Visible-Light-Catalyzed in Situ Denitrogenative Sulfonylation of Sulfonylhydrazones

Huang, Xiang; Chen, Xing; Xie, Haisheng; Tan, Zheng; Jiang, Huanfeng; Zeng, Wei

doi:10.1021/acs.orglett.1c02369

Cited by 14 publications

(6 citation statements)

References 60 publications

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“…in Scheme 4. The influence of the electron density of the Naryl moiety on the protocol's outcome was tested (37)(38)(39)(40)(41), revealing that electron-rich phenyl rings led to slightly low yields (38 and 41). The heteroaryl functionality of glycinate was successfully introduced using this procedure (42).…”

Section: Resultsmentioning

confidence: 99%

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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Section: Resultsmentioning

confidence: 99%

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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“…In 2021, Xie, Zeng, and co-workers introduced a photocatalytic method for synthesizing aryl or alkyl sulfones 106.2 (Scheme 106). 237 It was found that aryl or heteroaryl-substituted sulfonylhydrazones 106.1 worked well in this transformation. Similarly, sulfonylhydrazones derived from acetophenone, benzophenone, and benzocycloketone were also proven to be capable substrates (106.3−106.8).…”

Section: N-tosylhydrazonesmentioning

confidence: 98%

Visible Light-Induced Reactions of Diazo Compounds and Their Precursors

Zhang,

Gevorgyan

2024

Chem. Rev.

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In recent years, visible light-induced reactions of diazo compounds have attracted increasing attention in organic synthesis, leading to improvement of existing reactions, as well as to the discovery of unprecedented transformations. Thus, photochemical or photocatalytic generation of both carbenes and radicals provide milder tools toward these key intermediates for many valuable transformations. However, the vast majority of the transformations represent new reactivity modes of diazo compounds, which are achieved by the photochemical decomposition of diazo compounds and photoredox catalysis. In particular, the use of a redox-active photocatalysts opens the avenue to a plethora of radical reactions. The application of these methods to diazo compounds led to discovery of transformations inaccessible by the classical reactivity associated with carbenes and metal carbenes. In most cases, diazo compounds act as radical sources but can also serve as radical acceptors. Importantly, the described processes operate under mild, practical conditions. This Review describes this subfield of diazo compound chemistry, particularly focusing on recent advancements.

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“…In this regard, substantial progress in metal carbenoid intermediates has been demonstrated by the groups of Yu, 41 Valdés, 42 and Zhao 43 using catalysts based on transition metals, such as copper and iron, to access aryl alkyl sulfones via denitrogenation of tosylhydrazones (Scheme 1b, top). More recently, a photocatalytic strategy using an Ir catalyst 44 has been developed to achieve denitrogenative sulfonylation of tosylhydrazones to furnish aryl alkyl sulfones (Scheme 1b, bottom). The proposed intermediate of the reaction, a carbene radical cation generated from carbene by a photooxidant, is an elusive intermediate due to the higher electrophilicity of the carbene intermediate.…”

Section: Introductionmentioning

confidence: 99%

Denitrogenation of tosylhydrazones: synthesis of aryl alkyl sulfones catalyzed by a phenalenyl-based molecule

Kumar,

Datta,

Bhunia

et al. 2024

Catal. Sci. Technol.

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Visible-Light-Catalyzed in Situ Denitrogenative Sulfonylation of Sulfonylhydrazones

Abstract: A photocatalyzed in situ denitrogenative sulfonylation of N-arylsulfonyl hydrazones has been developed. This transformation provides a low-carbon strategy to assemble arylalkyl sulfones in a stepwise denitrogenation/sulfonylation manner.

Cited by 14 publications

References 60 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

Visible Light-Induced Reactions of Diazo Compounds and Their Precursors

Denitrogenation of tosylhydrazones: synthesis of aryl alkyl sulfones catalyzed by a phenalenyl-based molecule

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