Tetrabutylammonium iodide catalyzed allylic sulfonylation of Baylis–Hillman acetates with sulfonylhydrazides in water

Li, Xiaoqing; Xu, Xiangsheng; Tang, Yucai

doi:10.1039/c3ob27329f

Cited by 99 publications

(34 citation statements)

References 31 publications

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“…The Li group established two kinds of reactions with terminal alkenes via the TBAI/TBHP‐promoted addition‐elimination. The H‐abstraction from in situ generated tert ‐butoxyl or/and tert ‐butylperoxy radicals provided an access to internal alkenes.…”

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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“…Later, the authors applied this system for the sulfonylation of Baylis-Hillman acetates delivering allyl sulfones in 43-78% yields. [16] Allyl alcohols and sulfinic acids were also used as starting reagents for the synthesis of allyl sulfones. [17] Another group of methods of the double bond oxidative sulfonylation is based on the application of iodide/transition metal salt system.…”

Section: Sulfonylation Of Alkenesmentioning

confidence: 99%

Oxidative Sulfonylation of Multiple Carbon‐Carbon bonds with Sulfonyl Hydrazides, Sulfinic Acids and their Salts

et al. 2020

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Oxidative coupling methodology is widely applied for the formation of carbon-carbon and carbon-heteroatom bonds. This review focuses on methods for oxidative sulfonylation of multiple bonds involving sulfonyl hydrazides, sulfinic acids and their salts as sulfonylation reagents. Under oxidative conditions, they generate sulfonyl radicals, trapped by multiple carbon-carbon bonds resulting in a variety of SO 2-containing products: mainly, vinyl and alkynyl sulfones, hydroxy-, keto, and halo-substituted sulfones, sulfonylated derivatives of carbo-and heterocycles. This exhaustive review summarizes 321 references from 1996 to 2020 with the specialization of the studies of the last five years, and is divided into the chapters according to the classes of compounds being sulfonylated.

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“…[20,21] Therefore, a clean and economical S-allylation is still a very attractive goal for the construction of carbon-sulfur bonds, especially in functionalized allylic compounds such as Baylis-Hillman (BH) adducts. As it so happens, reactions of acyclic BH acetates with thiols, [22,23] sulfonylhydrazides, [24] and thiolacetic acid, [25] under basic conditions, afforded the corresponding S N 2 products whereas treatment of acyclic BH alcohols [22,26] or their corresponding tert-butyldimethylsilyl ethers [22] with thiols resulted in the formation of Michael adducts.…”

Section: Introductionmentioning

confidence: 97%