Inter- and intramolecular palladium-catalyzed hydrocarbonation of methylenecyclopropanes with carbon pronucleophiles

Naofumi Tsukada, Akinori Shibuya, Itaru Nakamura, Haruo Kitahara, Yoshinori Yamamoto

Research output: Contribution to journalArticle

26 Citations (Scopus)

Abstract

The inter- and intramolecular additions of pronucleophiles to methylenecyclopropanes proceeded smoothly in the presence of catalytic amounts of Pd(PPh3)4, affording hydrocarbonation products in good to high yields. The ring opening of methylenecyclopropanes mainly occurred at the distal position to the exomethylene. In some cases, proximal bond cleavage also took place. The mode of ring opening depended upon both the structure of the pronucleophile and the substituent at the exomethylene carbon.

Original languageEnglish
Pages (from-to)8833-8844
Number of pages12
JournalTetrahedron
Volume55
Issue number29
DOIs
Publication statusPublished - 1999 Jul 16

Keywords

  • Hydrocarbonation
  • Methylenecyclopropane
  • Palladium catalyzed reaction
  • Pronucleophile

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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