Homogeneous coupling and carbonylation reactions of steroids possessing iodoalkene moieties. Catalytic and mechanistic aspects

Rita Skoda-Földes, Judit Horváth, Zoltán Tuba, László Kollár

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

Both 17-iodo-16-ene and 6-iodo-5-ene functionalities of androstane derivatives (17-iodo-4-aza-5α-androsta-16-en-3-one (1), 6-iodo-17-methoxycarbonyl-4-aza-androsta-5,16-dien-3-one (2), 6,17-diiodo-4-aza-androsta-5,16-dien-3-one (3), 17-iodo-androsta-16-ene (4), 6-iodo-17-(N,N-pentamethylene-carboxamido)-4-aza-androst-5,16-dien-3-one (5)) react with vinyl-tributyltin in a Stille reaction. However, palladium-catalysed carbonylation takes place selectively in position 17. The oxidative addition of 'iodo-vinyl' functionalities to in situ formed Pd(0)-triphenylphosphine species was observed by 31P-NMR spectroscopy. Dinuclear palladium(II) steroidal alkenyl or acyl species were detected under argon or carbon monoxide, respectively, when the 6-iodo-5-ene functionality (in ring B) was attached to a lactam moiety (ring A) in the steroidal substrate. In addition to monomeric species some oligomeric ones were also formed depending on the reaction conditions (gas atmosphere, solvent).

Original languageEnglish
Pages (from-to)94-100
Number of pages7
JournalJournal of Organometallic Chemistry
Volume586
Issue number1
DOIs
Publication statusPublished - Jul 31 1999

Keywords

  • Iodo-alkene
  • Oxidative addition
  • Palladium
  • Phosphine
  • Steroids

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry
  • Materials Chemistry

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