Cooperative Dehydrogenation of N‐Heterocycles Using a Carbon Nanotube–Rhodium Nanohybrid

Jawale, Dhanaji V.; Gravel, Edmond; Shah, Nimesh; Dauvois, V.; Li, Haiyan; Namboothiri, Irishi N. N.; Doris, Eric

doi:10.1002/chem.201500148

Cited by 94 publications

(49 citation statements)

References 43 publications

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“…122 Since poor activity was observed upon replacing Q4 red with 2-tert-butylhydroquinone (TBHQ), they believed the catalytic activity of hydroquinone was affected by the geometrical effects of the substituent groups, and proposed the addition−elimination mechanism was preferred in this system.…”

Section: Scheme 41 Proposed Reaction Mechanisms Mediated By Q4 Red /Pmentioning

confidence: 99%

Recent Advances in Aerobic Oxidation of Alcohols and Amines to Imines

2015

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Imines as valuable intermediates are widely applied in pharmaceutical syntheses and organic transformation. However, the traditional imine synthesis involves unstable aldehydes, dehydrating agents and Lewis acid catalysts. The topic of review is focused on three new approaches, namely, the cross-coupling of alcohols with amines, the self-coupling of primarily amines, and the oxidative dehydrogenation of secondary amines, utilizing much more readily available starting materials and green oxidant (O 2 /air) to furnish the imine products. The related catalysts are classified into metal, metal-free, photo-, and bioinspired catalysts. Particular emphasis is placed on the high-active, low-cost, and versatile catalysts; key factors that affect the catalytic activity, and reaction mechanisms are also highlighted.

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Section: Scheme 41 Proposed Reaction Mechanisms Mediated By Q4 Red /Pmentioning

confidence: 99%

Recent Advances in Aerobic Oxidation of Alcohols and Amines to Imines

2015

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“…Similar reactivity was reported recently by Doris and coworkers, who showed that Rh nanoparticles supported on carbon nanotubes (Rh-CNT) are efficient co-catalysts with 4- tert -butyl- o -quinone in the aerobic dehydrogenations of N -heterocycles. [115] …”

Section: Bioinspired O-quinone-catalyzed Oxidation Of Aminesmentioning

confidence: 99%

Quinone‐Catalyzed Selective Oxidation of Organic Molecules

2015

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Lead In Quinones are common stoichiometric reagents in organic chemistry. High potential para-quinones, such as DDQ and chloranil, are widely used and typically promote hydride abstraction. In recent years, many catalytic applications of these methods have been achieved by using transition metals, electrochemistry or O2 to regenerate the oxidized quinone in situ. Complementary studies have led to the development of a different class of quinones that resemble the ortho-quinone cofactors in Copper Amine Oxidases and mediate efficient and selective aerobic and/or electrochemical dehydrogenation of amines. The latter reactions typically proceed via electrophilic transamination and/or addition-elimination reaction mechanisms, rather than hydride abstraction pathways. The collective observations show that the quinone structure has a significant influence on the reaction mechanism and have important implications for the development of new quinone reagents and quinone-catalyzed transformations.

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“…The same research groups have reported another nanocatalyst in which Au NPs have been replaced by rhodium nanoparticles, 85‐Rh , and also this material showed a high versatility being able to promote selective aerobic mild oxidative processes on different classes of substrates such as hydroquinones, hydroxy‐lamines, silanes, hydrazines and thiols at room temperature . Nanohybrid 85‐Rh efficiently worked in the direct and co‐catalytic oxidation of hydroxylamines to the corresponding nitrones, being the catalytic system recycled 3 times and, along with tert ‐butylcatechol, in the cooperative dehydrogenation of several N ‐heterocycles and secondary amines …”

Section: Carbon Nanotubes‐based Catalystsmentioning

confidence: 99%

Modified Nanocarbons for Catalysis

2018

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Nanocarbons represent useful scaffolds in the preparation of last generation nanostructured catalysts, and their chemical functionalization through covalent or non‐covalent modification is becoming an important tool for introducing well‐distributed anchoring points and, in the meantime, could be the first step toward the assembling of hybrid nanostructured materials with a hierarchical order. In this Review are reported synthesis and catalytic applications of chemically modified nanocarbons such as fullerene, carbon nanotubes, graphene, nanohorns and nanodiamonds in organocatalytic and metal‐based (metal nanoparticles, organometallic complexes) reactions, covering major chemical reactions encompassing, the oxidation of alcohols, aldehydes, olefins, and silanes, hydrogenation reactions of aldehydes, ketones, and alkenes, dehydrogenative coupling of silanes, C−C coupling reactions, epoxidation of alkenes, CO2 fixation into cyclic carbonates, and asymmetric reactions, among others.

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Cooperative Dehydrogenation of N‐Heterocycles Using a Carbon Nanotube–Rhodium Nanohybrid

Cited by 94 publications

References 43 publications

Recent Advances in Aerobic Oxidation of Alcohols and Amines to Imines

Recent Advances in Aerobic Oxidation of Alcohols and Amines to Imines

Quinone‐Catalyzed Selective Oxidation of Organic Molecules

Modified Nanocarbons for Catalysis

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