Exogenous-oxidant- and catalyst-free electrochemical deoxygenative C2 sulfonylation of quinoline <i>N</i>-oxides

Jiang, Minbao; Yuan, Yong; Wang, Tao; Xiong, Y.; Jun, Li; Guo, Huijiao; Lei, Aiwen

doi:10.1039/c9cc07777d

Cited by 56 publications

(57 citation statements)

References 55 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…For isoquinoline‐ N ‐oxide, formation of two regioisomers with a sulfo group at the 1 st or 3 d position in the ratio 1.1:1 was observed [206] . Electrochemical version of quinoline‐ N ‐oxides sulfonylation was also reported [207] . When sulfonyl hydrazides 373 were used as sulfonylation reagents, 2‐sulfonylated derivatives of quinolines 374 were synthesized from the corresponding N ‐oxides 372 using the I 2 /H 2 O 2 /NaOH [208] (Scheme 163a) or NaI/TBHP [209] (Scheme 163b) systems.…”

Section: Sulfonylation Of Heterocyclesmentioning

confidence: 95%

“…[206] Electrochemical version of quinoline-N-oxides sulfonylation was also reported. [207] When sulfonyl hydrazides 373 were used as sulfonylation reagents, 2-sulfonylated derivatives of quinolines 374 were synthesized from the corresponding N-oxides 372 using the I 2 /H 2 O 2 / NaOH [208] (Scheme 163a) or NaI/TBHP [209] (Scheme 163b) systems. Similar results were obtained for isoquinolines and pyridines.…”

Section: Sulfonylation Of Six-membered Heterocyclesmentioning

confidence: 99%

See 1 more Smart Citation

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

et al. 2020

View full text Add to dashboard Cite

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.

show abstract

Section: Sulfonylation Of Heterocyclesmentioning

confidence: 95%

Section: Sulfonylation Of Six-membered Heterocyclesmentioning

confidence: 99%

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

et al. 2020

View full text Add to dashboard Cite

show abstract

“…One application of this technology is exemplified by Lei's sulfonylation of quinoline N ‐oxides using sodium sulfinates via a Minisci‐type mechanism (Scheme 53). [78] Sodium sulfinates 142 act as both the sulfonylation source and the activating agent.…”

Section: Simple C2‐h‐functionalizationmentioning

confidence: 99%

Recent Advances in the Synthesis of C2‐Functionalized Pyridines and Quinolines Using N‐Oxide Chemistry

et al. 2020

View full text Add to dashboard Cite

While remarkable progress has recently been made for the direct C−H‐functionalization of azines, its application is still limited by a lack of accessible functional groups (primarily carbon‐based) and poor regioselectivity. In contrast, C2‐functionalized pyridines and quinolines can be easily synthesized by treating readily available N‐oxides with various reagents under appropriate activation conditions. This review seeks to comprehensively document the available synthetic methods for introducing functional groups at the C2 position of pyridines and quinolines. In this work, we highlight recent developments in the C2‐functionalization of pyridine and quinoline N‐oxides and address both the mechanisms and regioselectivity of the reactions. We also describe the pathways and reactive species involved in these processes and highlight a number of medically relevant nitrogen heteroaromatics.

show abstract

“…An iron (III)‐catalyzed protocol towards 2‐sulfonyl quinolines from quinoline N‐oxides and sodium sulfinates was illustrated by An group in the same year [46] . In 2019, the electrochemical deoxygenative C2 sulfonylation of quinoline N‐oxides with sodium sulfinates for the synthesis of sulfonylated quinoline derivatives was developed by Lei group [47] . Control experiments suggested that quinoline might not be a reaction intermediate.…”

Section: Sulfonylation Reaction Using Sodium Sulfinatesmentioning

confidence: 99%

“…[46] In 2019, the electrochemical deoxygenative C2 sulfonylation of quinoline N-oxides with sodium sulfinates for the synthesis of sulfonylated quinoline derivatives was developed by Lei group. [47] Control experiments suggested that quinoline might not be a reaction intermediate. Sulfonyl radical which was generated from the anodic oxidation of benzene sulfinate was proposed for this reaction (Scheme 37).…”

Section: Sulfonylation With Arenesmentioning

confidence: 99%

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

et al. 2020

View full text Add to dashboard Cite

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.

show abstract

Exogenous-oxidant- and catalyst-free electrochemical deoxygenative C2 sulfonylation of quinoline N-oxides

Abstract: By employing quinoline N-oxides as the starting materials, the electrochemical C–H sulfonylation of electron-deficient quinolines was indirectly achieved at room temperature.

Cited by 56 publications

References 55 publications

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

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

Recent Advances in the Synthesis of C2‐Functionalized Pyridines and Quinolines Using N‐Oxide Chemistry

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

Contact Info

Product

Resources

About