Potassium iodide-mediated radical arylsulfonylation/1,2-carbon migration sequences for the synthesis of β-sulfonated cyclic ketones

Kim, Yeon Joo; Choo, Mi Hyeon; Kim, Dae Young

doi:10.1016/j.tetlet.2018.09.027

Cited by 22 publications

(9 citation statements)

References 92 publications

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“…This methodology was advanced by Paquette (1998) (b), who prepared brominated spirocyclic compounds 6 from dihydrofurans 5 . Dake (2004) (c) replaced the dihydrofuran moiety with tetrahydropyridines 7 to form the spirocycle 8 in 96% yield. − Furthermore, modifications to the previous work have recently been developed to include similar 1,2-carbon migration sequences with concomitant trifluoromethylation, arylation or arylsulfonylation under visible-light or transition-metal-free induction. − …”

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confidence: 63%

Regioselective Transition-Metal-Free Oxidative Cyclobutanol Ring Expansion to 4-Tetralones

et al. 2018

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A facile and transition-metal-free ring expansion of the cyclobutanol moiety to 4-tetralones fused to heteroaromatic systems is described. The oxidative ring expansion proceeds rapidly and regioselectively through mediation by N-bromosuccinimide and acetonitrile in satisfactory to good yields. The preparation of precursors and the ring expansion have proven to be scalable and are straightforward to carry out.

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confidence: 63%

Regioselective Transition-Metal-Free Oxidative Cyclobutanol Ring Expansion to 4-Tetralones

et al. 2018

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“…In 2019, The Kim group studied the effect of different alkenyl cyclobutanols in the synthesis of β ‐sulfonated cyclic ketones. The radical addition/ ring‐expansion cascade could be triggered by KI/18‐crown‐6/TBHP system in aqueous media (Eq.…”

Section: Sulfonyl Radiacls‐mediated Reactionsmentioning

confidence: 99%

“…The radical addition/ ring‐expansion cascade could be triggered by KI/18‐crown‐6/TBHP system in aqueous media (Eq. 19‐1) or electrochemical oxidative pathway (Eq. 19‐2) (Scheme ).…”

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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“…With the aid of oxidants 77,78 or under electrochemical conditions, 79,80 sulfonyl hydrazines or sulfinates can react with 1-…”

Section: Sulfonylation-rearrangementmentioning

confidence: 99%

Organic Sulfinic Acids and Salts in Visible Light-Induced Reactions

Shang

Lü

2021

Synthesis

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Sulfinic acids and their salts are a useful source of sulfur-containing structures. Photocatalysis of these compounds with visible light enables chemists to achieve various transformations under mild conditions. This review article summarizes visible light-induced reactions of sulfinic acids and their salts. This article is organized by reaction type and brief discussions on plausible reaction mechanisms for typical transformations are presented.

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Potassium iodide-mediated radical arylsulfonylation/1,2-carbon migration sequences for the synthesis of β-sulfonated cyclic ketones

Cited by 22 publications

References 92 publications

Regioselective Transition-Metal-Free Oxidative Cyclobutanol Ring Expansion to 4-Tetralones

Regioselective Transition-Metal-Free Oxidative Cyclobutanol Ring Expansion to 4-Tetralones

Sulfonyl Hydrazides in Organic Synthesis: A Review of Recent Studies

Organic Sulfinic Acids and Salts in Visible Light-Induced Reactions

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