6- and 1,7-dienes 芳基硼酸衍生物的转移端粒化反应:快速合成芳基取代的 1,6- 和 1,7- 二烯
IF 2.8 3区 化学 Q2 CHEMISTRY, INORGANIC & NUCLEAR Pub Date : 2024-07-10 DOI: 10.1021/acs.organomet.4c00203
Belén Lerma-Berlanga, José Pedro Cerón-Carrasco, Antonio Leyva-Pérez
The telomerization reaction is a fundamental transformation in industry for the synthesis of highly substituted medium linear carbon chain products (8–12 carbon atoms) with heteroatoms (typically oxygen and nitrogen atoms). Here we show that this multibond forming reaction can be interrupted by adding an aryl boronic derivative in the reaction mixture, which diverts the reaction pathway from the final heteroatom toward the aryl coupling to give aryl-substituted 1,6- and 1,7-dienes in a very simple manner. Carbon chains between 14 and 30 carbon atoms can be prepared. Experimental and computational studies support a reaction mechanism that combines the classical telomerization reaction during the first steps and the Tsuji–Trost reaction for the last steps. These results open the way to designing different telomerization reactions where the final coupled fragment is not a canonical nucleophile.
端粒化反应是工业中合成带有杂原子(通常是氧原子和氮原子)的高取代中线性碳链产品(8-12 个碳原子)的基本转化过程。在这里,我们展示了通过在反应混合物中加入芳基硼酸衍生物可以中断这种多键形成反应,从而使反应路径从最后的杂原子转向芳基偶联,以非常简单的方式得到芳基取代的 1,6- 和 1,7- 二烯。可以制备出 14 至 30 个碳原子的碳链。实验和计算研究支持这样一种反应机理:在前几个步骤中结合经典的端粒化反应,在最后几个步骤中结合辻-特罗斯特反应。这些结果为设计不同的端粒化反应开辟了道路,在这些反应中,最终的偶联片段不是典型的亲核体。
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引用次数: 0
Theoretical Studies on Relative Stability of Cationic 1,10-Phenanthroline Palladium Complexes Bearing Alkyl Groups by Using Designed Alkane Templates 利用设计的烷烃模板对含烷基的阳离子 1,10-菲罗啉钯配合物相对稳定性的理论研究
IF 2.8 3区 化学 Q2 CHEMISTRY, INORGANIC & NUCLEAR Pub Date : 2024-07-09 DOI: 10.1021/acs.organomet.4c00097
Kazuma Muto, Miho Hatanaka, Fumitoshi Kakiuchi, Takuya Kochi
Density functional theory (DFT) calculations were conducted by using designed alkane templates, 2-methylpentane and 2-methylhexanes, which allowed for effective comparison of relative stabilities of alkylpalladium complexes with various numbers of branches at the α-carbon and the agostic β-carbon. The calculation results suggested that the alkylpalladium complexes bearing a 1,10-phenanthroline ligand are more stabilized when they have more branches at the α-carbon. In addition, the complexes with an agostic β-C(2°)–H or β-C(3°)–H bond generally have Gibbs free energies lower than those with an agostic β-C(1°)–H bond.
利用设计的烷烃模板(2-甲基戊烷和 2-甲基己烷)进行了密度泛函理论(DFT)计算,从而有效地比较了烷基钯配合物在 α 碳和同位 β 碳上具有不同数量分支的相对稳定性。计算结果表明,当烷基钯络合物中 1,10-菲罗啉配体的α-碳分支较多时,烷基钯络合物会更加稳定。此外,具有β-C(2°)-H或β-C(3°)-H键的络合物的吉布斯自由能一般低于具有β-C(1°)-H键的络合物。
