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Dual Catalysis for the Aerobic Oxidation of Benzyl Alcohols – Nitric Acid and Fluorinated Alcohol
Author(s) -
Možina Štefan,
Stavber Stojan,
Iskra Jernej
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.201601339
Subject(s) - chemistry , catalysis , benzyl alcohol , nitric acid , alcohol oxidation , solvent , benzoic acid , alcohol , organic chemistry , selectivity , dual role , metal , oxygen , combinatorial chemistry
Benzyl alcohols were oxidized with oxygen to aldehydes in excellent yields with high selectivities at room temperature. Dual catalysis was operative with HNO 3 as the oxidant and precursor of the nitrogen oxides and with the use of 1,1,1,3,3,3‐hexafluoro‐2‐propanol as a template catalyst and solvent. Fluorinated alcohols also increased the selectivity by inhibiting further oxidation to benzoic acids. Activation of nitric acid catalyzed aerobic oxidation by the fluorinated solvent made the use of 2,2,6,6‐tetramethylpiperidin‐1‐oxyl (TEMPO) or a metal catalyst superfluous.