Symbiotic Catalysis Relay: Molecular Oxygen Activation Catalyzed by Multiple Small Molecules at Ambient Temperature and its Mechanism

Qiu, Cangbai; Jin, Liqun; Huang, Zhiliang; Tang, Zhenquan; Lei, Aiwen; Shen, Zhenlu; Sun, Nan; Mo, Weimin; Hu, Baoxiang; Hu, Xinquan

doi:10.1002/cctc.201100300

Cited by 34 publications

(10 citation statements)

References 64 publications

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“…Reactions could also proceed in good yield under air. DDQ-catalyzed aerobic alcohol oxidation has been applied to lignin depolymerization using a NO x co-catalyst system, [68,69] and other aerobic alcohol oxidation reactions have been reported in which additional cocatalysts, such as TEMPO [70a] or N -bromosuccinimide, [70b] are used in combination with DDQ and NO x .…”

Section: Ddq-catalyzed Oxidations Of Organic Substratesmentioning

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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Section: Ddq-catalyzed Oxidations Of Organic Substratesmentioning

confidence: 99%

Quinone‐Catalyzed Selective Oxidation of Organic Molecules

2015

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“…Auch an Raumluft erfolgen die Reaktionen in guter Ausbeute. Die DDQ‐katalysierte, aerobe Alkoholoxidation wurde unter Verwendung eines NO x ‐Cokatalysatorsystems zur Lignindepolymerisation eingesetzt,68, 69 und andere aerobe Alkoholoxidationsreaktionen wurden beschrieben, bei denen zusätzliche Cokatalysatoren wie 2,2,6,6‐Tetramethylpiperidinyloxyl (TEMPO)70a oder N ‐Bromsuccinimid70b in Kombination mit DDQ und NO x Verwendung fanden.…”

Section: Ddq‐katalysierte Oxidationen Organischer Substrateunclassified

Chinon‐katalysierte, selektive Oxidation organischer Moleküle

Wendlandt

Stahl

2015

Angewandte Chemie

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Chinone sind gebräuchliche, stöchiometrisch eingesetzte Reagentien in der organischen Chemie. para‐Chinone mit hohem Reduktionspotential wie DDQ und Chloranil werden verbreitet angewendet und fördern normalerweise die Hydridabstraktion. In den letzten Jahren wurden viele katalytische Anwendungen dieser Methoden entwickelt, wobei das oxidierte Chinon in situ mithilfe von Übergangsmetallen, O2 oder Elektrochemie regeneriert wird. Ergänzende Studien haben zur Entdeckung einer anderen Klasse von Chinonen geführt, die den ortho‐Chinon‐Cofaktoren in Kupfer‐Amin‐Oxidasen ähneln und effiziente und selektive aerobe und/oder elektrochemische Dehydrierungen von Aminen vermitteln. Letztgenannte Reaktionen laufen gewöhnlich über elektrophile Transaminierungs‐ und/oder Additions‐Eliminierungs‐Reaktionsmechanismen anstelle von Hydridabstraktionspfaden ab. Die gesammelten Beobachtungen zeigen, dass die Chinonstruktur einen signifikanten Einfluss auf den Reaktionsmechanismus ausübt und somit bedeutende Auswirkungen auf die Entwicklung neuer Chinonreagentien und Chinon‐katalysierter Umwandlungen hat.

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“…Hu and coworkers reported atransition-metal-free aerobic oxidation of benzylic and heteroaromatic alcohols,w ith TEMPO as an efficient substrate-selective redox catalyst (Scheme 25). [80] In this example,B r 2 and NaNO 2 are used as the co-catalysts to relay the electrons between TEMPOH and O 2 .Awide range of primary and secondary alcohols were effectively oxidized. In addition, the use of HBr/TBN or DDQ/TBN instead of Br 2 / NaNO 2 as ETMs also promotes the aerobic oxidation of alcohols to the corresponding carbonyl compounds in excellent yields.…”

Section: Angewandte Chemiementioning

confidence: 99%

Efficient Aerobic Oxidation of Organic Molecules by Multistep Electron Transfer

2021

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This Minireview presents recent important homogenous aerobic oxidative reactions which are assisted by electron transfer mediators (ETMs). Compared with direct oxidation by molecular oxygen (O2), the use of a coupled catalyst system with ETMs leads to a lower overall energy barrier via stepwise electron transfer. This cooperative catalytic process significantly facilitates the transport of electrons from the reduced form of the substrate‐selective redox catalyst (SSRCred) to O2, thereby increasing the efficiency of the aerobic oxidation. In this Minireview, we have summarized the advances accomplished in recent years in transition‐metal‐catalyzed as well as metal‐free aerobic oxidations of organic molecules in the presence of ETMs. In addition, the recent progress of photochemical and electrochemical oxidative functionalization using ETMs and O2 as the terminal oxidant is also highlighted. Furthermore, the mechanisms of these transformations are showcased.

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Symbiotic Catalysis Relay: Molecular Oxygen Activation Catalyzed by Multiple Small Molecules at Ambient Temperature and its Mechanism

Cited by 34 publications

References 64 publications

Quinone‐Catalyzed Selective Oxidation of Organic Molecules

Quinone‐Catalyzed Selective Oxidation of Organic Molecules

Chinon‐katalysierte, selektive Oxidation organischer Moleküle

Efficient Aerobic Oxidation of Organic Molecules by Multistep Electron Transfer

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