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MnO 2 /TBHP: A Versatile and User‐Friendly Combination of Reagents for the Oxidation of Allylic and Benzylic Methylene Functional Groups
Author(s) -
Serra Stefano
Publication year - 2015
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.201500829
Subject(s) - chemistry , allylic rearrangement , chemoselectivity , methylene , regioselectivity , reagent , decomposition , substrate (aquarium) , medicinal chemistry , combinatorial chemistry , functional group , catalysis , organic chemistry , oceanography , polymer , geology
In the presence of activated MnO 2 , tert ‐butyl hydroperoxide (TBHP) in CH 2 Cl 2 is able to oxidize the allylic and benzylic methylene groups of different classes of compounds. I describe a one‐pot oxidation protocol based on two sequential steps. In the first step, carried out at low temperature, MnO 2 catalyses the oxidation of the methylene group. This is followed by a second step where reaction temperature is increased, allowing MnO 2 both to catalyse the decomposition of unreacted TBHP and to oxidize allylic alcohols that could possibly be formed. The proposed oxidation procedure is generally applicable, although its efficiency, regioselectivity, and chemoselectivity are strongly dependent on the structure of the substrate.