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Oxidation of Vicinal Diols to α‐Hydroxy Ketones with H 2 O 2 and a Simple Manganese Catalyst
Author(s) -
Mecozzi Francesco,
Dong Jia Jia,
Saisaha Pattama,
Browne Wesley R.
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201701314
Subject(s) - chemistry , alkene , synthon , catalysis , epoxide , manganese , lewis acid catalysis , lewis acids and bases , pyridine , medicinal chemistry , vicinal , organic chemistry , ketone , acid catalysis , cycloalkene , polymer chemistry
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.