A TEMPO‐Free Copper‐Catalyzed Aerobic Oxidation of Alcohols | Zendy

Xu Boran | Zendy; Lumb JeanPhilip | Zendy; Arndtsen Bruce A. | Zendy

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A TEMPO‐Free Copper‐Catalyzed Aerobic Oxidation of Alcohols

Author(s) -

Xu Boran,

Lumb JeanPhilip,

Arndtsen Bruce A.

Publication year - 2015

Publication title -

angewandte chemie

Language(s) - English

Resource type - Journals

eISSN - 1521-3757

pISSN - 0044-8249

DOI - 10.1002/ange.201411483

Subject(s) - alcohol oxidation , catalysis , chemistry , primary (astronomy) , alcohol , substrate (aquarium) , copper , organic chemistry , combinatorial chemistry , physics , oceanography , astronomy , geology

The copper‐catalyzed aerobic oxidation of primary and secondary alcohols without an external N ‐oxide co‐oxidant is described. The catalyst system is composed of a Cu/diamine complex inspired by the enzyme tyrosinase, along with dimethylaminopyridine (DMAP) or N ‐methylimidazole (NMI). The Cu catalyst system works without 2,2,6,6‐tetramethyl‐l‐piperidinoxyl (TEMPO) at ambient pressure and temperature, and displays activity for un‐activated secondary alcohols, which remain a challenging substrate for catalytic aerobic systems. Our work underscores the importance of finding alternative mechanistic pathways for alcohol oxidation, which complement Cu/TEMPO systems, and demonstrate, in this case, a preference for the oxidation of activated secondary over primary alcohols.

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