Development of Radical Reactions with Zirconocene Complexes as Electron Transfer Reagents

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  • Kazuya Fujita
    Department of Material Chemistry, Graduate School of Engineering, Kyoto University
  • Hideki Yorimitsu
    Department of Material Chemistry, Graduate School of Engineering, Kyoto University
  • Koichiro Oshima
    Department of Material Chemistry, Graduate School of Engineering, Kyoto University

Abstract

<jats:title>Abstract</jats:title> <jats:p>Bis(cyclopentadienyl)zirconium chloride hydride (Schwartz reagent) proved to be an efficient radical chain carrier for radical reduction of organic halides. Treatment of 1-bromoadamantane with Cp2Zr(H)Cl in THF at 25 °C in the presence of triethylborane furnished adamantane quantitatively. Radical cyclization of 2-haloalkyl allyl ethers afforded five-membered products under the same reaction conditions. Reduction with Cp2Zr(H)Cl generated in situ from Cp2ZrCl2 and sodium bis(2-methoxyethoxy)aluminium hydride (Red-Al) also proceeded smoothly. Moreover, the reduction could function by using a catalytic amount of Cp2ZrCl2. A zirconocene–olefin complex also induced reductive radical cyclization of 2-haloalkyl allyl ethers in THF. This complex served as a single electron transfer reagent to promote the radical cyclization. Furthermore, the cyclization reaction in DME afforded 3-tetrahydrofuranylmethylzirconium efficiently.</jats:p>

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