Stabilized Carbon‐Centered Radical‐Mediated Carbosulfenylation of Styrenes: Modular Synthesis of Sulfur‐Containing Glycine and Peptide Derivatives

Advanced Science, Год журнала: 2024, Номер 11(29)

Опубликована: Июнь 9, 2024

Abstract Sulfur‐containing amino acids and peptides play critical roles in organisms. Thiol‐ene reactions between the thiol residues of L ‐cysteine alkenyl fragments designed coupling partners serve as primary tools for constructing C─S bonds synthesis unnatural sulfur‐containing acid derivatives. These are favored due to preference hydrogen transfer from β‐sulfanyl carbon radical intermediates. In this paper, study proposes utilizing carbon‐centered radicals stabilized by capto‐dative effect, generated under photocatalytic conditions N –aryl glycine The aim is compete with hydrogen, enabling C─C bond formation radicals. This protocol robust presence air water, offers significant potential a modular efficient platform synthesizing modifying peptides, particularly abundant disulfides styrenes.

Язык: Английский

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Photoredox-catalyzed three-component alkylation of glycine derivatives and peptides via a site-selective 1,5-hydrogen atom transfer cascade

Organic Chemistry Frontiers, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

We report a visible-light-mediated three-component reaction via 1,5-HAT combined with site-selective remote C(sp 3 )–H cross-coupling reactions of alkenes alkyl radicals for the α-C(sp alkylation glycine derivatives and peptides.

Язык: Английский

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Trifluoromethylthiolation Carbonylation of Unactivated Alkenes via Distal Migration

Organic Letters, Год журнала: 2024, Номер unknown

Опубликована: Ноя. 20, 2024

Sulfur-containing compounds represent a significant category of organic compounds, and the introduction sulfur groups into can effectively enhance their biological activity synthetic diversity. Although variety difunctionalization reactions alkenes based on radicals have been documented, challenges remain in carbonylative unactivated by addition radical. Herein, we present trifluoromethylthiolative carbonylation reaction alkenes, which goes through trifluoromethylthiol radical to then newly generated carbon intermediate. A heterocyclic/aryl migration presence monoxide is crucial for success this methodology finally resulted formation sulfur-containing carbonylated products good yields.

Язык: Английский

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Stabilized Carbon Radical‐Mediated Assembly of Arylthianthrenium Salts, Alkenes and Amino Acid/Peptide Derivatives

Advanced Science, Год журнала: 2024, Номер 12(2)

Опубликована: Ноя. 21, 2024

Abstract Efficiently assembling amino acids and peptides with bioactive molecules facilitates the modular streamlined synthesis of a diverse library peptide‐related compounds. Particularly notable is their application in pharmaceutical development, leveraging site‐selective late‐stage functionalization. Here, visible light‐induced three‐component reaction involving arylthianthrenium salts, acid/peptide derivatives, alkenes are introduced. This approach utilizes captodatively‐stabilized carbon radicals to enable radical‐radical C─C coupling, effectively constructing complex molecules. method offers promising alternative route for peptide‐derived bio‐relevant compounds

Язык: Английский

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Photoinduced azidoalkylation of amino acid and peptide derivatives using sulfur hexafluoride as an electron scavenger

Cell Reports Physical Science, Год журнала: 2024, Номер 5(11), С. 102256 - 102256

Опубликована: Окт. 28, 2024

Язык: Английский

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