Aluminum-Containing Heterobimetallic Complexes as Versatile Platforms for Homogeneous Catalysis

ACS Catalysis, Год журнала: 2023, Номер 13(19), С. 12519 - 12542

Опубликована: Сен. 11, 2023

Within the broader area of heterobimetallic catalysis, Al/M compounds (M = any metal) are promising for design and execution catalytic manifolds. This Perspective reviews recent advances in focusing on their applications. Topics include polymerization, epoxide activation carbonylation, C–H functionalization, other important transformations mediated by catalysts. In each case, mechanistic role aluminum site is highlighted. A broad range Al-containing metalloligands combinations included to construct this comprehensive perspective.

Язык: Английский

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Ligand-ligated Ni–Al bimetallic catalysis for C–H and C–C bond activation

Chemical Communications, Год журнала: 2022, Номер 58(88), С. 12260 - 12273

Опубликована: Янв. 1, 2022

Compared with non-ligated Ni-Al bimetallic catalysis, bifunctional ligand-ligated catalysis displays stronger synergism, not only affecting the electronic properties and steric hindrance of substrates, but also producing a directing effect for facile control reactivity, site selectivity enantioselectivity in activation C-H C-C bonds. This review will give brief summary research advances this field, highlighting development ligands their applications.

Язык: Английский

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Enantioselective Nickel‐Catalyzed C(sp³)−H Activation of Formamides

Angewandte Chemie International Edition, Год журнала: 2022, Номер 61(42)

Опубликована: Авг. 29, 2022

Enantioselective Ni-catalyzed C(sp3 )-H bond activation remains an elusive challenge. Herein, we used phosphine oxide-ligated Ni-Al bimetallic catalyst to realize enantioselective aliphatic of formamides, providing a series chiral N-containing heterocycles in 40-95 % yield and 70-95 ee.

Язык: Английский

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Enantioselective Synthesis of Axially Chiral 1-Arylisoquinolines by Iridium(I)-Catalyzed Hydroarylation of Alkynes

Synlett, Год журнала: 2023, Номер 34(12), С. 1442 - 1446

Опубликована: Янв. 29, 2023

Abstract Ir(I)-catalyzed atroposelective hydroarylation of alkynes with 1-arylisoquinolines through C–H functionalization was realized. In the presence 5 mol% [Ir(cod)Cl]2 and 10 QUINOX-P, a wide range axially chiral alkenylated biaryls were obtained in up to 98% yield 97% ee. Notably, only one equivalent alkyne required guarantee high efficiency this process. This reaction exhibits excellent functional-group tolerance under mild conditions.

Язык: Английский

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Ni‐SPO‐Al Catalyzed Stereoselective C–H Alkenylation of Quinazolinones with Alkynes to Prepare trans‐Isomers

European Journal of Organic Chemistry, Год журнала: 2025, Номер 28(5)

Опубликована: Янв. 4, 2025

Abstract A stereoselective Ni−Al bimetal‐catalyzed C−H alkenylation of quinazolinones with alkynes has been successfully developed. Good selectivity Z‐type quinazolinone products was obtained using readily available substrates, which exhibits a trans‐configuration opposite to the conventional alkynylation reactions and improves diversity compounds. In addition, reaction process further explored through KIE other control experiments, possible mechanism proposed.

Язык: Английский

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Iron-Catalyzed Regio- and Stereoselective C–H Alkenylation of Pivalophenone Derivatives with Unsymmetric Internal Alkynes

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(3), С. 1890 - 1897

Опубликована: Янв. 13, 2023

Here we report an ortho-C-H alkenylation of aromatic ketones with unsymmetric internal alkynes catalyzed by iron phosphine complex, Fe(PMe3)4. The use a catalytic amount PtBu3 as additive was found to improve the product yields. proceeds regio- and stereoselectively give corresponding styrene derivatives.

