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Mechanistic Insight into the Palladium‐Catalyzed 1,4‐Oxidation of 1,3‐Dienes to 1,4‐Dicarboxy‐alk‐2‐enes
Author(s) -
Eastgate Martin D.,
Buono Frederic G.
Publication year - 2009
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.200901614
Subject(s) - palladium , adduct , chemistry , catalysis , diene , bicyclic molecule , combinatorial chemistry , organic chemistry , medicinal chemistry , photochemistry , natural rubber
Side products get involved: The 1,4‐oxidation of a diene transforms a simple hydrocarbon into an extremely useful intermediate. A complex formed in situ between palladium and a bicyclic Diels–Alder adduct, which is produced as a side product during the reaction, was responsible for the high rate and high diastereoselectivity observed in the oxidation of cyclohexadiene (see scheme).