Palladium- and nickel-catalyzed carbon-carbon bond insertion reactions with alkylidenesilacyclopropanes

Kay M. Buchner, K. A. Woerpel

Research output: Contribution to journalArticlepeer-review

Abstract

Palladium and nickel catalysts promoted highly selective carbon-carbon bond insertion reactions with di-tert-butyl-alkylidenesilacyclopropanes. Pd(PPh 3)4 was demonstrated to be the optimal catalyst, allowing for a variety of carbon-carbon π-bond insertion reactions. Depending on the nature of the carbon-carbon π bond, the insertion reaction proceeded with either direct insertion into the carbon(sp2)-silicon bond or allylic transposition. Ring-substituted alkylidenesilacyclopropanes required a nickel catalyst to afford insertion products. Using Ni(cod)2 as the carbon-carbon bond insertion catalyst, new double alkyne insertion products and alkene isomerization products were observed.

Original languageEnglish (US)
Pages (from-to)1661-1669
Number of pages9
JournalOrganometallics
Volume29
Issue number7
DOIs
StatePublished - Apr 12 2010

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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