Premium
Ruthenium‐Catalyzed Oxidant‐Free Allylation of Aromatic Ketoximes with Allylic Acetates at Room Temperature
Author(s) -
Manikandan Rajendran,
Madasamy Padmaja,
Jeganmohan Masilamani
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201502284
Subject(s) - chemistry , allylic rearrangement , regioselectivity , catalysis , dichloroethane , organic chemistry , medicinal chemistry , ruthenium , base (topology) , tert butyl hydroperoxide , mathematical analysis , mathematics
Substituted aromatic ketoximes reacted efficiently with allylic acetates in the presence of {[RuCl 2 ( p ‐cymene)] 2 } and AgSbF 6 in 1,2‐dichloroethane at ambient temperature, providing ortho ‐allyl aromatic ketoximes in a highly regioselective manner without an oxidant. In the reaction, the acetate group of allyl acetate acts as a base to activate the CH bond of aromatics. Later, ortho ‐allyl aromatic ketoximes were converted into ortho ‐allyl aromatic ketones in the presence of HCl.