Oxidation of Vicinal Diols to α‐Hydroxy Ketones with H2O2 and a Simple Manganese Catalyst. Issue 46 (11th December 2017)

• Record Type: Journal Article
• Authors: Mecozzi, Francesco; Dong, Jia Jia; Saisaha, Pattama; Browne, Wesley R.
• Is Part Of: European journal of organic chemistry. Issue 46(2017)
• Page Start: 6919
• Page End: 6925
• Publication Date: 2017-12-11
• Subjects: Earth‐abundant metals -- Oxidation -- Manganese -- Hydroxyl ketone -- Homogeneous catalysis -- Hydrogen peroxide; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201701314
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : α‐Hydroxy ketones are valuable synthons in organic chemistry. Here we show that oxidation of vic ‐diols to α‐hydroxy ketones with H2 O2 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 H2 O2 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. Abstract : Oxidation of vic ‐diols to α‐hydroxy ketones with H2 O2 can be achieved with an in situ prepared catalyst based on manganese salts and pyridine‐2‐carboxylic acid, which is also effective in alkene epoxidation. Alkene oxidation with this Mn II catalyst and H2 O2 followed by Lewis acid ring opening of the epoxide and subsequent oxidation of the alkene to α‐hydroxy ketones can be achieved under mild conditions.