Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 133, Issue 20, Pages 7672-7675Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja2017202
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Funding
- MEXT [22000008]
- Global COE Program for Chemistry Innovation
- Grants-in-Aid for Scientific Research [22000008, 11J08207, 23750100] Funding Source: KAKEN
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The 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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