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 journalArticle

72 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 languageEnglish
Pages (from-to)2711-2714
Number of pages4
JournalOrganic Letters
Volume11
Issue number12
DOIs
Publication statusPublished - Jun 18 2009
Externally publishedYes

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Rhenium
Carbonyl compounds
carbonyl compounds
rhenium
aldehydes
Aldehydes
insertion
Allyl Compounds
Bearings (structural)
Molecules
Alkynes
Ethers
Alkenes
dienes
alkynes
Carbon Monoxide
alkenes
molecules
elimination
ethers

All Science Journal Classification (ASJC) codes

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

Cite this

Rhenium-catalyzed insertion of nonpolar and polar unsaturated molecules into an olefinic C-H bond. / Kuninobu, Yoichiro; Fujii, Yasuo; Matsuki, Takashi; Nishina, Yuta; Takai, Kazuhiko.

In: Organic Letters, Vol. 11, No. 12, 18.06.2009, p. 2711-2714.

Research output: Contribution to journalArticle

Kuninobu, Yoichiro ; Fujii, Yasuo ; Matsuki, Takashi ; Nishina, Yuta ; Takai, Kazuhiko. / Rhenium-catalyzed insertion of nonpolar and polar unsaturated molecules into an olefinic C-H bond. In: Organic Letters. 2009 ; Vol. 11, No. 12. pp. 2711-2714.
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