Iron-Catalyzed Stereospecific Activation of Olefinic C–H Bonds with Grignard Reagent for Synthesis of Substituted Olefins
2011; American Chemical Society; Volume: 133; Issue: 20 Linguagem: Inglês
10.1021/ja2017202
ISSN1943-2984
AutoresLaurean Ilies, Sobi Asako, Eiichi Nakamura,
Tópico(s)Asymmetric Hydrogenation and Catalysis
ResumoThe reaction of an aryl Grignard reagent with a cyclic or acyclic olefin possessing a directing group such as pyridine or imine results in the stereospecific substitution of the olefinic C-H bond syn to the directing group. The reaction takes place smoothly and without isomerization of the product olefin in the presence of a mild oxidant (1,2-dichloro-2-methylpropane) and an aromatic cosolvent. Several lines of evidence suggest that the reaction proceeds via iron-catalyzed olefinic C-H bond activation rather than an oxidative Mizoroki-Heck-type reaction.
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