Carboxylic Acids

Ogliaruso, Michael A.; Wolfe, James F.

doi:10.1016/b0-08-044705-8/00177-1

Cited by 7 publications

(1 citation statement)

References 377 publications

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“…A wide variety of synthetic methodologies targeting either the construction or utilization of α,β-unsaturated carbonyl compounds have been developed due to their ubiquitous nature in organic chemistry. Two major approaches have been utilized in constructing such functional groups: (1) concomitant formation during synthetic construction of a molecule (for example via aldol condensation or Wittig-type reactions) or (2) dehydrogenation of a previously established carbonyl compound. , Although the first approach is usually more efficient, the second approach is more important, as it provides the only option for regioselective introduction of unsaturation to previously established carbonyl compounds. Typically, the second approach involves deprotonation α to the carbonyl group to generate an enolate, which is then condensed with a variety of functional groups that can act as a leaving group in a subsequent elimination reaction.…”

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confidence: 99%

New Methodology toward α,β-Unsaturated Carboxylic Acids from Saturated Acids

Tochtrop

2014

Org. Lett.

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A carefully designed three-step unsaturation of carboxylic acids is described. Briefly, carboxylic acids were converted to the trifluoromethyl ketone. Subsequent treatment with selenium dioxide followed by hydrolysis afforded α,β-unsaturated carboxylic acids. The mechanism of the reported transformation was investigated, which led us to propose a novel explanation featuring selenium dioxide assisted enolizaion of a trifluoromethyl ketone followed by β-deprotonation.

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New Methodology toward α,β-Unsaturated Carboxylic Acids from Saturated Acids

Tochtrop

2014

Org. Lett.

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Cu(II) bromide catalyzed oxidation of aldehydes and alcohols

Das

Chakraborty

2011

Applied Organom Chemis

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A variety of aromatic, aliphatic and conjugated aldehydes and alcohols were transformed to the corresponding carboxylic acids and ketones with a quantitative conversion in high yields with 70% t-BuOOH solution in water in the presence of catalytic (5 mol%) amounts of CuBr 2 under room temperature conditions. The conversion of 4-methoxybenzaldehyde to 4-methoxybenzoic acid is extremely facile in MeCN at ambient temperature in the presence of 5 mol% CuBr 2 and 2 equiv. 70% t-BuOOH (water) as the oxidant. Oxidation with t-BuOOH (water) alone in MeCN was found to be negligible. The scope of our catalytic system is applicable for a wide range of aromatic, conjugated and aliphatic substrates. These aldehydes were converted to the corresponding carboxylic acids in good isolated yields in reasonable times. It is pertinent to mention here that mild halogenic oxidants like hypochlorites, chlorites and NBS are not suitable for substrates with electron-rich aromatic rings, olefinic bonds and secondary hydroxyl groups. Substitutions at different positions on the phenyl ring do not hinder the reaction, although the reaction time is affected. Oxidation of α,β unsaturated derivatives resulted in the formation of the expected acid in good yield. In addition, the transformation of secondary alcohols to ketones is extremely facile. No recemization was observed for menthone. This method possesses a wide range of capabilities since it can be used with other functional groups which may not tolerate oxidative conditions, involves fairly simple method for work-up, exhibits chemoselectivity and proceeds under ambient conditions. The resulting products are obtained in good yields within reasonable time.

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Mohr's salt catalyzed oxidation of aldehydes with t‐BuOOH

Chakraborty

Majumder

Malik

2011

Applied Organom Chemis

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Various aromatic, aliphatic and conjugated aldehydes were transformed to the corresponding carboxylic acids with 70% t-BuOOH solution (water) in the presence of catalytic amounts (10 mol%) of Mohr's salt. This method possesses functional group compatibility, does not involve cumbersome work-up, exhibits chemoselectivity since other functional groups remain intact and proceeds under mild conditions. The resulting products are obtained in good yields within reasonable times.

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Carboxylic Acids

Cited by 7 publications

References 377 publications

New Methodology toward α,β-Unsaturated Carboxylic Acids from Saturated Acids

New Methodology toward α,β-Unsaturated Carboxylic Acids from Saturated Acids

Cu(II) bromide catalyzed oxidation of aldehydes and alcohols

Mohr's salt catalyzed oxidation of aldehydes with t‐BuOOH

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