Rhenium-catalyzed insertion of nonpolar and polar unsaturated molecules into an olefinic C-H bond

Yoichiro Kuninobu; Yasuo Fujii; Takashi Matsuki; Yuta Nishina; Kazuhiko Takai

doi:10.1021/ol900962v

Rhenium-catalyzed insertion of nonpolar and polar unsaturated molecules into an olefinic C-H bond

Yoichiro Kuninobu, Yasuo Fujii, Takashi Matsuki, Yuta Nishina, Kazuhiko Takai

Research output: Contribution to journal › Article › peer-review

84 Citations (Scopus)

Abstract

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).

Original language	English
Pages (from-to)	2711-2714
Number of pages	4
Journal	Organic letters
Volume	11
Issue number	12
DOIs	https://doi.org/10.1021/ol900962v
Publication status	Published - Jun 18 2009
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol900962v

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abstract = "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).",

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T1 - Rhenium-catalyzed insertion of nonpolar and polar unsaturated molecules into an olefinic C-H bond

AU - Kuninobu, Yoichiro

AU - Fujii, Yasuo

AU - Matsuki, Takashi

AU - Nishina, Yuta

AU - Takai, Kazuhiko

PY - 2009/6/18

Y1 - 2009/6/18

N2 - 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).

AB - 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).

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JO - Organic letters

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Rhenium-catalyzed insertion of nonpolar and polar unsaturated molecules into an olefinic C-H bond

Abstract

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