2004Advanced Synthesis & CatalysisRequires access

IBX‐Mediated Conversion of Primary Alcohols and Aldehydes to N‐Hydroxysuccinimide Esters

Agnes Schulze, Athanassios Giannis

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Abstract

Abstract Recently, the use of the hypervalent iodine reagent 1‐hydroxy‐1,2‐benziodoxol‐3(1H)‐one 1‐oxide (IBX) for the oxidation of primary alcohols and aldehydes to carboxylic acids was described. During the synthesis of these carboxylic acids the corresponding N‐hydroxysuccinimide esters were formed as intermediate products, but their isolation as main reaction products was not successful. We report herein a simple and very efficient method to prepare these synthetically valuable active esters.

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What this paper is about

Abstract Recently, the use of the hypervalent iodine reagent 1‐hydroxy‐1,2‐benziodoxol‐3(1H)‐one 1‐oxide (IBX) for the oxidation of primary alcohols and aldehydes to carboxylic acids was described. During the synthesis of these carboxylic acids the corresponding N‐hydroxysuccinimide esters were formed as intermediate products, but their isolation as main reaction products was not successful. We report herein a simple and very efficient method to prepare these synthetically valuable active esters.

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Available abstract

Abstract Recently, the use of the hypervalent iodine reagent 1‐hydroxy‐1,2‐benziodoxol‐3(1H)‐one 1‐oxide (IBX) for the oxidation of primary alcohols and aldehydes to carboxylic acids was described. During the synthesis of these carboxylic acids the corresponding N‐hydroxysuccinimide esters were formed as intermediate products, but their isolation as main reaction products was not successful. We report herein a simple and very efficient method to prepare these synthetically valuable active esters.

Key concepts: Chemistry, Hypervalent molecule, Primary (astronomy), Reagent, Organic chemistry, Iodine, Aldehyde, Alcohol oxidation

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