Visible-light-initiated regioselective sulfonylation/cyclization of 1,6-enynes under photocatalyst- and additive-free conditions

Meng, Xiaoxiao; Kang, Qing‐Qing; Zhang, Jun‐Yao; Li, Qiang; Wei, Wanzhi; He, Wei‐Min

doi:10.1039/c9gc03769a

Cited by 119 publications

(35 citation statements)

References 64 publications

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“…Remarkably, alkyl sulfonyl hydrazide (R=Et) was also efficient radical source, providing the product in 56% yield. Recently, the Wei group has developed a series of cascade reactions about 1,6‐enynes with similar mechanism. The Guo group reported one example of radical triggered 6‐exo‐dig cyclization for the synthesis of 3,4‐dihydroquinolin‐2(1H)‐ones (Eq.…”

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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“…Without employing any photocatalyst and additive, the visible‐light‐initiated regioselective sulfonylation/cyclization of 1,6‐enynes with sulfonyl chlorides was reported by He group [85] . Mechanistic studies implied that a sulfonyl radical was involved in this reaction.…”

Section: Sulfonylation Reaction Using Sodium Sulfinatesmentioning

confidence: 96%

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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“…In 2020, we described a visible light‐initiated cyclization of 1,6‐enynes with sulfonyl chlorides to synthesize 2‐pyrrolidones at room temperature for the first time (Scheme 23). [37] Compared to existing methods, this method featured mild reaction conditions, such as the ability to be run in open‐air at room temperature as well as only requiring 2‐MeTHF as the solvent and visible light, all of which made this a green method.…”

Section: Radical Cyclization Of 1n‐enynesmentioning

confidence: 99%

Radical Cyclization of 1,n‐Enynes and 1,n‐Dienes for the Synthesis of 2‐Pyrrolidone

Jiang

et al. 2021

Chemistry An Asian Journal

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2‐Pyrrolidones have aroused enormous interest as a useful structural moiety in drug discovery; however, not only does their syntheses suffer from low selectivity and yield, but also it requires high catalyst loadings. The radical cyclization of 1,n‐enynes and 1,n‐dienes has demonstrated to be an attractive method for the synthesis of 2‐pyrrolidones due to its mild reaction conditions, fewer steps, higher atom economy, excellent functional group compatibility, and high regioselectivity. Furthermore, radical receptors with unsaturated bonds (i. e. 1,n‐enynes and 1,n‐dienes) play a crucial role in realizing radical cyclization because of the ability to selectively introduce one or more radical sources. In this review, we discuss representative examples of methods involving the radical cyclization of 1,n‐enynes and 1,n‐dienes published in the last five years and discuss each prominent reaction design and mechanism, providing favorable tools for the synthesis of valuable 2‐pyrrolidone for a variety of applications.

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Visible-light-initiated regioselective sulfonylation/cyclization of 1,6-enynes under photocatalyst- and additive-free conditions

Abstract: Without employing a photocatalyst or additive, a strategy has been developed for the visible-light-initiated regioselective sulfonylation/cyclization of 1,6-enynes in 2-methylTHF from sulfonyl chlorides under open-air conditions at room temperature.

Cited by 119 publications

References 64 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

Radical Cyclization of 1,n‐Enynes and 1,n‐Dienes for the Synthesis of 2‐Pyrrolidone

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