Planar-chiral arene ruthenium complexes: synthesis, separation of enantiomers, and application for catalytic C–H activation

Chemical Communications, Год журнала: 2024, Номер 60(33), С. 4491 - 4494

Опубликована: Янв. 1, 2024

The enantiomers of an arene ruthenium complex were separated by chromatography using auxiliary chiral phosphine. resolved planar-chiral catalyzed asymmetric C–H activation N -methoxy-benzamides.

Язык: Английский

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H₈‐BINOL‐Derived Chiral η⁶‐Benzene Ligands: New Opportunities for the Ruthenium‐Catalyzed Asymmetric C−H Activation

Angewandte Chemie International Edition, Год журнала: 2024, Номер 63(31)

Опубликована: Апрель 29, 2024

Abstract Given the tremendous success of (p‐cymene)Ru II ‐catalyzed C−H activation over past 20 years, community has long been aware that development chiral η 6 ‐benzene (Ben) ligands should be a potent strategy for achieving attractive but incredibly underdeveloped ruthenium(II)‐catalyzed asymmetric activation. However, it rarely achieved due to severe difficulty in developing proper Ben ligands. In particular, designing by connecting benzene fragment framework including rings remained an unsolved challenge until this effort. Here we present novel class axially derived from readily available ( S )‐5,5′,6,6′,7,7′,8,8′‐octahydro‐1,1′‐bi‐2‐naphthol (( )‐H 8 ‐BINOL) 4–8 steps. Notably, when coordinated with ruthenium, such ligand containing three only forms one possible isomeric BenRu complexes. The related catalysts could effectively catalyze N‐sulfonyl ketimines alkynes, affording range spirocyclic sultams up 99 % yield >99 ee. These are expected find broad applications future.

Язык: Английский

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Planar chiral arene ruthenium complexes derived from R-carvone

Dalton Transactions, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

Natural R -carvone was converted into ruthenium complexes with planar-chiral arene ligands. Similar to the classical [(cymene)RuCl 2 ] complex, they catalyse C–H activation reactions, albeit low stereoselectivity.

Язык: Английский

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Structurally diverse polyketides and alkaloids produced by a plant-derived fungus Penicillium canescens L1

Natural Products and Bioprospecting, Год журнала: 2025, Номер 15(1)

Опубликована: Апрель 3, 2025

A series of structurally diverse polyketides (1-3), sesterterpenoids (24 and 25), alkaloids (26-34) were isolated from the fermentation a plant-derived fungus Penicillium canescens L1 on solid rice medium. Among these secondary metabolites, penicanesols A-G (1-7) new structures, which elucidated by NMR, HR-ESI-MS, ECD calculation, X-ray diffraction. Penicanesol (1) represented rare dimer derived phthalan derivatives, characterized 5/6/6/6/5 heteropentacyclic core. The bioassay NCI-H1975 cell model showed that two compounds had good cytotoxic activities, most significant activate compound 13 an IC50 value 4.24 ± 0.13 μM, more than positive control drug (12.99 μM).

Язык: Английский

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Ruthenium catalyst with a planar-chiral arene ligand: synthesis, separation of enantiomers, and application in C-H activation of N-methoxy-benzamides

Опубликована: Янв. 11, 2024

Heating tert-butyl-tetraline with [(p-cymene)RuCl2]2 produces the racemic complex [(arene)RuCl2]2, which can be separated into enantiomers by chromatography of its diastereomeric adducts chiral phosphine ligand. The resolved catalyzes C-H activation N-methoxy-benzamides and their annulation N-vinyl-pivaloyl amide giving dihydroisoquinolones in 50-90% yields 70:30-90:10 enantiomeric ratio.

Язык: Английский

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The Difference in Ir-Catalyzed C(sp²)–H and C(sp³)–H Bond Activation Assisted by a Directing Group: Cyclometalation via Cis- or Trans-Chelation?

Inorganic Chemistry, Год журнала: 2024, Номер 63(38), С. 17626 - 17638

Опубликована: Сен. 5, 2024

Iridium-catalyzed C-H borylation of aromatic and aliphatic hydrocarbons assisted by a directing group was theoretically investigated. Density functional theory (DFT) calculations revealed both Ir-catalyzed C(sp

Язык: Английский

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A Chiral Amide Directing Group for Ruthenium-Catalyzed Asymmetric C–H Activation

Synfacts, Год журнала: 2024, Номер 20(03), С. 0318 - 0318

Опубликована: Фев. 14, 2024

Key words asymmetric C–H activation - chiral directing group ruthenium(II) catalysis

Язык: Английский

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H₈‐BINOL‐Derived Chiral η⁶‐Benzene Ligands: New Opportunities for the Ruthenium‐Catalyzed Asymmetric C−H Activation

Angewandte Chemie, Год журнала: 2024, Номер 136(31)

Опубликована: Апрель 29, 2024

Abstract Given the tremendous success of (p‐cymene)Ru II ‐catalyzed C−H activation over past 20 years, community has long been aware that development chiral η 6 ‐benzene (Ben) ligands should be a potent strategy for achieving attractive but incredibly underdeveloped ruthenium(II)‐catalyzed asymmetric activation. However, it rarely achieved due to severe difficulty in developing proper Ben ligands. In particular, designing by connecting benzene fragment framework including rings remained an unsolved challenge until this effort. Here we present novel class axially derived from readily available ( S )‐5,5′,6,6′,7,7′,8,8′‐octahydro‐1,1′‐bi‐2‐naphthol (( )‐H 8 ‐BINOL) 4–8 steps. Notably, when coordinated with ruthenium, such ligand containing three only forms one possible isomeric BenRu complexes. The related catalysts could effectively catalyze N‐sulfonyl ketimines alkynes, affording range spirocyclic sultams up 99 % yield >99 ee. These are expected find broad applications future.

Язык: Английский

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Sulfoximine Aided Ru(II)-Catalyzed Asymmetric Double C(sp²)–H Hydroarylations of Olefins

Organic Letters, Год журнала: 2024, Номер unknown

Опубликована: Окт. 21, 2024

Presented here is a sulfoximine-directed Ru(II)-catalyzed asymmetric intramolecular double C(sp

Язык: Английский

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Allylation of Lactol in Water

Organic Letters, Год журнала: 2024, Номер unknown

Опубликована: Ноя. 20, 2024

We developed a water-promoted cross-coupling of 3-hydroxyisobenzofuran-1(3

Язык: Английский

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