2‐Iodoxy‐5‐Methylbenzenesulfonic Acid‐Catalyzed Selective Oxidation of 4‐Bromobenzyl Alcohol to 4‐Bromobenzaldehyde or 4‐Bromobenzoic Acid with Oxone

Uyanik, Muhammet; Ishihara, Kazuaki; Faul, Margaret M.; Crockett, Richard

doi:10.1002/0471264229.os089.12

Cited by 4 publications

(3 citation statements)

References 15 publications

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“…Based on previous studies [ 24 , 33 , 34 , 35 , 36 , 37 ], a proposed reaction mechanism is depicted in Scheme 4 . In situ -generated IBS ( 2 ) reversibly combines with 3 to give IBS-phenol complex 10 , which serves to transfer oxygen from an iodoxy group (I V = O) to the ortho -site of the phenol through concerted intramolecular [ 2 , 3 ]-rearrangement.…”

Section: Resultsmentioning

confidence: 99%

“…We recently reported a highly efficient and chemoselective oxidation of various alcohols to carbonyl compounds such as aldehydes, carboxylic acids, and ketones with powdered Oxone ® in the presence of catalytic amounts (1–5 mol%) of 2-iodobenzenesulfonic acids ( pre -IBSes) or their sodium salts ( 1a –c ) under nonaqueous conditions ( Scheme 1 a) [ 33 , 34 , 35 , 36 ]. 2-Iodoxybenzenesulfonic acids (IBSes) 2a –c as iodine(V), which are generated in situ from 1a –c and Oxone ® , serve as the actual catalysts for the oxidations ( Scheme 1 b) [ 33 , 34 , 35 , 36 ]. According to previous theoretical calculations [ 33 ], the relatively ionic character of the intramolecular hypervalent iodine-OSO 2 bond of IBS 2a lowers the twisting barrier of the alkoxyperiodinane intermediate.…”

Section: Introductionmentioning

confidence: 99%

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IBS-Catalyzed Regioselective Oxidation of Phenols to 1,2-Quinones with Oxone®

2012

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We have developed the first example of hypervalent iodine(V)-catalyzed regioselective oxidation of phenols to o-quinones. Various phenols could be oxidized to the corresponding o-quinones in good to excellent yields using catalytic amounts of sodium salts of 2-iodobenzenesulfonic acids (pre-IBSes) and stoichiometric amounts of Oxone® as a co-oxidant under mild conditions. The reaction rate of IBS-catalyzed oxidation under nonaqueous conditions was further accelerated in the presence of an inorganic base such as potassium carbonate (K2CO3), a phase transfer catalyst such as tetrabutylammonium hydrogen sulfate (nBu4NHSO4), and a dehydrating agent such as anhydrous sodium sulfate (Na2SO4).

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

IBS-Catalyzed Regioselective Oxidation of Phenols to 1,2-Quinones with Oxone®

2012

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“…IBX) as the oxidants to prepare the unsaturated aldehydes and ketones with dimethylsulfoxide as the solvent [10a,b] . Luo and some other groups also reported related works by using hypervalent iodine reagents as the oxidants [10c–t] . Besides, Chen group developed the iodine‐catalyzed α , β ‐dehydrogenation of ketones and aldehydes (I 2 /KI/DMSO system) [10u] .…”

Section: Introductionmentioning

confidence: 99%

Transition‐Metal‐Catalyzed α,β‐Dehydrogenation of Carbonyl Compounds

Li,

Dai,

et al. 2024

Eur J Org Chem

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Abstractα,β‐Unsaturated compounds are one of the most important functional compounds. Due to their unique property and versatile utility, they usually occur as the key intermediates for the synthesis of pharmaceuticals and biological materials. Thus, their synthesis has attracted more attentions than before. The early approaches to α,β‐unsaturated compounds are mainly about transition‐metal‐free methods, such as halogenation‐dehydrohalogenation methods and strong oxidants methods (organosulfur, organoselenium, benzoquinone). Subsequently, palladium and the other transition‐metals catalyzed dehydrogenation of carbonyl compounds appeared respectively. In this review, transition‐metal‐catalyzed α,β‐dehydrogenation is discussed, which is categorized by functional groups.

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Preparation of a Key Intermediate En Route to the Anti-HIV Drug Lenacapavir

Caravez,

Hu,

Oftadeh

et al. 2024

J. Org. Chem.

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A very efficient four-step synthesis of the main fragment of Gilead’s anti-HIV drug lenacapavir is described. The route showcases a 1,2-addition to an intermediate aldehyde using an organozinc halide derived from a commercially available difluorobenzyl Grignard reagent. This sets the stage for the oxidation of the resulting secondary alcohol to the desired ketone, which relies solely on catalytic amounts of TEMPO together with NaClO as the terminal oxidant, affording the targeted ketone in 67% overall yield.

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2‐Iodoxy‐5‐Methylbenzenesulfonic Acid‐Catalyzed Selective Oxidation of 4‐Bromobenzyl Alcohol to 4‐Bromobenzaldehyde or 4‐Bromobenzoic Acid with Oxone

Cited by 4 publications

References 15 publications

IBS-Catalyzed Regioselective Oxidation of Phenols to 1,2-Quinones with Oxone®

IBS-Catalyzed Regioselective Oxidation of Phenols to 1,2-Quinones with Oxone®

Transition‐Metal‐Catalyzed α,β‐Dehydrogenation of Carbonyl Compounds

Preparation of a Key Intermediate En Route to the Anti-HIV Drug Lenacapavir

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