Premium
Quinone‐Catalyzed Selective Oxidation of Organic Molecules
Author(s) -
Wendlandt Alison E.,
Stahl Shan S.
Publication year - 2015
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201505017
Subject(s) - quinone , chemistry , electrophile , hydride , dehydrogenation , transamination , reagent , catalysis , redox , combinatorial chemistry , photochemistry , hydrogen atom abstraction , trifluoromethylation , amine gas treating , organic chemistry , radical , hydrogen , alkyl , trifluoromethyl , enzyme
Quinones are common stoichiometric reagents in organic chemistry. Para ‐ quinones with high reduction potentials, such as DDQ and chloranil, are widely used and typically promote hydride abstraction. In recent years, many catalytic applications of these methods have been achieved by using transition metals, electrochemistry, or O 2 to regenerate the oxidized quinone in situ. Complementary studies have led to the development of a different class of quinones that resemble the ortho‐quinone cofactors in copper amine oxidases and mediate the efficient and selective aerobic and/or electrochemical dehydrogenation of amines. The latter reactions typically proceed by electrophilic transamination and/or addition‐elimination reaction mechanisms, rather than hydride abstraction pathways. The collective observations show that the quinone structure has a significant influence on the reaction mechanism and has important implications for the development of new quinone reagents and quinone‐catalyzed transformations.