{"title":"Theoretical Studies on Relative Stability of Cationic 1,10-Phenanthroline Palladium Complexes Bearing Alkyl Groups by Using Designed Alkane Templates","authors":"Kazuma Muto, Miho Hatanaka, Fumitoshi Kakiuchi, Takuya Kochi","doi":"10.1021/acs.organomet.4c00097","DOIUrl":"https://doi.org/10.1021/acs.organomet.4c00097","url":null,"abstract":"Density functional theory (DFT) calculations were conducted by using designed alkane templates, 2-methylpentane and 2-methylhexanes, which allowed for effective comparison of relative stabilities of alkylpalladium complexes with various numbers of branches at the α-carbon and the agostic β-carbon. The calculation results suggested that the alkylpalladium complexes bearing a 1,10-phenanthroline ligand are more stabilized when they have more branches at the α-carbon. In addition, the complexes with an agostic β-C(2°)–H or β-C(3°)–H bond generally have Gibbs free energies lower than those with an agostic β-C(1°)–H bond.","PeriodicalId":56,"journal":{"name":"Organometallics","volume":null,"pages":null},"PeriodicalIF":2.8,"publicationDate":"2024-07-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141586721","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
Diamidoamine Aluminum Complex as Effective Initiator for Random Copolymerization of Substituted Carbonate with L-Lactide 二氨基胺铝络合物作为取代碳酸酯与 L-内酯无规共聚的有效引发剂
IF 2.8 3区 化学 Q2 CHEMISTRY, INORGANIC & NUCLEAR Pub Date : 2024-07-09 DOI: 10.1021/acs.organomet.4c00078
Milana U. Agaeva, Vladislav I. Filippenko, Badma N. Mankaev, Valeriia A. Serova, Konstantin A. Lyssenko, Elena V. Chernikova, Mikhail P. Egorov, Sergey S. Karlov
Designing a catalyst for random copolymerization by ring-opening polymerization (ROP) is an actual task. In the present work, we report the synthesis of aluminum complexes (R′ = Et, R′′ = Ph (5); R′ = Bn, R′′ = Ph (6); R′ = t-Bu, R′′ = Ph (7); R′ = R′′ = Ph (8)] based on diamidoamine pro-ligands. The reactivity of complexes in the ROP of ε-caprolactone (ε-CL) was studied. The highest activity was shown by complexes 5 and 8, containing phenyl groups at the terminal nitrogen atoms of the ligand in the ROP of ε-CL. Also, complex 5 was an effective initiator of copolymerization of 2-(benzyloxycarbonyl)-2-methyltrimethylene carbonate (TMCR) and L-lactide (L-LA) which led to the formation of a random copolymer.
设计开环聚合(ROP)无规共聚催化剂是一项实际任务。在本研究中,我们报告了基于二氨基原配体的铝络合物(R′=Et,R′′=Ph (5);R′=Bn,R′′=Ph (6);R′=t-Bu,R′′=Ph (7);R′=R′′=Ph (8))的合成。研究了配合物在ε-己内酯(ε-CL)的 ROP 中的反应活性。在 ε-CL 的 ROP 中,配体末端氮原子上含有苯基的配合物 5 和 8 的活性最高。此外,配合物 5 还是 2-(苄氧羰基)-2-甲基三亚甲基碳酸酯(TMCR)和 L-内酯(L-LA)共聚的有效引发剂,可形成无规共聚物。
{"title":"Diamidoamine Aluminum Complex as Effective Initiator for Random Copolymerization of Substituted Carbonate with L-Lactide","authors":"Milana U. Agaeva, Vladislav I. Filippenko, Badma N. Mankaev, Valeriia A. Serova, Konstantin A. Lyssenko, Elena V. Chernikova, Mikhail P. Egorov, Sergey S. Karlov","doi":"10.1021/acs.organomet.4c00078","DOIUrl":"https://doi.org/10.1021/acs.organomet.4c00078","url":null,"abstract":"Designing a catalyst for random copolymerization by ring-opening polymerization (ROP) is an actual task. In the present work, we report the synthesis of aluminum complexes (R′ = Et, R′′ = Ph (<b>5</b>); R′ = Bn, R′′ = Ph (<b>6</b>); R′ = <i>t</i>-Bu, R′′ = Ph (<b>7</b>); R′ = R′′ = Ph (<b>8</b>)] based on diamidoamine pro-ligands. The reactivity of complexes in the ROP of ε-caprolactone (ε-CL) was studied. The highest activity was shown by complexes <b>5</b> and <b>8</b>, containing phenyl groups at the terminal nitrogen atoms of the ligand in the ROP of ε-CL. Also, complex <b>5</b> was an effective initiator of copolymerization of 2-(benzyloxycarbonyl)-2-methyltrimethylene carbonate (TMC<sub>R</sub>) and <i>L</i>-lactide (<i>L</i>-LA) which led to the formation of a random copolymer.","PeriodicalId":56,"journal":{"name":"Organometallics","volume":null,"pages":null},"PeriodicalIF":2.8,"publicationDate":"2024-07-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141570234","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
Intrinsic Reactivity of [η5-1,3-(Me3C)2C5H3]2Th(bipy) toward Small Molecules η5-1,3-(Me3C)2C5H3]2Th(bipy)对小分子的内在反应性
IF 2.8 3区 化学 Q2 CHEMISTRY, INORGANIC & NUCLEAR Pub Date : 2024-07-05 DOI: 10.1021/acs.organomet.4c00149
Dongwei Wang, Yi Heng, Tongyu Li, Guofu Zi, Marc D. Walter
The reactivity of the thorium bipyridyl metallocene (Cp2tBu)2Th(bipy) (1; Cp2tBu = η5-1,3-(Me3C)2C5H3) toward a series of small molecules was explored, and the emerging reactivity pattern can be categorized: (1) It may act as a synthon for (Cp2tBu)2Th(II) in contact with alkynes, diazabutadienes, ketazine (Ph2C═N)2, o-benzoquinone, carbodiimides, organic azides, isothiocyanates, elemental sulfur (S8) and selenium (Se), and Ph2S2. (2) It participates in C–C coupling reactions with ketones Ph2CO, (CH2)5CO, and 1-indanone, aldehydes p-MePhCHO and p-ClPhCHO, amidate PhCONH(p-tolyl), seleno-ketone (p-MeOPh)2CSe, imines PhCH═NPh and (p-tolyl)2C═NH, ketazine (PhCH═N)2, and nitriles PhCN, Me3CCN, C6H11CN and CH3CN, to form (Cp2tBu)2Th[(bipy)(Ph2CO)] (15), (Cp2tBu)2Th[(bipy)((CH2)5CO)] (16), (Cp2tBu)2Th[(bipy)(1-(C8H8)CO)] (17), (Cp2tBu)2Th[(bipy)(p-MePhCHO)] (18), (Cp2tBu)2Th[(bipy)(p-ClPhCHO)] (19), (Cp2tBu)2Th[(bipy){PhCONH(p-tolyl)}] (20), (Cp2tBu)2Th[(bipy){(p-MeOPh)2CSe}] (21), (Cp2tBu)2Th[(bipy)(PhCHNPh)] (22), (Cp2tBu)2Th[(bipy){(p-tolyl)2CNH}] (23), (Cp2tBu)2Th[(bipy)(PhCHNN═CHPh)] (24), (Cp2tBu)2Th[(bipy)(PhCN)] (25), (Cp2tBu)2Th[(bipy)(Me3CCN)] (26), (Cp2tBu)2Th[(bipy)(C6H11CN)] (27), and (Cp2tBu)2Th[(bipy)(CH3CN)] (28), respectively. However, in the presence of benzyl nitrile PhCH2CN, the dimeric bis-amido complex {(Cp2tBu)2Th[NHC(CH2Ph)C(Ph)C(C(Ph)CN)NH]}2 (29) is isolated. (3) Isonitriles such as Me3CNC, Me3SiNC, and C6H11NC undergo C–N bond cleavage and C–C coupling to furnish the thorium isocyanido amido complexes (Cp2tBu)2Th[4-(Me3C)bipy](NC) (30), (Cp2tBu)2Th[4-(Me3Si)bipy](NC) (31), and (Cp2tBu)2Th[4-(C6H11)bipy](NC) (32), respectively. A comparison with related thorium bipyridyl meta
