Blue light induced [2,3]-sigmatropic rearrangement reactions of tosylhydrazones

Wang, Yuerong; Jia, Ping; Hao, Yingdi; Li, Jianglian; Lai, Ruizhi; Guo, Li; Wu, Yong

doi:10.1016/j.tetlet.2022.154098

Cited by 6 publications

(3 citation statements)

References 74 publications

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“…In this scenario, N−H insertion products 105.6 were observed. Moreover, the employment of N-tosylhydrazones under photochemical conditions for X−H (X = C, N, O, S) insertions, 234 [2 + 1] cycloadditions, 235 Doyle−Kirmse and Sommelet−Hauser reactions, 236 was also reported.…”

Section: N-tosylhydrazonesmentioning

confidence: 99%

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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Section: N-tosylhydrazonesmentioning

confidence: 99%

Visible Light-Induced Reactions of Diazo Compounds and Their Precursors

Zhang,

Gevorgyan

2024

Chem. Rev.

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“…[11] Exploring more efficient method to synthesize these useful scaffolds is highly desirable. [2,3] sigmatropic rearrangement reaction, [12] such as Doyle-Kirmse rearrangement and Sommelet-Hauser rearrangement, or Stevens rearrangement [12b,13] are very effective strategies for the construction of complex compounds. Among them, Sommelet-Hauser rearrangement is an attractive reaction, which involves an aromatic unsaturated double bond and provides a unique method for the synthesis of sulfur/ selenium-containing vinylogous carbonates or ortho-substituted aromatic compounds with a tertiary carbon center.…”

Section: Introductionmentioning

confidence: 99%

Sulfoxonium Ylides as Carbene Precursors in Rhodium‐Catalyzed Sommelet‐Hauser Rearrangement for the Synthesis of S/Se‐Containing Compounds

Luo,

Lin,

Hao

et al. 2023

Eur J Org Chem

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Rhodium‐catalyzed Sommelet‐Hauser rearrangement derived from α‐thioesters/α‐selenoesters and sulfoxonium ylides has been developed for the synthesis of various sulfur/selenium‐containing ortho‐substituted aromatic compounds in medium to excellent yields (39 examples; up to 97 %). Sulfoxonium ylides as the safe carbene precursors are firstly used in Sommelet‐Hauser rearrangement reactions, which is superior to traditional diazo compounds. The present reaction has the advantages of mild condition, safety and broad substrate scope, which afford a unique method for the synthesis of sulfur/selenium‐containing compounds with a tertiary carbon center.

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“…3 When it comes to less colored acceptor-only diazo compounds, however, the direct photolysis becomes less attractive; instead triplet sensitization with an appropriate photosensitizer is more favorable. [4][5][6][7][8][9][10][11][12] Several research groups have recently reported on their studies and could show that such triplet sensitization leads to the formation of a triplet carbene intermediate, [5][6][7][8][9][10][11][12] which is witnessed, e.g. in stereoconvergent cyclopropanation reactions, 11 or gem-difluoroolefination reactions.…”

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confidence: 99%

Photocatalytic [2,3]-Sigmatropic Rearrangement Reactions of Ethyl Diazoacetate

M. Bopape,

Shah,

Koenigs

2023

Synlett

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Herein, we describe a photocatalytic reaction of diazo compounds with allyl sulfides under visible light reaction conditions. In the presence of Ru(bpy)3Cl2 as photocatalyst, a [2,3]-sigmatropic rearrangement reaction occurs, which leads to formation of homoallylic sulfides. This reaction proceeds in acetone as solvent, which is unusual in carbene transfer reactions, and shows a good substrate scope in the rearrangement reaction of allylic sulfides.

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Blue light induced [2,3]-sigmatropic rearrangement reactions of tosylhydrazones

Cited by 6 publications

References 74 publications

Visible Light-Induced Reactions of Diazo Compounds and Their Precursors

Visible Light-Induced Reactions of Diazo Compounds and Their Precursors

Sulfoxonium Ylides as Carbene Precursors in Rhodium‐Catalyzed Sommelet‐Hauser Rearrangement for the Synthesis of S/Se‐Containing Compounds

Photocatalytic [2,3]-Sigmatropic Rearrangement Reactions of Ethyl Diazoacetate

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