Premium
ortho ‐Olefination of Arylaldehyde O ‐Methyloximes through Palladium‐Catalyzed C–H Activation
Author(s) -
Xu Zhipeng,
Xiang Biao,
Sun Peipei
Publication year - 2012
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.201200393
Subject(s) - chemistry , catalysis , palladium , hydrolysis , kinetic isotope effect , solvent , medicinal chemistry , reaction mechanism , kinetic energy , organic chemistry , deuterium , physics , quantum mechanics
Palladium(II)‐catalyzed ortho ‐olefination of arylaldehyde O ‐methyloximes by using O ‐methyloxime as a directing group gave 2‐alkenylarylaldehyde O ‐methyloximes in moderate to good yields. After various reaction parameters (catalyst, oxidant, solvent, and reaction temperature) were examined, the optimal conditions for the reaction were identified. 2‐Alkenylarylaldehydes could be obtained conveniently by hydrolysis of the coupling products. The kinetic isotope effect ( k H / k D ) for the C–H bond activation was provided, and the possible mechanism of the reaction was proposed.