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

Kay M. Buchner, Keith Woerpel

Research output: Contribution to journalArticle

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

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Palladium
Nickel
palladium
insertion
Carbon
nickel
carbon
catalysts
Catalysts
products
Alkynes
Alkenes
alkynes
Silicon
Isomerization
isomerization
alkenes
rings
silicon

ASJC Scopus subject areas

  • Inorganic Chemistry
  • Organic Chemistry
  • Physical and Theoretical Chemistry

Cite this

Palladium- and nickel-catalyzed carbon-carbon bond insertion reactions with alkylidenesilacyclopropanes. / Buchner, Kay M.; Woerpel, Keith.

In: Organometallics, Vol. 29, No. 7, 12.04.2010, p. 1661-1669.

Research output: Contribution to journalArticle

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