Graphene oxide as a carbocatalyst: the first example of a one-pot sequential dehydration–hydrothiolation of secondary aryl alcohols

Basu, Basudeb; Kundu, Samir; Sengupta, Debapriya

doi:10.1039/c3ra44712j

Cited by 34 publications

(12 citation statements)

References 23 publications

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“…These reactions encompass the oxidative hydrogen atom transfer reactions. In addition, the O-rich carbon materials have been active catalysts in various reactions (that is, nucleophilic addition of alcohol to an epoxide 22 , aldehyde acetalization or esterification 23,24 , Michael addition reactions 25,26 , F-C addition of indoles to a,bunsaturated ketones 27 and synthesis of dipyrromethane 28 , among others 29,30 ). In these studies, nearly all of the organic transformations have been focused on oxidative hydrogen atom transfer reactions or acid-catalysed reactions with heteroatommodified carbon materials (Fig.…”

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confidence: 99%

Carbon-catalysed reductive hydrogen atom transfer reactions

et al. 2015

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Generally, transition metal catalysts are essential for the reductive hydrogen atom transfer reaction, which is also known as the transfer hydrogenation reaction or the borrowinghydrogen reaction. It has been reported that graphene can be an active catalyst in ethylene and nitrobenzene reductions, but no report has described carbon-based materials as catalysts for alcohol amination via the borrowing-hydrogen reaction mechanism. Here we show the results from the preparation, characterization and catalytic performance investigation of carbon catalysts in transition metal-free borrowing-hydrogen reactions using alcohol amination and nitro compound/ketone reduction as model reactions. XPS, XRD, SEM, FT-IR and N 2 adsorption-desorption studies revealed that C ¼ O group in the carbon catalysts may be a possible catalytically active site, and high surface area is important for gaining high activity. The activity of the carbon catalyst remained unchanged after reuse. This study provides an attractive and useful methodology for a wider range of applications.

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confidence: 99%

Carbon-catalysed reductive hydrogen atom transfer reactions

et al. 2015

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“…Several experiments have since been conducted to investigate GO as a carbocatalyst. In one test, Basu and coworkers [166] produced for the first time from a mixture of secondary aryl alcohols and thiols an effective and mild one-pot GO catalyzed sequential dehydration-hydrothiolation reaction. The resultant unsymmetrical thioethers were synthesized under metalfree conditions and the catalyst could be reused for five cycles without losing any appreciable activity.…”

Section: Ionic Liquid Supported On Go As Catalystmentioning

confidence: 99%

Recent advances in the catalytic applications of GO/rGO for green organic synthesis

Sachdeva

2020

Green Processing and Synthesis

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Graphene is considered a promising catalyst candidate due to its 2D nature, single-atom thickness, zero bandgap and very high surface to volume ratio. Further, graphene oxide (GO) has been used as a catalytic support material for metal/metal oxide nanoparticles due to its tunable electrical properties. In addition, its high chemical stability and ultrahigh thermal conductivity may possibly promote high loading of catalytically active sites. This review article focuses on the recent progress in the catalytic applications of GO especially (i) as catalytic-support material (GO/reduced graphene oxide supported metal/metal oxide nanohybrids) for the green synthesis of biologically relevant molecules, (ii) for metal-free catalysis and (iii) for electrocatalysis, with special focus on graphene contribution to catalytic efficiency. The critical overview and future perspectives are also discussed.

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“…However, the generation of stoichiometric amounts of salt waste as well as low chemoselectivity values and yields under their basic conditions (high tendency for the oxidation of thiols into disulfides) are enormous disadvantages from an industrial standpoint. Thus, many catalytic methods have been developed for the direct transformation of alcohols . Most of these are atom‐efficient and generate water as the only byproduct (Figure ).…”

Section: Introductionmentioning

confidence: 99%

Highly Efficient and Chemoselective Tertiary and Secondary Benzylation of Thiols Catalyzed by Indium(III) Triflate

Kuciński

Hreczycho

2017

Eur J Org Chem

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Several examples of nucleophilic substitution reactions of compounds that have good leaving groups have been previously reported, but the direct use of simple alcohols still remains a challenge because of the poor leaving ability of the hydroxy group. Herein, an efficient and highly chemoselective method for the S‐benzylation of a wide range of aromatic and aliphatic thiols has been accomplished in the presence of catalytic amounts (0.1–0.2 mol‐%) of indium(III) triflate. Our approach is atom efficient (water is the only byproduct) and suitable to obtain the corresponding unsymmetrical thioethers in excellent yields (up to 99 %). The low loading of catalyst that are needed to obtain extraordinarily high chemoselectivities and the generality of the reaction make this approach unique.

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Graphene oxide as a carbocatalyst: the first example of a one-pot sequential dehydration–hydrothiolation of secondary aryl alcohols

Cited by 34 publications

References 23 publications

Carbon-catalysed reductive hydrogen atom transfer reactions

Carbon-catalysed reductive hydrogen atom transfer reactions

Recent advances in the catalytic applications of GO/rGO for green organic synthesis

Highly Efficient and Chemoselective Tertiary and Secondary Benzylation of Thiols Catalyzed by Indium(III) Triflate

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