研究人员探索了钍双吡啶金属茂金属 (Cp2tBu)2Th(bipy) (1; Cp2tBu = η5-1,3-(Me3C)2C5H3)对一系列小分子的反应性,并将新出现的反应性模式进行了归类:(1) 在与炔烃、重氮丁二烯、氯哒嗪 (Ph2C═N)2、邻苯醌、碳化二亚胺、有机叠氮化物、异硫氰酸盐、元素硫 (S8) 和硒(Se)以及 Ph2S2 接触时,它可作为 (Cp2tBu)2Th(II) 的合成物。(2) 它参与与酮 Ph2CO、(CH2)5CO 和 1-茚酮,醛 p-MePhCHO 和 p-ClPhCHO,酰胺 PhCONH(对甲苯基),硒酮 (p-MeOPh)2CSe 的 C-C 偶联反应、亚胺 PhCH═NPh 和 (对甲苯基)2C═NH、甲嗪 (PhCH═N)2 以及腈 PhCN、Me3CCN、C6H11CN 和 CH3CN、形成 (Cp2tBu)2Th[(bipy)(Ph2CO)] (15)、(Cp2tBu)2Th[(bipy)((CH2)5CO)] (16)、(Cp2tBu)2Th[(bipy)(1-(C8H8)CO)] (17)、(Cp2tBu)2Th[(bipy)(p-MePhCHO)] (18), (Cp2tBu)2Th[(bipy)(p-ClPhCHO)] (19), (Cp2tBu)2Th[(bipy){PhCONH(p-tolyl)}] (20)、(Cp2tBu)2Th[(bipy){(p-MeOPh)2CSe}] (21), (Cp2tBu)2Th[(bipy)(PhCHNPh)] (22), (Cp2tBu)2Th[(bipy){(p-tolyl)2CNH}] (23)、(Cp2tBu)2Th[(bipy)(PhCHNN═CHPh)] (24)、(Cp2tBu)2Th[(bipy)(PhCN)] (25)、(Cp2tBu)2Th[(bipy)(Me3CCN)] (26)、(Cp2tBu)2Th[(bipy)(C6H11CN)] (27) 和 (Cp2tBu)2Th[(bipy)(CH3CN)] (28)。然而,在苄基腈 PhCH2CN 的存在下,分离出了二聚双氨基配合物 {(Cp2tBu)2Th[NHC(CH2Ph)C(Ph)C(C(Ph)CN)NH]}2 (29)。(3) Me3CNC、Me3SiNC 和 C6H11NC 等异腈通过 C-N 键裂解和 C-C 偶联生成钍异氰基氨基配合物 (Cp2tBu)2Th[4-(Me3C)bipy](NC)(30)、(Cp2tBu)2Th[4-(Me3Si)bipy](NC) (31) 和 (Cp2tBu)2Th[4-(C6H11)bipy](NC) (32)。与相关的钍联吡啶茂金属衍生物的比较表明,支持环戊二烯配体的微小变化调节了这些化合物的反应活性。
{"title":"Intrinsic Reactivity of [η5-1,3-(Me3C)2C5H3]2Th(bipy) toward Small Molecules","authors":"Dongwei Wang, Yi Heng, Tongyu Li, Guofu Zi, Marc D. Walter","doi":"10.1021/acs.organomet.4c00149","DOIUrl":"https://doi.org/10.1021/acs.organomet.4c00149","url":null,"abstract":"The reactivity of the thorium bipyridyl metallocene (Cp<sup>2<i>t</i>Bu</sup>)<sub>2</sub>Th(bipy) (<b>1</b>; Cp<sup>2<i>t</i>Bu</sup> = <i>η</i><sup>5</sup>-1,3-(Me<sub>3</sub>C)<sub>2</sub>C<sub>5</sub>H<sub>3</sub>) toward a series of small molecules was explored, and the emerging reactivity pattern can be categorized: (1) It may act as a synthon for (Cp<sup>2<i>t</i>Bu</sup>)<sub>2</sub>Th(II) in contact with alkynes, diazabutadienes, ketazine (Ph<sub>2</sub>C═N)<sub>2</sub>, <i>o</i>-benzoquinone, carbodiimides, organic azides, isothiocyanates, elemental sulfur (S<sub>8</sub>) and selenium (Se), and Ph<sub>2</sub>S<sub>2</sub>. (2) It participates in C–C coupling reactions with ketones Ph<sub>2</sub>CO, (CH<sub>2</sub>)<sub>5</sub>CO, and 1-indanone, aldehydes <i>p</i>-MePhCHO and <i>p</i>-ClPhCHO, amidate PhCONH(<i>p</i>-tolyl), seleno-ketone (<i>p</i>-MeOPh)<sub>2</sub>CSe, imines PhCH═NPh and (<i>p</i>-tolyl)<sub>2</sub>C═NH, ketazine (PhCH═N)<sub>2</sub>, and nitriles PhCN, Me<sub>3</sub>CCN, C<sub>6</sub>H<sub>11</sub>CN and CH<sub>3</sub>CN, to form (Cp<sup>2<i>t</i>Bu</sup>)<sub>2</sub>Th[(bipy)(Ph<sub>2</sub>CO)] (<b>15</b>), (Cp<sup>2<i>t</i>Bu</sup>)<sub>2</sub>Th[(bipy)((CH<sub>2</sub>)<sub>5</sub>CO)] (<b>16</b>), (Cp<sup>2<i>t</i>Bu</sup>)<sub>2</sub>Th[(bipy)(1-(C<sub>8</sub>H<sub>8</sub>)CO)] (<b>17</b>), (Cp<sup>2<i>t</i>Bu</sup>)<sub>2</sub>Th[(bipy)(<i>p</i>-MePhCHO)] (<b>18</b>), (Cp<sup>2<i>t</i>Bu</sup>)<sub>2</sub>Th[(bipy)(<i>p</i>-ClPhCHO)] (<b>19</b>), (Cp<sup>2<i>t</i>Bu</sup>)<sub>2</sub>Th[(bipy){PhCONH(<i>p</i>-tolyl)}] (<b>20</b>), (Cp<sup>2<i>t</i>Bu</sup>)