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Rhenium-Catalyzed Insertion of Nonpolar and Polar Unsaturated Molecules into an Olefinic C−H Bond

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journal contribution
posted on 18.06.2009, 00:00 by Yoichiro Kuninobu, Yasuo Fujii, Takashi Matsuki, Yuta Nishina, Kazuhiko Takai
Treatment of olefins bearing a directing group with α,β-unsaturated carbonyl compounds, alkynes, or aldehydes in the presence of a catalytic amount of a rhenium complex, [ReBr(CO)3(thf)]2 gave γ,δ-unsaturated carbonyl compounds, dienes, and allyl silyl ethers, respectively. This reaction proceeds via C−H bond activation, insertion of unsaturated molecules into the formed rhenium−carbon bond, and then reductive elimination (or transmetalation in the case of aldehydes).