An organo-photocatalyzed visible-light-driven multi-component approach for carbothioaryl/alkylation of activated alkenes <i>via</i> C(sp<sup>3</sup>)–H bond functionalization

Das, Debabrata; Ghosh, Krishna Gopal; Garai, Sumit; Palasetty, Chandu; Devarajulu, Sureshkumar

doi:10.1039/d3ob01150j

Org. Biomol. Chem.

2023

DOI: 10.1039/d3ob01150j

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An organo-photocatalyzed visible-light-driven multi-component approach for carbothioaryl/alkylation of activated alkenes via C(sp³)–H bond functionalization

Debabrata Das,

Krishna Gopal Ghosh,

Sumit Garai

et al.

Abstract: A sustainable organo-photocatalyzed approach for carbothioaryl/alkylation of activated alkenes has been revealed via multi-component C(sp3)–H bond functionalization under a redox-neutral environment.

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2024

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Cited by 4 publications

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

Yang,

Liu,

Xie

2024

Advanced Science

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

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

Yang,

Liu,

Xie

2024

Advanced Science

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Pioneering Metal‐Free Late‐Stage C−H Functionalization Using Acridinium Salt Photocatalysis

Kanti Bera,

Porcheddu

2024

Chemistry A European J

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Using organic dyes as photocatalysts is an innovative approach to photocatalytic organic transformations. These dyes offer advantages such as widespread availability, adaptable absorption properties, and diverse chemical structures. Recent progress has led to the development of organic photocatalysts that can utilize visible light to modify chemically inert C‐H bonds. These catalysts are sustainable, selective, and versatile, enabling mild reactions, late‐stage functionalization, and various transformations in line with green chemistry principles. As catalysts in photoredox chemistry, they contribute to the development of efficient and environmentally friendly synthetic pathways. Acridinium‐based organic photocatalysts have proved valuable in late‐stage C‐H functionalization, enabling transformative reactions under mild conditions. This review emphasizes their innovative features, such as organic frameworks, efficient light absorption properties, and their applications in modifying complex molecules. It provides an overview of recent advancements in the use of acridinium‐based organic photocatalysts for late‐stage C‐H bond functionalization without the need for transition metals, showcasing their potential to expedite the development of new molecules and igniting excitement about the prospects of this research in the field.

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Harmonizing Visible‐Light in Green Synthesis: Unrevealing the Brilliance of Metal‐Free Cross‐Coupling of Unsaturated Hydrocarbons for C−C Bonds Formation

Patel,

Kumar Singh

2024

ChemPhotoChem

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Visible‐light induced, photoredox catalysis has opened a wide range in the transformation of organic compounds in recent times. In synthetic organic chemistry HAT (hydrogen atom transfer) and SET (single electron transfer) mechanisms are a very noteworthy routes that has opened a window in favor of C−C single bond formations. Usually, a major role of unsaturated hydrocarbons is to participate in carbon‐carbon bond formation as they carry reactive π‐bond. Under visible‐light, metal‐free cross‐coupling reactions are particularly favorable because of their atom economy, increased efficiency, and environmentally friendly procedures that result in the construction of C−C bonds. The review emphasizes the latest advancements of visible‐light mediated, cross‐coupling reactions of unsaturated hydrocarbons in metal‐free conditions for constructing carbon‐carbon single bonds.

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An organo-photocatalyzed visible-light-driven multi-component approach for carbothioaryl/alkylation of activated alkenes via C(sp³)–H bond functionalization

Abstract: A sustainable organo-photocatalyzed approach for carbothioaryl/alkylation of activated alkenes has been revealed via multi-component C(sp3)–H bond functionalization under a redox-neutral environment.

Cited by 4 publications

References 34 publications

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

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

Pioneering Metal‐Free Late‐Stage C−H Functionalization Using Acridinium Salt Photocatalysis

Harmonizing Visible‐Light in Green Synthesis: Unrevealing the Brilliance of Metal‐Free Cross‐Coupling of Unsaturated Hydrocarbons for C−C Bonds Formation

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An organo-photocatalyzed visible-light-driven multi-component approach for carbothioaryl/alkylation of activated alkenes via C(sp3)–H bond functionalization

Abstract: A sustainable organo-photocatalyzed approach for carbothioaryl/alkylation of activated alkenes has been revealed via multi-component C(sp3)–H bond functionalization under a redox-neutral environment.

Cited by 4 publications

References 34 publications

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

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

Pioneering Metal‐Free Late‐Stage C−H Functionalization Using Acridinium Salt Photocatalysis

Harmonizing Visible‐Light in Green Synthesis: Unrevealing the Brilliance of Metal‐Free Cross‐Coupling of Unsaturated Hydrocarbons for C−C Bonds Formation

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An organo-photocatalyzed visible-light-driven multi-component approach for carbothioaryl/alkylation of activated alkenes via C(sp³)–H bond functionalization