Nitrosotetrazolium‐Catalyzed Aerobic Oxidation of Alcohols to the Corresponding Carbonyl Compounds | Zendy

Matsukawa Yuta | Zendy; Hirashita Tsunehisa | Zendy; Araki Shuki | Zendy

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Nitrosotetrazolium‐Catalyzed Aerobic Oxidation of Alcohols to the Corresponding Carbonyl Compounds

Author(s) -

Matsukawa Yuta,

Hirashita Tsunehisa,

Araki Shuki

Publication year - 2018

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.201701662

Subject(s) - chemistry , alcohol oxidation , catalysis , autoxidation , organic chemistry , steric effects , tetrafluoroborate , nitroso , oxygen , catalytic cycle , photochemistry , medicinal chemistry , ionic liquid

A mesoionic‐nitrosotetrazolium‐catalyzed aerobic oxidation of alcohols is reported. In the presence of catalytic amounts of 5‐nitroso‐1,3‐diphenyltetrazolium tetrafluoroborate (5 mol‐%) and nitric acid (20 mol‐%), a wide range of alcohols are oxidized to the corresponding aldehydes and ketones in yields of 53–100 % at room temperature under ambient air or oxygen conditions. This oxidation shows a strong preference for secondary alcohols over primary alcohols; sterically hindered alcohols are also smoothly oxidized. A mechanism involving a nitroso/NO x catalytic cycle is proposed.

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