Issue 84, 2014
From the journal:

RSC Advances

NHC-catalyzed one-pot oxidation and oxidative esterification of allylic alcohols using TEMPO: the effect of alcohol additives†

Ye-Won Kanga  and  Hye-Young Jang*ab  

* Corresponding authors

a Department of Energy Systems Research, Ajou University, Suwon 443-749, Korea
E-mail: hyjang2@ajou.ac.kr
Fax: +82 31 2191615
Tel: +82 31 219 2555

b Korea Carbon Capture & Sequestration R&D Center, Deajeon 305-343, Korea

Abstract

A combination of N-heterocyclic carbene (NHC) catalysts and 2,2,6,6-tetramethylpiperidine-N-oxyl (TEMPO) was proposed for the synthesis of allylic esters from allylic alcohols. The yield of one-pot conversion of allylic alcohols to esters increased when hexafluoroisopropanol (HFIP) was used. The effect of HFIP in this tandem reaction was investigated by monitoring the reaction using gas chromatographic analysis. Control experiments using oxoammonium showed that the oxidative esterification occurred via a single-electron transfer mechanism.

Graphical abstract: NHC-catalyzed one-pot oxidation and oxidative esterification of allylic alcohols using TEMPO: the effect of alcohol additives

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Article information

DOI
https://doi.org/10.1039/C4RA08133A
Article type
Communication
Submitted
05 Aug 2014
Accepted
08 Sep 2014
First published
09 Sep 2014

RSC Adv., 2014,4, 44486-44490

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NHC-catalyzed one-pot oxidation and oxidative esterification of allylic alcohols using TEMPO: the effect of alcohol additives

Y. Kang and H. Jang, RSC Adv., 2014, 4, 44486 DOI: 10.1039/C4RA08133A

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