Язык: Английский

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C–H Functionalization of Arenes via NHC-Supported Ni/Al Bimetallic Catalysis

Synthesis, Год журнала: 2023, Номер 55(24), С. 4049 - 4061

Опубликована: Июнь 21, 2023

Abstract Despite the C–H functionalization of arenes offering an efficient synthetic route towards functionalized aromatic compounds with high atom- and step-economy, low reactivity bond makes this transformation rather challenging. Compared mono-metal catalysis, introduction bimetallic catalysis would greatly enhance selectivity transformation. In review, we highlight recent progress in via NHC-Ni/Al catalysis. The added aluminum as a co-catalyst activate arene through Lewis acid-base interaction, regioselectivity could be controlled synergism NHC-Ni Al. This strategy also applied enantioselective alkylation well-designed chiral NHC ligands. 1 Introduction 2 Addition to Alkynes Activation 3 Alkylation Ni/Al Bimetallic Catalysis 3.1 Racemic Hydroarylation Alkenes 3.2 Asymmetric 4 Conclusion Outlook

Язык: Английский

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Site‐Selective C−H Alkenylation of N‐Heteroarenes by Ligand‐Directed Co/Al and Co/Mg Cooperative Catalysis**

Angewandte Chemie International Edition, Год журнала: 2023, Номер 62(17)

Опубликована: Март 1, 2023

Abstract We report herein the design and development of Co/Al Co/Mg bimetallic catalysts, supported by a phosphine/secondary phosphine oxide (PSPO) bifunctional ligand, for site‐selective C−H alkenylation nitrogen‐containing heteroarenes with alkynes. These catalysts enable pyridine, pyridone, imidazo[1,2‐ ]pyridine derivatives at site proximal to Lewis basic nitrogen or oxygen atom, which represents selectivity profile distinct from that previously developed cobalt‐diphosphine/aluminum catalyst. The alkenylated products were obtained in moderate good yields using various heterocycles differently substituted internal Kinetic isotope effect experiments suggest irreversibility activation step, relevance rate‐limiting step depends on reaction conditions. Density functional theory calculations indicate ligand‐to‐ligand hydrogen transfer is common mechanism activation.

Язык: Английский

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Exploration of Compounds with 2-Phenylbenzo[d]oxazole Scaffold as Potential Skin-Lightening Agents through Inhibition of Melanin Biosynthesis and Tyrosinase Activity

Molecules, Год журнала: 2024, Номер 29(17), С. 4162 - 4162

Опубликована: Сен. 2, 2024

Inspired by the potent tyrosinase inhibitory activity of phenolic compounds with a 2-phenylbenzo[d]thiazole scaffold, we explored 1–15 2-phenylbenzo[d]oxazole, which is isosterically related to 2-phenylbenzo[d]thiazole, as novel inhibitors. Among these, 3, 8, and 13, featuring resorcinol structure, exhibited significantly stronger mushroom inhibition than kojic acid, compound 3 showing nanomolar IC50 value 0.51 μM. These results suggest that plays an important role in inhibition. Kinetic studies using Lineweaver–Burk plots demonstrated mechanisms while docking simulation indicated structure contributed binding through hydrophobic hydrogen bonding interactions. Additionally, these effectively inhibited melanin production B16F10 cells situ concentration-dependent manner. As showed no cytotoxicity epidermal cells, melanocytes, or keratinocytes, they are appropriate for skin applications. Compounds 8 13 substantially higher depigmentation effects on zebrafish larvae even at 800- 400-times lower concentrations respectively. findings 2-phenylbenzo[d]oxazole promising candidate

Язык: Английский

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Intermolecular Carbophosphination of Alkynes with Phosphole Oxides via Ni−Al Bimetal‐Catalyzed C−P Bond Activation

Angewandte Chemie International Edition, Год журнала: 2023, Номер 62(49)

Опубликована: Окт. 17, 2023

Intermolecular carbophosphination reaction of alkynes or alkenes with unreactive C-P bonds remains an elusive challenge. Herein, we used a Ni-Al bimetallic catalyst to realize intermolecular 5-membered phosphole oxides, providing series 7-membered phosphepines in up 94 % yield.

Язык: Английский

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