<sub>2</sub>Th[(bipy){(<i>p</i>-MeOPh)<sub>2</sub>CSe}] (<b>21</b>), (Cp<sup>2<i>t</i>Bu</sup>)<sub>2</sub>Th[(bipy)(PhCHNPh)] (<b>22</b>), (Cp<sup>2<i>t</i>Bu</sup>)<sub>2</sub>Th[(bipy){(<i>p</i>-tolyl)<sub>2</sub>CNH}] (<b>23</b>), (Cp<sup>2<i>t</i>Bu</sup>)<sub>2</sub>Th[(bipy)(PhCHNN═CHPh)] (<b>24</b>), (Cp<sup>2<i>t</i>Bu</sup>)<sub>2</sub>Th[(bipy)(PhCN)] (<b>25</b>), (Cp<sup>2<i>t</i>Bu</sup>)<sub>2</sub>Th[(bipy)(Me<sub>3</sub>CCN)] (<b>26</b>), (Cp<sup>2<i>t</i>Bu</sup>)<sub>2</sub>Th[(bipy)(C<sub>6</sub>H<sub>11</sub>CN)] (<b>27</b>), and (Cp<sup>2<i>t</i>Bu</sup>)<sub>2</sub>Th[(bipy)(CH<sub>3</sub>CN)] (<b>28</b>), respectively. However, in the presence of benzyl nitrile PhCH<sub>2</sub>CN, the dimeric bis-amido complex {(Cp<sup>2<i>t</i>Bu</sup>)<sub>2</sub>Th[NHC(CH<sub>2</sub>Ph)C(Ph)C(C(Ph)CN)NH]}<sub>2</sub> (<b>29</b>) is isolated. (3) Isonitriles such as Me<sub>3</sub>CNC, Me<sub>3</sub>SiNC, and C<sub>6</sub>H<sub>11</sub>NC undergo C–N bond cleavage and C–C coupling to furnish the thorium isocyanido amido complexes (Cp<sup>2<i>t</i>Bu</sup>)<sub>2</sub>Th[4-(Me<sub>3</sub>C)bipy](NC) (<b>30</b>), (Cp<sup>2<i>t</i>Bu</sup>)<sub>2</sub>Th[4-(Me<sub>3</sub>Si)bipy](NC) (<b>31</b>), and (Cp<sup>2<i>t</i>Bu</sup>)<sub>2</sub>Th[4-(C<sub>6</sub>H<sub>11</sub>)bipy](NC) (<b>32</b>), respectively. A comparison with related thorium bipyridyl meta","PeriodicalId":56,"journal":{"name":"Organometallics","volume":null,"pages":null},"PeriodicalIF":2.8,"publicationDate":"2024-07-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141570235","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
In Silico Discovery of a Neutral 2π Aromatic Silicon Aluminum Compound 中性 2π 芳香族硅铝化合物的硅学发现
IF 2.8 3区 化学 Q2 CHEMISTRY, INORGANIC & NUCLEAR Pub Date : 2024-07-04 DOI: 10.1021/acs.organomet.4c00151
Himanshu Sharma, Kumar Vanka
The recently developed ab initio nanoreactor (AINR) approach to identifying reaction intermediates and pathways without the necessity of experimental input has been employed in the current work to locate new cyclic silicon-based structures that have the potential to display aromaticity. Using this approach, we have identified many cyclic silicon-based molecules that have been experimentally reported over the past three decades. More importantly, the current work showcases an interesting new molecule that has been discovered through this approach: a four-membered cyclic compound of silicon and aluminum that displays significant 2π aromaticity and is capable of the activation of important small molecules such as ammonia.
在目前的研究工作中,我们采用了最近开发的无须实验输入就能确定反应中间体和途径的非初始纳米反应器(AINR)方法,以找到有可能显示芳香性的新环状硅基结构。利用这种方法,我们发现了许多在过去三十年中被实验报告过的环硅分子。更重要的是,目前的研究工作展示了通过这种方法发现的一种有趣的新分子:一种由硅和铝组成的四元环状化合物,它具有显著的 2π 芳香性,能够活化氨等重要的小分子。
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引用次数: 0
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Organometallics
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