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Copper‐Catalyzed Aerobic Dehydrogenation of C–C to C=C Bonds in the Synthesis of Pyridazinones
Author(s) -
Liang Lei,
Yang Guanyu,
Xu Fengrong,
Niu Yan,
Sun Qi,
Xu Ping
Publication year - 2013
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.201300640
Subject(s) - dehydrogenation , chemistry , catalysis , alkoxy group , copper , medicinal chemistry , selectivity , oxygen , organic chemistry , combinatorial chemistry , alkyl
A simple and efficient procedure for the synthesis of pyridazin‐3(2 H )‐ones through copper‐catalyzed dehydrogenation of a single C–C bond of 4,5‐dihydropyridazin‐3(2 H )‐ones to a C=C bond with oxygen as the terminal oxidant is described. Functional groups including hydroxy, carboxylic, bromo, chloro, cyano, nitro and alkoxy were all tolerated under the reaction conditions. Moreover, this methodology was applied to the preparation of a series of structurally similar N‐substituted 6‐phenylpyridazinone compounds containing fluorine. The dehydrogenation reactions exhibit good yields and selectivity.