Cobalt-Catalyzed Chemoselective π–σ–π-Type Tandem Reductive Coupling to Access Isoquinolines via Carbocobaltation of Nitriles

ACS Catalysis, Год журнала: 2025, Номер 15(3), С. 1596 - 1606

Опубликована: Янв. 14, 2025

Transition metal-catalyzed reductive coupling chemistry has been recognized as a powerful tool for the synthesis of diverse organic molecules. However, despite enormous progress in this field, there is no precedent tandem widely accessible nitriles with electrophiles that contain σ- and π-type (σ/π-type) electrophilic functional groups simultaneously. Herein, we have established unique cobalt catalysis system, enabling chemoselective coupling/tandem cyclization reaction aryl halides (Br, Cl, I) bearing carbonyl moiety variety aryl, alkenyl, alkyl via carbocobaltation unknown yet. The protocol allows modular structurally isoquinolines wide substrate scope (>60 examples), good functionalities tolerance, chemoselectivity.

Язык: Английский

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Nickel-Catalyzed Dynamic Kinetic Asymmetric Reductive Arylation of Aldehydes with Heterobiaryl Triflates

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Март 15, 2025

In this context, we report a nickel-catalyzed dynamic kinetic asymmetric reductive arylation of aldehydes with racemic heterobiaryl triflates, offering series axially chiral heterobiaryls bearing centrally secondary alcohol moiety in highly diastereo- and enantioselective manner. The simultaneous control both axial central stereogenic elements the products lies stereoselective nucleophilic addition configurationally labile hetereobiaryl nickel complex to formyl group aldehydes.

Язык: Английский

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Enantioselective Desymmetrization of Biaryls via Cooperative Photoredox/Brønsted Acid Catalysis and Its Application to the Total Synthesis of Ancistrobrevolines

Journal of the American Chemical Society, Год журнала: 2025, Номер unknown

Опубликована: Апрель 5, 2025

Photoredox catalysis has emerged as a powerful tool for forming and breaking chemical bonds, further taking hold with its integration asymmetric catalysis. While the dual-catalytic approach led to successful examples of control stereogenic centers, axes remained underexplored. In this study, an acylimine intermediate was generated through photoredox catalysis, symmetric substrate, 2-arylresorcinol, desymmetrized aid chiral phosphoric acid Using approach, center axis were successfully controlled provide natural-product-driven compound. The origins enantioselectivity diastereoselectivity investigated density functional theory study four possible enantiodetermining transition states. Consequently, first total syntheses ring-contracted naphthylisoquinoline alkaloid ancistrobrevolines A B accomplished concisely. This provides not only novel methodology strategy synthesize alkaloids but also direction advance catalytic research synthesis studies.

Язык: Английский

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Visible Light-Driven Construction of Axially Chiral Heterocyclic Compounds

Topics in heterocyclic chemistry, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

Язык: Английский

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Reduction of unactivated alkyl chlorides enabled by light-induced single electron transfer

Science China Chemistry, Год журнала: 2023, Номер 67(2), С. 471 - 481

Опубликована: Ноя. 16, 2023

Язык: Английский

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