A recyclable Amberlyst-15-catalyzed three-component reaction in water to synthesize diarylmethyl sulfones

Kuchukulla, Ratnakar Reddy; Li, Fuhai; He, Ze; Zhou, Lihong; Zeng, Qingle

doi:10.1039/c9gc02774b

Cited by 23 publications

(17 citation statements)

References 29 publications

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“…In view of this and as our ongoing research in organosulfur chemistry, here we report a Brønsted acid‐catalyzed metal‐free three‐component reaction in water to obtain aryl(chalcogen‐heteroaryl)methyl sulfones with broad substrate scope (Scheme ‐ 1e), and product transformation into other valuable molecules such as bactericidal agent analogue via new reactions are also demonstrated.…”

Section: Methodsmentioning

confidence: 99%

Synthesis of Aryl(chalcogen‐heteroaryl)methyl Sulfones via Sulfuric Acid‐Promoted Three‐Component Reaction in Water

et al. 2020

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A facile and efficient three‐component reaction in the presence of Brønsted acid in water was developed to synthesize aryl(chalcogen‐heteroaryl)methyl sulfones in good to very high yields with broad substrate scope. Our protocol is eco‐friendly, metal free, and atom economic. The sulfone products may be efficiently transformed into a bactericidal agent analogue and an aryl heteroaryl ketone.

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Section: Methodsmentioning

confidence: 99%

Synthesis of Aryl(chalcogen‐heteroaryl)methyl Sulfones via Sulfuric Acid‐Promoted Three‐Component Reaction in Water

et al. 2020

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“…Similar products were also prepared by three-component reaction of aldehydes, sodium sulfinates, and di-or trimethoxybenzenes in the presence of Amberlyst-15 in water. [184]…”

Section: (Scheme 131bmentioning

confidence: 99%

“…The reaction between p ‐quinone methides 337 and sulfonyl hydrazides 338 [182] or sodium sulfinates 339 [183] resulted in substituted 4‐(sulfonylmethyl)phenols 340 in high yields (Scheme 147). Similar products were also prepared by three‐component reaction of aldehydes, sodium sulfinates, and di‐ or trimethoxybenzenes in the presence of Amberlyst‐15 in water [184] …”

Section: Sulfonylation Of Carbocyclesmentioning

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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“…It is very interesting that the reaction at room temperature gave diaryl sulfones as a product, but the reaction at 60 • C provided aryl heteroarenes as the product. In 2019, the Deng group developed a three-component reaction for the preparation of diarylmethyl sulfones from aldehydes, arenes, and sodium sulfinates via tandem C-C/C-S bond formation (Scheme 54) [76]. The reaction proceeded at 60 • C in water in the presence of ion exchange resin amberlyst 15.…”

Section: Scheme 50mentioning

confidence: 99%

Recent Advances in the Synthesis of Sulfides, Sulfoxides and Sulfones via C-S Bond Construction from Non-Halide Substrates

Zhang

Ding

et al. 2020

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The construction of a C-S bond is a powerful strategy for the synthesis of sulfur containing compounds including sulfides, sulfoxides, and sulfones. Recent methodological developments have revealed lots of novel protocols for C-S bond formation, providing easy access to sulfur containing compounds. Unlike traditional Ullmann typed C-S coupling reaction, the recently developed reactions frequently use non-halide compounds, such as diazo compounds and simple arenes/alkanes instead of aryl halides as substrates. On the other hand, novel C-S coupling reaction pathways involving thiyl radicals have emerged as an important strategy to construct C-S bonds. In this review, we focus on the recent advances on the synthesis of sulfides, sulfoxides, and sulfones from non-halide substrates involving C-S bond construction.

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A recyclable Amberlyst-15-catalyzed three-component reaction in water to synthesize diarylmethyl sulfones

Abstract: A recyclable Amberlyst-15-catalyzed three-component reaction in water was developed to synthesize asymmetric diarylmethyl sulfones in good to excellent yields with a wide substrate scope.

Cited by 23 publications

References 29 publications

Synthesis of Aryl(chalcogen‐heteroaryl)methyl Sulfones via Sulfuric Acid‐Promoted Three‐Component Reaction in Water

Synthesis of Aryl(chalcogen‐heteroaryl)methyl Sulfones via Sulfuric Acid‐Promoted Three‐Component Reaction in Water

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

Recent Advances in the Synthesis of Sulfides, Sulfoxides and Sulfones via C-S Bond Construction from Non-Halide Substrates

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