Electrochemically Induced Synthesis of Sulfonylated <i>N</i>-Unsubstituted Enamines from Vinyl Azides and Sulfonyl Hydrazides

Mulina, Olga M.; Zhironkina, Nataliya V.; Paveliev, Stanislav A.; Demchuk, D. V.; Terent’ev, Alexander O.

doi:10.1021/acs.orglett.0c00139

Cited by 61 publications

(34 citation statements)

References 77 publications

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“…Since the introduction of electron withdrawing radical, the imine radical then underwent 1,3-H migration and gave the enamine compounds. In addition, Terentevʼs group [20] also described a similar work. Very recently, our group [21] reported a radical cyclization cascade for synthesis of sulfide imidazopyridines via an imine radical intermediate under electrochemical conditions.…”

mentioning

confidence: 90%

Electrocatalytic Synthesis of gem-Bisarylthio Enamines and α-Phenylthio Ketones via a Radical Process under Mild Conditions

Pan¹,

Cheng²,

Li³

et al. 2020

Synlett

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The novel method for the synthesis of gem-bisarylthio enamines and α-phenylthio ketones was developed via the coupling of α-substituted vinyl azides with thiols in the presence of tetrabutylammonium iodide (TBAI) as a redox catalyst and electrolyte at room temperature. Electronic properties were crucial in the generated products. This protocol features metal- and oxidant-free materials, broad tolerance of substrates, and mild reaction conditions.

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mentioning

confidence: 90%

Electrocatalytic Synthesis of gem-Bisarylthio Enamines and α-Phenylthio Ketones via a Radical Process under Mild Conditions

Pan¹,

Cheng²,

Li³

et al. 2020

Synlett

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“…The sulfonylation of vinyl azides for the synthesis of sulfonylated N‐unsubstituted enamines via a chain of chemical and electrochemical transformations was disclosed by Terent'ev group [109] . Ammonium iodide can be applied as both a supporting electrolyte and a redox catalyst in this reaction.…”

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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“…Such β‐sulfonyl enamines are useful intermediates for the synthesis of β‐ketosulfones, 2 H ‐azirines, dihydropyrroles, and imines (Scheme 79). [98] β‐Sulfonyl enamines were also synthesized via sulfonylation of vinyl azides with sodium p ‐toluenesulfinate or sulfonyl hydrazides under the action of AgNO 3 [99] or electric current respectively [100] …”

Section: Sulfonylation Of Unactivated Multiple Bondsmentioning

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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Electrochemically Induced Synthesis of Sulfonylated N-Unsubstituted Enamines from Vinyl Azides and Sulfonyl Hydrazides

Cited by 61 publications

References 77 publications

Electrocatalytic Synthesis of gem-Bisarylthio Enamines and α-Phenylthio Ketones via a Radical Process under Mild Conditions

Electrocatalytic Synthesis of gem-Bisarylthio Enamines and α-Phenylthio Ketones via a Radical Process under Mild Conditions

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

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

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