3‐Methyl‐4‐oxa‐5‐azahomoadamantane: Alkoxyamine‐Type Organocatalyst for Alcohol Oxidation

Sasano, Yusuke; Murakami, Keiichi; Nishiyama, Tomohiro; Kwon, Eunsang; Iwabuchi, Yoshiharu

doi:10.1002/anie.201307144

Cited by 16 publications

(12 citation statements)

References 29 publications

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“…[34] This method was based on prior work utilizing the same family of precatalysts for simple oxidations and the kinetic resolution of activated alcohols. [35] On the basis of careful spectroscopic analysis and independent isolation experiments, the active catalytic species was identified as a pair of chlorinated oxoammonium ions ( 25a and 25b ) generated from the reaction of 24 with trichloroisocyanuric acid (TCICA).…”

Section: Catalyst–catalyst Cation–π Interactionsmentioning

confidence: 99%

The Cation–π Interaction in Small‐Molecule Catalysis

2016

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Catalysis by small molecules (≤ 1000 Da, 10−9 m) capable of binding and activating substrates via attractive, noncovalent interactions has emerged as an important approach in organic and organometallic chemistry. While the canonical noncovalent interactions—including hydrogen-bonding, ion-pairing, and π-stacking—have become mainstays of catalyst design, the cation–π interaction has been comparatively underutilized in this context since its discovery in the 1980s. However, like a hydrogen bond, the cation–π interaction exhibits a typical binding affinity of several kcal/mol with substantial directionality. These properties render it attractive as a design element for the development of small-molecule catalysts, and in recent years, the catalysis community has begun to take advantage of these features, drawing inspiration from pioneering research in molecular recognition and structural biology. This review surveys the burgeoning application of the cation–π interaction in catalysis.

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Section: Catalyst–catalyst Cation–π Interactionsmentioning

confidence: 99%

The Cation–π Interaction in Small‐Molecule Catalysis

2016

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“…On the base of previous literatures reported, [40–42] a plausible reaction mechanism for the 1‐Me‐AZADO/MPNs catalyzed oxidation of alcohols was proposed and illustrated in scheme 2. An initial one electron oxidation of the supported catalyst affords oxoammonium cation ( A ) in the presence of NaClO and KBr.…”

Section: Resultsmentioning

confidence: 99%

“…The results suggested that the recyclable performance of the catalyst was strongly dependent on the activity of substrate, which might be similar to that of the previous report. [34] On the base of previous literatures reported, [40][41][42] a plausible reaction mechanism for the 1-Me-AZADO/MPNs catalyzed oxidation of alcohols was proposed and illustrated in scheme…”

Section: Resultsmentioning

confidence: 99%

Heterogeneous Catalysis for Oxidation of Alcohol via 1‐Methyl‐2‐azaadamanane N‐oxyl Immobilized on Magnetic Polystyrene Nanosphere

Guo

Wang

et al. 2022

ChemistrySelect

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Heterogeneous selective oxidation of alcohol to carbonyl compounds with stable organic nitroxyl radicals is highly attractive yet grand challenging. Described herein is a highly promising heterogeneous strategy for this reaction in which a catalytic amount of 1-methyl-2-azaadamanane N-oxyl immobilized on magnetic polystyrene nanosphere (1-Me-AZADO/ MPNs) was used and a series of carbonyl compounds were obtained from various alcohols in 73-99 % isolated yields and high selectivity (> 99 %) under Anelli conditions, thus offering a greener and more convenient methods in the synthesis of carbonyl compounds. The attractive features of convenient magnetic separation (within seconds), good recyclability (up to 20 runs) and fast reaction rates (5-20 min) were very efficient to improve the utility of azaadamantane-type-nitroxyl radicals in the oxygenation.

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“…[17][18][19] Unfortunately, the method was faded away, since bromine was a toxic, dangerous, and environmentally harmful reagent. In recent years, several oxidation systems with the assistance of bromide have been developed.…”

Section: Introductionmentioning

confidence: 98%