Chemoselective Aerobic Oxidation of Benzylic Alcohols to Aldehydes and Ketones

Copper(I)- and Mesoionic-Hydroxyamide-Catalyzed Chemoselective Aerobic Oxidation of Primary Benzylic Alcohols: Y. Matsukawa, T. Hirashita
Synlett 2019, DOI: 10.1055/s-0037-1611698


The use of oxygen as the oxidant is extremely attractive both from an economic and environmental perspective, as the only reaction co-product – besides the oxidized organic product – would be water. A new variant and application of this concept was recently published by Professor Tsunehisa Hirashita from the Nagoya Institute of Technology (Japan), who succeeded in achieving an efficient and chemoselective oxidation – catalyzed by copper(I) and in the presence of a mesoionic hydroxamide – to benzaldehydes and several ketones from the corresponding carbinols.

Professor Hirashita said: “Mesoionic 1,3-diphenyltetrazolium-5-hydroxyamide serves as a mediator for the aerobic selective oxidation of benzylic alcohols to the corresponding carbonyl compounds even in the presence of aliphatic alcohols.”
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