Catalytic role of nickel in the decarbonylative addition of phthalimides to alkynes

Albert Poater, Sai V. C. Vummaleti, Luigi Cavallo

Research output: Contribution to journalArticlepeer-review

19 Scopus citations

Abstract

Density functional theory calculations have been used to investigate the catalytic role of nickel(0) in the decarbonylative addition of phthalimides to alkynes. According to Kurahashi et al. the plausible reaction mechanism involves a nucleophilic attack of nickel at an imide group, giving a six-membered metallacycle, followed by a decarbonylation and insertion of an alkyne leading to a seven-membered metallacycle. Finally a reductive elimination process produces the desired product and regenerates the nickel(0) catalyst. In this paper, we present a full description of the complete reaction pathway along with possible alternative pathways, which are predicted to display higher upper barriers. Our computational results substantially confirm the proposed mechanism, offering a detailed geometrical and energetical understanding of all the elementary steps. © 2013 American Chemical Society.
Original languageEnglish (US)
Pages (from-to)6330-6336
Number of pages7
JournalOrganometallics
Volume32
Issue number21
DOIs
StatePublished - Oct 30 2013

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Inorganic Chemistry

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