The fast and efficient KI/H2O2 mediated 2-sulfonylation of indoles and N-methylpyrrole in water

Zhang, Jun; Wang, Zhong; Chen, Lingjuan; Liu, Yan; Liu, Ping; Dai, Bin

doi:10.1039/c8ra09367a

Cited by 23 publications

(10 citation statements)

References 40 publications

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“…Scheme has shown several examples of the metal‐free C−H functionalization. Barman and Liu both investigated the sulfonylation of indoles derivatives. The Maity group described the sulfenylation of imidazoheterocycles in water under heating condition, without any additive.…”

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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“…Subjecting 2-chloroquinoline-3-carbaldehyde and TosMIC to the standard reaction conditions yielded 5-(2-tosylquinolin-3-yl)oxazole ( 6a ) in 83% yield after 8 h (Scheme 2). Notably, sulfones are present in different bioactive compounds (Metzner and Thuillier, 1994; Fang et al, 2016); however, well-known sulfonylating agents include sulfonyl halides (Tocco et al, 2013; Zhang et al, 2015), sulfonyl hydrazides (Yuan et al, 2018; Zhang et al, 2018), and sodium sulfinate (Sun et al, 2017; Smith et al, 2018). A few studies used TosMIC as a sulfonyl precursor (Liu et al, 2014; Phanindrudu et al, 2016; Kadari et al, 2017).…”

Section: Resultsmentioning

confidence: 99%

Isocyanide Reactions Toward the Synthesis of 3-(Oxazol-5-yl)Quinoline-2-Carboxamides and 5-(2-Tosylquinolin-3-yl)Oxazole

et al. 2019

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A palladium-catalyzed three-component reaction between 5-(2-chloroquinolin-3-yl) oxazoles, isocyanides, and water to yield 3-(oxazol-5-yl)quinoline-2-carboxamides is described. Interestingly, sulfonylation occurred when the same reaction was performed with toluenesulfonylmethyl isocyanide (TosMIC) as an isocyanide source. The reaction with 5-(2-chloroquinolin-3-yl)oxazoles and TosMIC in the presence of Cs 2 CO 3 in DMSO afforded 5-(2-Tosylquinolin-3-yl)oxazoles. In basic media, TosMIC probably decomposed to generate Ts − species, which were replaced with Cl − . Tandem oxazole formation with subsequent sulfonylation of 2-chloroquinoline-3-carbaldehydes to form directly 5-(2-tosylquinolin-3-yl)oxazoles was also investigated.

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“…[5b,127] In 2018, the rapid and efficient KI/H 2 O 2 -mediated 2-sulfonylation of substituted indoles and N-methylpyrrole was realized by Liu group. [128] Products with good to excellent yields can be obtained within 5 min. Besides sulfonyl hydrazides, sulfinic acid and sodium sulfinate could also be applied to this sulfonylation reaction.…”

Section: Sulfonylation With Arenesmentioning

confidence: 99%

“…The sulfonylation of arenes with sulfony hydrazides has gained much progress in recent years [5b,127] . In 2018, the rapid and efficient KI/H 2 O 2 ‐mediated 2‐sulfonylation of substituted indoles and N‐methylpyrrole was realized by Liu group [128] . Products with good to excellent yields can be obtained within 5 min.…”

Section: Sulfonylation Reaction Using Sodium Sulfinatesmentioning

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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The fast and efficient KI/H₂O₂ mediated 2-sulfonylation of indoles and N-methylpyrrole in water

Abstract: The rapid and efficient KI/H2O2-mediated 2-sulfonylation of substituted indoles and N-methylpyrrole was established.

Cited by 23 publications

References 40 publications

Sulfonyl Hydrazides in Organic Synthesis: A Review of Recent Studies

Sulfonyl Hydrazides in Organic Synthesis: A Review of Recent Studies

Isocyanide Reactions Toward the Synthesis of 3-(Oxazol-5-yl)Quinoline-2-Carboxamides and 5-(2-Tosylquinolin-3-yl)Oxazole

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

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