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

Chemical Communications, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

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

Language: Английский

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

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: March 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.

Language: Английский

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Dechlorinative Pyrazinylation of Glycine Derivatives

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: May 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.

Language: Английский

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

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(24), P. 18896 - 18906

Published: Dec. 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

Language: Английский

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

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 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.

Language: Английский

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

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(38), P. 7806 - 7810

Published: Jan. 1, 2024

A photocatalytic decarboxylative aminoalkylation of 4-cyanopyridines with

Language: Английский

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

Synfacts, Journal Year: 2024, Volume and Issue: 20(07), P. 0768 - 0768

Published: June 14, 2024

Key words photocatalysis - pyridination N-aryl glycines cyanopyridines

Language: Английский

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