A simple method for the oxidation of primary alcohols with o-iodoxybenzoic acid (IBX) in the presence of acetic acid

Lin, Cheng‐Kun; Lu, Ting‐Jang

doi:10.1016/j.tet.2010.10.053

Cited by 33 publications

(20 citation statements)

References 54 publications

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“…203 A similar catalytic effect was obtained when the same reaction was conducted in the presence of acetic acid. 219 The catalytic role of CB8 is not entirely understood in this case. Reddy et al studied a series of known reactions mediated by molecular halogens (iodine and bromine) and their solid-state CB6 complexes.…”

Section: Cb6-catalyzed 13-dipolar Cycloadditionsmentioning

confidence: 99%

Cucurbiturils: from synthesis to high-affinity binding and catalysis

2015

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In the wide area of supramolecular chemistry, cucurbit[n]urils (CBn) present themselves as a young family of molecular containers, able to form stable complexes with various guests, including drug molecules, amino acids and peptides, saccharides, dyes, hydrocarbons, perfluorinated hydrocarbons, and even high molecular weight guests such as proteins (e.g., human insulin). Since the discovery of the first CBn, CB6, the field has seen tremendous growth with respect to the synthesis of new homologues and derivatives, the discovery of record binding affinities of guest molecules in their hydrophobic cavity, and associated applications ranging from sensing to drug delivery. In this review, we discuss in detail the fundamental properties of CBn homologues and their cyclic derivatives with a focus on their synthesis and their applications in catalysis.

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Section: Cb6-catalyzed 13-dipolar Cycloadditionsmentioning

confidence: 99%

Cucurbiturils: from synthesis to high-affinity binding and catalysis

2015

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“…1 Benzaldehyde (2a). 27 The title compound was afforded as a colourless oil (52 mg, 99%) using general procedure B (from benzyl alcohol, 3a). Alternatively, the title compound (42 mg, 80%) was prepared using general procedure B (from benzyl acetate, 1a).…”

Section: Spectroscopic Datamentioning

confidence: 99%

Selective C–H bond electro-oxidation of benzylic acetates and alcohols to benzaldehydes

Barone

Jones

2017

Org. Biomol. Chem.

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A chemical oxidant-free and mediator-free, direct electro-oxidation of both benzylic alcohols and benzylic esters are reported. The scope of the reaction is explored as a function of both steric and electronic effects. Expansion of the scope to non-benzylic and heteroaryl substrates is investigated. Functionalisation of esters and alcohols selectively to the aldehyde oxidation level using a traceless electron approach is reported.

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“…A more hindered benzyl alcohol, 2-bromo-1-phenyl-1-ethanol (2g) was also successfully oxidised to the desired product, phenaryl bromide 3g, which is a powerful lachrymator 24 (entry 7). Furthermore, benzyl cyclic ketones were also obtained in high yields (entries [8][9][10][11]). An important photoprobe 25 , benzophenone could also be efficiently synthesised through our protocol (entry 12).…”

Section: Resultsmentioning

confidence: 99%

2-Iodoxybenzenesulfonic Acid-Catalysed oxidation of Primary and Secondary Alcohols with Oxone in Cetyl Trimethylammonium Bromide Micelles at Room Temperature

Liu

Wang

2014

Journal of Chemical Research

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A mild and green protocol for alcohol oxidation using 2-iodoxybenzene sulfonic acid/oxone at room temperature in CTAB micelles has been developed. Typically, secondary benzyl alcohols were oxidised to ketones and primary benzyl alcohols to aldehydes in good yields in 2 h. Under harsher conditions (100 °C/24 h), aliphatic alcohols were oxidised to ketones or organic acids in moderate to high yields.

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A simple method for the oxidation of primary alcohols with o-iodoxybenzoic acid (IBX) in the presence of acetic acid

Cited by 33 publications

References 54 publications

Cucurbiturils: from synthesis to high-affinity binding and catalysis

Cucurbiturils: from synthesis to high-affinity binding and catalysis

Selective C–H bond electro-oxidation of benzylic acetates and alcohols to benzaldehydes

2-Iodoxybenzenesulfonic Acid-Catalysed oxidation of Primary and Secondary Alcohols with Oxone in Cetyl Trimethylammonium Bromide Micelles at Room Temperature

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