Direct C(sp3)-H functionalization with aryl and alkyl radicals as intermolecular hydrogen atom transfer (HAT) agents

Chemical Communications, Год журнала: 2024, Номер unknown

Опубликована: Янв. 1, 2024

Recent years have witnessed the emergence of direct intermolecular C(sp

Язык: Английский

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Photocatalytic α-C(sp³)–H Arylation/Heteroarylation of Amines Enabled by Pyrylium Salt

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Март 6, 2025

A general photocatalytic α-C(sp3)-H arylation/heteroarylation of amines has been developed. In the presence newly designed DPA-TPT, reaction can operate under mild conditions and produce a diverse array tertiary benzylic in good yields. Additionally, late-stage arylation tetracaine demonstrated practical application this protocol, highlighting its versatility efficiency functionalizing complex molecules.

Язык: Английский

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Dechlorinative Pyrazinylation of Glycine Derivatives

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Май 29, 2025

Amino acids and pyrazines both play crucial roles in drug design. Here, we present a visible-light-driven, redox-neutral α-C(sp3)-H pyrazinylation of glycine derivatives with chloropyrazines, enabling the efficient synthesis α-pyrazinyl valuable biological pharmaceutical potential.

Язык: Английский

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Copper-Photoredox-Catalyzed Divergent Strategy for the Site-Selective Arylation and Alkylation of Glycines and Peptides

ACS Catalysis, Год журнала: 2024, Номер 14(24), С. 18896 - 18906

Опубликована: Дек. 12, 2024

There is a scarcity of general strategies for the site-selective α–Csp3–H arylation glycine derivatives to synthesize nonproteinogenic α-arylglycines that occur frequently in commercial drugs and bioactive molecules. We disclose copper-photoredox-catalyzed using diaryliodonium reagents (DAIRs) as arylating agents. This strategy harnesses underexplored ability DAIRs serve agents under visible-light irradiation copper salts photocatalysts. The method applies glycine-selective C–H peptides with electronically structurally diverse DAIRs. Moreover, we demonstrate photoinduced copper-catalyzed single electron transfer (SET) can be coupled halogen atom (XAT) process presence alkyl iodides accomplish alkylation glycines peptides. In this synergistic SET/XAT approach, phenyl radicals generated from diphenyl iodonium triflate mediate XAT generate iodides. Both these methods operate mild conditions exhibit broad scope appreciable functional group tolerance. Overall, divergent toolbox presented here facilitate access various alkylated arylated enable bioconjugation between drug

Язык: Английский

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Photocatalytic Consecutive Photoinduced Electron Transfer-Enabled C(sp³)–H Pyridylation of Dihydroquinoxalin-2-ones

The Journal of Organic Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Ноя. 22, 2024

A photocatalytic decyanative C(sp3)–H pyridination of dihydroquinoxalin-2-ones with 4-cyanopyridines was developed by utilizing 4CzIPN as the photocatalyst. Mechanism studies show that this organophotocatalytic direct undergoes a radical–radical cross-coupling pathway promoted consecutive photoinduced electron transfer.

Язык: Английский

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Organophotocatalytic pyridination of N-arylglycines with 4-cyanopyridines by decarboxylative and decyanative radical-radical coupling

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(38), С. 7806 - 7810

Опубликована: Янв. 1, 2024

A photocatalytic decarboxylative aminoalkylation of 4-cyanopyridines with

Язык: Английский

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Photoredox-Catalyzed C–H Decyanative Pyridination of N-Arylated Glycine Derivatives with Cyanopyridines

Synfacts, Год журнала: 2024, Номер 20(07), С. 0768 - 0768

Опубликована: Июнь 14, 2024

Key words photocatalysis - pyridination N-aryl glycines cyanopyridines

Язык: Английский

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