Journal
ACS CATALYSIS
Volume 2, Issue 6, Pages 1087-1096Publisher
AMER CHEMICAL SOC
DOI: 10.1021/cs3002226
Keywords
manganese; epoxidation; cis-dihydroxylation; hydrogen peroxide
Categories
Funding
- Netherlands Organization for Scientific Research (NWO) VIDI [700.57.428]
- Catchbio
- ERC [279549]
- European Research Council (ERC) [279549] Funding Source: European Research Council (ERC)
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A simple, high yielding catalytic method for the multigram scale selective epoxidation of electron-rich alkenes using near-stoichiometric H2O2 under ambient conditions is reported. The system consists of a Mn(II) salt (<0.01 mol %), pyridine-2-carboxylic acid (<0.5 mol %), and substoichiometric butanedione. High TON (up to 300 000) and TOF (up to 40 s(-1)) can be achieved for a wide range of substrates with good to excellent selectivity, remarkable functional group tolerance, and a wide solvent scope. It is shown that the formation of 3-hydroperoxy-3-hydroxybutan-2-one from butanedione, and H2O2 in situ, is central to the activity observed.
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