Metal-free oxysulfonylation and aminosulfonylation of alkenyl oximes: synthesis of sulfonylated isoxazolines and cyclic nitrones

Xu, Zhongqi; Zheng, Lin-Chuang; Lin, Li; Duan, Lili; Li, Yue‐Ming

doi:10.1039/c8ob02879f

Cited by 23 publications

(9 citation statements)

References 50 publications

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“…In 2019, the Li group used alkenyl oximes as starting materials in the C−S coupling with sulfonyl hydrazides (Eq. 38‐1) Intramolecular cyclization of alkenyl oximes generated two kinds of C‐centered radical intermediates.…”

Section: Sulfonyl Radiacls‐mediated Reactionsmentioning

confidence: 99%

Sulfonyl Hydrazides in Organic Synthesis: A Review of Recent Studies

et al. 2020

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Sulfonyl hydrazides are widely used as organic reagents. Advances in the past decade are summarized in the following categories by key intermediates: (1) [RO2S.]; (2) RO2SSR; (3) [ArS.]; (4) [RO2S−]; (5) RSO2‐[Metal] species; (6) Ar‐[Metal] species; (7) RSX; (8) RS‐DBU; (9) nucleophilic amino group; (10) sulfonyl hydrazides as diazene or sulfinic acid surrogate. Reactions with alkenes, alkynes, aldehydes, alcohols, thiophenol, Grignard reagents, among others, are discussed. We hope this review will promote future research in this area.

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Section: Sulfonyl Radiacls‐mediated Reactionsmentioning

confidence: 99%

Sulfonyl Hydrazides in Organic Synthesis: A Review of Recent Studies

et al. 2020

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“…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.…”

Section: Sulfonylation Reaction Using Sodium Sulfinatesmentioning

confidence: 91%

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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“…Another approach to the synthesis of isoxazolines with a sulfonyl moiety is the reaction of unsaturated oximes 155 with sulfonyl hydrazides 156 under the action of TBHP and a catalytic amount of iodine (Scheme 53) [142].…”

Section: Both Aliphatic (Example 118c) and Aromatic (Examplesmentioning

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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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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Metal-free oxysulfonylation and aminosulfonylation of alkenyl oximes: synthesis of sulfonylated isoxazolines and cyclic nitrones

Abstract: Sulfonylated isoxazolines and cyclic nitrones were obtained in moderate to excellent yields via iodine-catalyzed oxysulfonylation and aminosulfonylation of alkenyl oximes.

Cited by 23 publications

References 50 publications

Sulfonyl Hydrazides in Organic Synthesis: A Review of Recent Studies

Sulfonyl Hydrazides in Organic Synthesis: A Review of Recent Studies

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

Oxime radicals: generation, properties and application in organic synthesis

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