N-bromosuccinimide: direct oxidation of aldehydes to acid bromides

Cheung, Yak-Fa

doi:10.1016/s0040-4039(01)95530-3

“…It is pertinent to mention here that mild halogenic oxidants like hypochlorites, [14,52,53] chlorites [54,55] and NBS [56,57] 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.…”

Section: Oxidation Of Aldehydes and Alcoholsmentioning

confidence: 99%

Cu(II) bromide catalyzed oxidation of aldehydes and alcohols

Das

¹

,

Chakraborty

²

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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“…It is pertinent to mention here that mild halogenic oxidants like hypochlorites, 14,50,51 chlorites 52,53 and NBS 54,55 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.…”

Section: Oxidation Of Aldehydes and Alcoholsmentioning

confidence: 99%

Ceric Ammonium Nitrate Catalyzed Oxidation of Aldehydes and Alcohols

Gowda

¹

,

Chakraborty

²

2011

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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 amounts of ceric ammonium nitrate [Ce(NH 4 ) 2 (NO 3 ) 6 ] (CAN) under room temperature conditions. 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. 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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“…It is pertinent to mention here that mild halogenic oxidants like hypochlorites [14,48,49], chlorites [50,51] and NBS [52,53] are not suitable for substrates with electron rich aromatic rings, olefinic bonds and secondary hydroxyl groups.…”

Section: Resultsmentioning

confidence: 99%

La<sub>2</sub>O<sub>3</sub> Catalyzed Oxidation of Alcohols

Gowda¹,

Chakraborty

²

2011

IJOC

5

0

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A variety of aromatic, aliphatic and conjugated alcohols were transformed to the corresponding carboxylic acids and ketones with a quantitative conversion in high yields with 70% t-BuOOH solution is water in the presence of catalytic amounts of La 2 O 3 . 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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N-bromosuccinimide: direct oxidation of aldehydes to acid bromides

Cited by 40 publications

References 13 publications

Cu(II) bromide catalyzed oxidation of aldehydes and alcohols

Cu(II) bromide catalyzed oxidation of aldehydes and alcohols

Ceric Ammonium Nitrate Catalyzed Oxidation of Aldehydes and Alcohols

La<sub>2</sub>O<sub>3</sub> Catalyzed Oxidation of Alcohols

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N-bromosuccinimide: direct oxidation of aldehydes to acid bromides

Cited by 40 publications

References 13 publications

Cu(II) bromide catalyzed oxidation of aldehydes and alcohols

Cu(II) bromide catalyzed oxidation of aldehydes and alcohols

Ceric Ammonium Nitrate Catalyzed Oxidation of Aldehydes and Alcohols

La&lt;sub&gt;2&lt;/sub&gt;O&lt;sub&gt;3&lt;/sub&gt; Catalyzed Oxidation of Alcohols

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La<sub>2</sub>O<sub>3</sub> Catalyzed Oxidation of Alcohols