Transition-Metal-Catalyzed Carbon-Carbon Bond Forming Reactions: Regio- and Chemoselective Iron(0)-Catalyzed Diene to Olefin Cross-Coupling Reactions

James M. Takacs, Lawrence G. Anderson, G. V. Bindu Madhavan, Mark W. Creswell, Franklin L. Seely, Wayne F. Devroy

Research output: Contribution to journalArticle

33 Citations (Scopus)

Abstract

The iron(0)-catalyzed cross coupling of certain allylic ethers to 2,3-disubstituted 1,3-butadienes results in either a formal [4 + 4] ene reaction across the diene or in the net 1,4-insertion of the diene unit into the C-H bond at the 2-position of the allylic ether. The course of the reaction is determined by the ligands attached to the iron(O) catalyst. The active catalyst can be generated in situ, and reactions proceed catalytic in iron(O) at or near ambient temperatures. These new coupling reactions generate synthetically useful functionality (stereodefined olefin and an allylic ether or a protected carbonyl) on either side of the newly formed carbon-carbon bond. The results of deuterium-labeling experiments suggest a catalytic cycle which involves initial oxidative coupling of the diene and allyl ether in the mechanism of these reactions.

Original languageEnglish (US)
Pages (from-to)2395-2398
Number of pages4
JournalOrganometallics
Volume5
Issue number11
DOIs
StatePublished - Jan 1 1986

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cross coupling
Alkenes
dienes
Ether
alkenes
Transition metals
Carbon
Iron
transition metals
ethers
iron
carbon
Catalysts
Ethers
Deuterium
Labeling
catalysts
Ligands
butadiene
marking

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

Cite this

Transition-Metal-Catalyzed Carbon-Carbon Bond Forming Reactions : Regio- and Chemoselective Iron(0)-Catalyzed Diene to Olefin Cross-Coupling Reactions. / Takacs, James M.; Anderson, Lawrence G.; Bindu Madhavan, G. V.; Creswell, Mark W.; Seely, Franklin L.; Devroy, Wayne F.

In: Organometallics, Vol. 5, No. 11, 01.01.1986, p. 2395-2398.

Research output: Contribution to journalArticle

Takacs, James M. ; Anderson, Lawrence G. ; Bindu Madhavan, G. V. ; Creswell, Mark W. ; Seely, Franklin L. ; Devroy, Wayne F. / Transition-Metal-Catalyzed Carbon-Carbon Bond Forming Reactions : Regio- and Chemoselective Iron(0)-Catalyzed Diene to Olefin Cross-Coupling Reactions. In: Organometallics. 1986 ; Vol. 5, No. 11. pp. 2395-2398.
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