Recent advances in the synthesis and applications of β-keto sulfones: new prospects for the synthesis of β-keto thiosulfones

Reddy, Raju Jannapu; Kumari, Arram Haritha; Kumar, Jangam Jagadesh

doi:10.1039/d1ob00111f

Cited by 54 publications

(12 citation statements)

References 129 publications

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“…β-Ketosulfones are key structural skeletons in many bioactive molecules, and their synthetic methods developed so far are predominantly through homogeneous catalysis. , For example, the photoinduced oxysulfonylation of readily available alkynes with sulfonylhydrazides could be achieved with 2 mol % Ru(bpy) 3 Cl 2 as the photocatalyst . Mechanistic studies suggested that the vinyl radical is the key intermediate which traps molecular oxygen during the reaction.…”

Section: Resultsmentioning

confidence: 99%

Building a Pyrazole–Benzothiadiazole–Pyrazole Photosensitizer into Metal–Organic Frameworks for Photocatalytic Aerobic Oxidation

et al. 2021

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Charge separation plays a crucial role in regulating photochemical properties and therefore warrants consideration in designing photocatalysts. Metal–organic frameworks (MOFs) are emerging as promising candidates for heterogeneous photocatalysis due to their structural designability and tunability of photon absorption. Herein, we report the design of a pyrazole–benzothiadiazole–pyrazole organic molecule bearing a donor–acceptor–donor conjugated π-system for fast charge separation. Further attempts to integrate such a photosensitizer into MOFs afford a more effective heterogeneous photocatalyst (JNU-204). Under visible-light irradiation, three aerobic oxidation reactions involving different oxygenation pathways were achieved on JNU-204. Recycling experiments were conducted to demonstrate the stability and reusability of JNU-204 as a robust heterogeneous photocatalyst. Furthermore, we illustrate its applications in the facile synthesis of pyrrolo[2,1-a]isoquinoline-containing heterocycles, core skeletons of a family of marine natural products. JNU-204 is an exemplary MOF platform with good photon absorption, suitable band gap, fast charge separation, and extraordinary chemical stability for proceeding with aerobic oxidation reactions under visible-light irradiation.

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Section: Resultsmentioning

confidence: 99%

Building a Pyrazole–Benzothiadiazole–Pyrazole Photosensitizer into Metal–Organic Frameworks for Photocatalytic Aerobic Oxidation

et al. 2021

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“…Among sulfone-type compounds, β-keto-sulfones are a class of valuable chemical intermediates. 60 In 2020, the Xu group reported the oxysulfonylation of alkenes toward β-ketosulfones ( 35 ) using sulfonyl hydrazides ( 33 ) and styrenes ( 34 ) with an electrochemical method ( Scheme 6 ). 61 To obtain the desired products, an undivided cell equipped with an RVC anode and a Pt cathode was employed.…”

Section: Sulfonylation Of Alkenes and Alkynesmentioning

confidence: 99%

The Application of Sulfonyl Hydrazides in Electrosynthesis: A Review of Recent Studies

2022

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Sulfonyl hydrazides are viewed as alternatives to sulfinic acids and their salts or sulfonyl halides, which are broadly used in organic synthesis or work as active pharmaceutical substances. Generally, sulfonyl hydrazides are considered good building blocks and show powerful value in a diverse range of reactions to construct C–S bonds or C–C bonds, and even C–N bonds as sulfur, carbon, or nitrogen sources, respectively. As a profound synthetic tool, the electrosynthesis method was recently used to achieve efficient and green applications of sulfonyl hydrazides. Interestingly, many unique and novel electrochemical syntheses using sulfonyl hydrazides as radical precursors have been developed, including cascade reactions, functionalization of heterocycles, as well as a continuous flow method combining with electrochemical synthesis since 2017. Accordingly, it is necessary to specifically summarize the recent developments of electrosynthesis with only sulfonyl hydrazides as radical precursors to more deeply understand and better design novel electrochemical synthesis reactions. Herein, electrosynthesis research using sulfonyl hydrazides as radical precursors since 2017 is reviewed in detail based on the chemical structures of products and reaction mechanisms.

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“…The general approach to the synthesis of β-ketosulfones is the nucleophilic substitution reaction of sodium sulfonates with α-haloketone [20][21][22]. One representative method for the preparation of β-ketosulfones involves Cu-catalyzed direct C-S cross-coupling of various oxime acetates with sodium sulfinates to construct a C(sp 3 )-S bond reaction [23][24][25][26][27][28][29][30][31][32][33][34][35][36]. Alternatively, various β-ketosulfones can be prepared through the Cu-catalyzed direct C-S coupling reaction of substituted alkenes with various sulfonylhydrazides under an oxygen atmosphere.…”

Section: Introductionmentioning

confidence: 99%

Heterogeneous Chitosan@copper Catalyzed Selective C(sp3)–H Sulfonylation of Ketone Hydrazones with Sodium Sulfinates: Direct Access to β-Ketosulfones

et al. 2023

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The exploration of inexpensive and stable heterogeneous catalysts for C–S coupling reactions remains a challenging issue. Herein, we successfully prepared a new biomass-derived copper catalyst and applied it to the selective C(sp3)–H-directed sulfonylation of ketone hydrazones with commercial sodium sulfinates. The catalyst was characterized using different spectroscopic and microscopic techniques. Importantly, the prepared biomass-supported Cu catalyst catalyzed the C–S coupling reaction with considerably high activity. A variety of aryl and alkyl sulfinates were converted to the corresponding sulfones with good yields. In particular, the heterogeneous catalyst could be recovered easily after the synthesis and consecutively used at least five times with no appreciable decrease in the catalytic activity. Lastly, the copper catalyst is expected to have further applications in organic reactions catalyzed by Cu/CuO2.

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Recent advances in the synthesis and applications of β-keto sulfones: new prospects for the synthesis of β-keto thiosulfones

Abstract: The review mainly focuses on the recent developments in preparing β-keto sulfones and their enormous synthetic applications. New prospects for the synthesis of β-keto thiosulfones have also been highlighted. Over...

Cited by 54 publications

References 129 publications

Building a Pyrazole–Benzothiadiazole–Pyrazole Photosensitizer into Metal–Organic Frameworks for Photocatalytic Aerobic Oxidation

Building a Pyrazole–Benzothiadiazole–Pyrazole Photosensitizer into Metal–Organic Frameworks for Photocatalytic Aerobic Oxidation

The Application of Sulfonyl Hydrazides in Electrosynthesis: A Review of Recent Studies

Heterogeneous Chitosan@copper Catalyzed Selective C(sp3)–H Sulfonylation of Ketone Hydrazones with Sodium Sulfinates: Direct Access to β-Ketosulfones

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