Premium
DoE (Design of Experiments) Assisted Allylic Hydroxylation of Enones Catalysed by a Copper–Aluminium Mixed Oxide
Author(s) -
GarcíaCabeza Ana Leticia,
MarínBarrios Rubén,
Azarken Redouan,
MorenoDorado F. Javier,
Ortega María J.,
Vidal Hilario,
Gatica José M.,
Massanet Guillermo M.,
Guerra Francisco M.
Publication year - 2013
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.201301145
Subject(s) - chemistry , allylic rearrangement , hydroxylation , catalysis , reagent , substrate (aquarium) , copper , oxide , copper oxide , organic chemistry , combinatorial chemistry , oceanography , enzyme , geology
The allylic hydroxylation of enones using dioxygen as the oxidant has been studied. The reaction was first examined in the absence of any catalyst, using β‐ionone as a model substrate. Then a new copper–aluminium mixed oxide, Cu–Al Ox, was prepared and characterized in order to be used as a catalyst. This oxide showed good activity, and provided the corresponding γ‐ or ϵ‐hydroxylated enones, starting from different α,β‐ or α,β,γ,δ‐unsaturated ketones. In all cases, the yields were significantly improved compared to experiments run in the absence of the catalyst. The reaction was selective, and the formation of epoxides or other overoxidation products was detected only to a minor extent. The described procedure is a technically straightforward synthetic alternative to those methods described to date involving many reaction steps or toxic reagents. The reactions were optimized using design of experiments techniques (DoE).