Oxidation of Vicinal Diols to α‐Hydroxy Ketones with H(2)O(2) and a Simple Manganese Catalyst

α‐Hydroxy ketones are valuable synthons in organic chemistry. Here we show that oxidation of vic‐diols to α‐hydroxy ketones with H(2)O(2) can be achieved with an in situ prepared catalyst based on manganese salts and pyridine‐2‐carboxylic acid. Furthermore the same catalyst is effective in alkene ep...

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Autores principales: Mecozzi, Francesco, Dong, Jia Jia, Saisaha, Pattama, Browne, Wesley R.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2017
Materias:
Full Papers
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5767754/
https://www.ncbi.nlm.nih.gov/pubmed/29398954
http://dx.doi.org/10.1002/ejoc.201701314
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author Mecozzi, Francesco
Dong, Jia Jia
Saisaha, Pattama
Browne, Wesley R.
author_facet Mecozzi, Francesco
Dong, Jia Jia
Saisaha, Pattama
Browne, Wesley R.
author_sort Mecozzi, Francesco
collection PubMed
description α‐Hydroxy ketones are valuable synthons in organic chemistry. Here we show that oxidation of vic‐diols to α‐hydroxy ketones with H(2)O(2) can be achieved with an in situ prepared catalyst based on manganese salts and pyridine‐2‐carboxylic acid. Furthermore the same catalyst is effective in alkene epoxidation, and it is shown that alkene oxidation with the Mn(II) catalyst and H(2)O(2) followed by Lewis acid ring opening of the epoxide and subsequent oxidation of the alkene to α‐hydroxy ketones can be achieved under mild (ambient) conditions.
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spelling pubmed-57677542018-02-01 Oxidation of Vicinal Diols to α‐Hydroxy Ketones with H(2)O(2) and a Simple Manganese Catalyst Mecozzi, Francesco Dong, Jia Jia Saisaha, Pattama Browne, Wesley R. European J Org Chem Full Papers α‐Hydroxy ketones are valuable synthons in organic chemistry. Here we show that oxidation of vic‐diols to α‐hydroxy ketones with H(2)O(2) can be achieved with an in situ prepared catalyst based on manganese salts and pyridine‐2‐carboxylic acid. Furthermore the same catalyst is effective in alkene epoxidation, and it is shown that alkene oxidation with the Mn(II) catalyst and H(2)O(2) followed by Lewis acid ring opening of the epoxide and subsequent oxidation of the alkene to α‐hydroxy ketones can be achieved under mild (ambient) conditions. John Wiley and Sons Inc. 2017-12-11 2017-12-15 /pmc/articles/PMC5767754/ /pubmed/29398954 http://dx.doi.org/10.1002/ejoc.201701314 Text en © 2017 The Authors. Published by Wiley‐VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution‐NonCommercial (http://creativecommons.org/licenses/by-nc/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited and is not used for commercial purposes.
spellingShingle Full Papers
Mecozzi, Francesco
Dong, Jia Jia
Saisaha, Pattama
Browne, Wesley R.
Oxidation of Vicinal Diols to α‐Hydroxy Ketones with H(2)O(2) and a Simple Manganese Catalyst
title Oxidation of Vicinal Diols to α‐Hydroxy Ketones with H(2)O(2) and a Simple Manganese Catalyst
title_full Oxidation of Vicinal Diols to α‐Hydroxy Ketones with H(2)O(2) and a Simple Manganese Catalyst
title_fullStr Oxidation of Vicinal Diols to α‐Hydroxy Ketones with H(2)O(2) and a Simple Manganese Catalyst
title_full_unstemmed Oxidation of Vicinal Diols to α‐Hydroxy Ketones with H(2)O(2) and a Simple Manganese Catalyst
title_short Oxidation of Vicinal Diols to α‐Hydroxy Ketones with H(2)O(2) and a Simple Manganese Catalyst
title_sort oxidation of vicinal diols to α‐hydroxy ketones with h(2)o(2) and a simple manganese catalyst
topic Full Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5767754/
https://www.ncbi.nlm.nih.gov/pubmed/29398954
http://dx.doi.org/10.1002/ejoc.201701314
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