Visible-Light Photoredox-Catalyzed Regioselective Sulfonylation of Alkenes Assisted by Oximes via [1,5]-H Migration

Yang, Shichao; Wang, Lei; Wang, Lulu; Li, Hongji

doi:10.1021/acs.joc.9b02646

Cited by 37 publications

(16 citation statements)

References 77 publications

(36 reference statements)

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“…The authors proposed a radical mechanism in which the addition of the sulfonyl radical to the double C=C bond, is followed by 1,5-HAT from the oxime hydroxy group to the carbon radical. An experiment with a deuterium label on the hydroxy group of oxime confirmed this hypothesis: the deuterium was found at the β-carbon atom of the product [155]. lated in 92% yield instead of 194a when TEMPO was added to the reaction mixture.…”

Section: Various Disulfides Of Both Aromaticmentioning

confidence: 86%

“…Under irradiation of blue LED (450-455 nm) of the mixture of oximes 189, sulfonyl hydrazides 190, silver(I) oxide and disodium salt of eosin Y in an inert atmosphere sulfones 191 are formed [155] (Scheme 66). In this case, hydrosulfonylation of the C=C double bond takes place instead of typical cyclization of β,γ-unsaturated oximes 189 to isoxazolines.…”

Section: Various Disulfides Of Both Aromaticmentioning

confidence: 99%

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Oxime radicals: generation, properties and application in organic synthesis

Krylov¹,

Paveliev²,

Budnikov³

et al. 2020

Beilstein J. Org. Chem.

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N-Oxyl radicals (compounds with an N–O• fragment) represent one of the richest families of stable and persistent organic radicals with applications ranging from catalysis of selective oxidation processes and mechanistic studies to production of polymers, energy storage, magnetic materials design and spectroscopic studies of biological objects. Compared to other N-oxyl radicals, oxime radicals (or iminoxyl radicals) have been underestimated for a long time as useful intermediates for organic synthesis, despite the fact that their precursors, oximes, are extremely widespread and easily available organic compounds. Furthermore, oxime radicals are structurally exceptional. In these radicals, the N–O• fragment is connected to an organic moiety by a double bond, whereas all other classes of N-oxyl radicals contain an R2N–O• fragment with two single C–N bonds. Although oxime radicals have been known since 1964, their broad synthetic potential was not recognized until the last decade, when numerous selective reactions of oxidative cyclization, functionalization, and coupling mediated by iminoxyl radicals were discovered. This review is focused on the synthetic methods based on iminoxyl radicals developed in the last ten years and also contains some selected data on previous works regarding generation, structure, stability, and spectral properties of these N-oxyl radicals. The reactions of oxime radicals are classified into intermolecular (oxidation by oxime radicals, oxidative C–O coupling) and intramolecular. The majority of works are devoted to intramolecular reactions of oxime radicals. These reactions are classified into cyclizations involving C–H bond cleavage and cyclizations involving a double C=C bond cleavage.

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Section: Various Disulfides Of Both Aromaticmentioning

confidence: 86%

Section: Various Disulfides Of Both Aromaticmentioning

confidence: 99%

Oxime radicals: generation, properties and application in organic synthesis

Krylov¹,

Paveliev²,

Budnikov³

et al. 2020

Beilstein J. Org. Chem.

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show abstract

“…The reaction of ketoximes with sulfonyl hydrazides was also realized by Li and Duan group [107] . Different from Li's work, [106] sulfonylated isoxazolines were obtained in moderate to excellent yields in this reaction. Using iodine as the catalyst and TBHP as the oxidant, various sulfonylated isoxazolines were obtained in moderate to excellent yields.…”

Section: Sulfonylation Reaction Using Sodium Sulfinatesmentioning

confidence: 92%

“…In 2020, a visible-light photoredox-catalyzed regioselective sulfonylation of alkenes with sulfonyl hydrazides assisted by oximes was delivered by Li group. [106] The hydroxyl group within oximes played an important role in this transformation. Sulfonyl radical was generated from the interaction of TsNHNH 2 with Ag 2 O.…”

Section: Sulfonylation/noncyclization With Alkenesmentioning

confidence: 99%

Recent Progress in Sulfonylation via Radical Reaction with Sodium Sulfinates, Sulfinic Acids, Sulfonyl Chlorides or Sulfonyl Hydrazides

et al. 2020

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Sodium sulfinates, sulfinic acids, sulfonyl chlorides and sulfonyl hydrazides as readily available and efficient sulfonylation reagents have been extensively explored in recent years. Sulfonyl radical can be generated from these sulfonyl reagents via different methods, then the sulfonyl radical could react with various substrates via different pathways to afford the corresponding products. In this review, we will summarize the progress in sulfonylation via radical reaction using sodium sulfinates, sulfinic acids, sulfonyl chlorides and sulfonyl hydrazides in recent three years. In terms of the different sulfonylation reagents, we classify these sulfonylation reactions into four types: 1.

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“…2 In the past few years, a significant renaissance of photocatalysis in the field of organic chemistry has been seen 7,[23][24][25][26][27][28][29][30][31][32][33] since the pioneer works reported by MacMillan 34 and Yoon 35 in 2008. With the assistance of visible light, RCF 2 X could serve as an important synthon for difluoroalkylation reactions in organic chemistry.…”

Section: Introductionmentioning

confidence: 99%