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Issue 11, 2016
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Manganese-catalysed hydroperoxidation of carbon–carbon double bonds using molecular oxygen present in air and hydroxylamine under ambient conditions

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Abstract

A highly efficient manganese-catalysed hydroperoxidation of carbon–carbon double bonds of enynes as well as styrene derivatives using N-hydroxyphthalimide, N-hydroxybenzotriazole or N-hydroxysuccinimide was developed. This reaction proceeded at room temperature through the direct incorporation of molecular oxygen present in air. The required catalytic loading of manganese(III) acetylacetonate is extremely low (generally 0.02–0.5 mol%, and a minimum of 0.001 mol%).

Graphical abstract: Manganese-catalysed hydroperoxidation of carbon–carbon double bonds using molecular oxygen present in air and hydroxylamine under ambient conditions

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Supplementary files

Article information


Submitted
30 Jun 2016
Accepted
22 Aug 2016
First published
23 Aug 2016

Org. Chem. Front., 2016,3, 1420-1424
Article type
Research Article
Author version available

Manganese-catalysed hydroperoxidation of carbon–carbon double bonds using molecular oxygen present in air and hydroxylamine under ambient conditions

D. Yamamoto, M. Soga, H. Ansai and K. Makino, Org. Chem. Front., 2016, 3, 1420
DOI: 10.1039/C6QO00318D

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