Visible-light-induced deoxygenative C2-sulfonylation of quinoline <i>N</i>-oxides with sulfinic acids

Xie, Long‐Yong; Fang, Tai-Gang; Tan, Jia-Xi; Zhang, Bo; Cao, Zhong; Yang, Lihua; He, Wei‐Min

doi:10.1039/c9gc01175g

Cited by 181 publications

(62 citation statements)

References 79 publications

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“…[1][2][3][4] Among the amidine compounds, N-sulfonyl amidines are of interest as they are effective in medicinal chemistry and synthesis of synthetic intermediates for drugs. [5][6][7][8][9][10][11][12] A number of N-sulfonyl amidines with medicinal and biochemical applications are shown in Scheme 1. These compounds are bioactive pharmacophores with inhibitors of dopamine transporter, 6 anti tumour, 7 antibone resorptive agent 8 and anti-proliferative 9 properties (Fig.…”

Section: Introductionmentioning

confidence: 99%

Transition metal- and catalyst-free one-pot green method for the synthesis of N-sulfonyl amidines via direct reaction of sulfonyl azides with amines

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Section: Introductionmentioning

confidence: 99%

Transition metal- and catalyst-free one-pot green method for the synthesis of N-sulfonyl amidines via direct reaction of sulfonyl azides with amines

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“…[212] Visible light photoredox-catalyzed sulfonylation of quinoline- N-oxides with sulfinic acids at the 2 nd position was also reported. [213] In all cases, mechanism of sulfonylation apparently involves oxidation of sulfinate/sulfonyl hydrazide into the sulfonyl radical and its addition to the electron-deficient cycle, followed by aromatization: the scheme 165 shows the presumable mechanism involving CuBr 2 . [210] The presence of a benzamide group at the 8 th position provided sulfonylation of quinolines at the 5 th position using catalytic transition metals-based systems.…”

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

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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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“…In the same year, similar reactions were realized by He group. [79] Sulfonyl radical was also proposed in their reaction mechanism (Scheme 65).…”

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

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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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Visible-light-induced deoxygenative C2-sulfonylation of quinoline N-oxides with sulfinic acids

Abstract: The first example of direct synthesis of 2-sulfonylquinolines through visible-light-induced deoxygenative C2-sulfonylation of quinoline N-oxides with organic dye as the catalyst and ambient air as the sole oxidant was developed.

Cited by 181 publications

References 79 publications

Transition metal- and catalyst-free one-pot green method for the synthesis of N-sulfonyl amidines via direct reaction of sulfonyl azides with amines

Transition metal- and catalyst-free one-pot green method for the synthesis of N-sulfonyl amidines via direct reaction of sulfonyl azides with amines

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

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

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