Palladium-catalyzed homogeneous coupling reactions of steroids with organostannanes

Rita Skoda-Földes, Zita Csákai, Lászlo Kollár, Judit Horváth, Zoltán Tuba

Research output: Contribution to journalArticle

21 Citations (Scopus)

Abstract

Direct and carbonylative coupling reactions of various steroid derivatives possessing iodo- and bromo-alkenyl moiety (17-iodo-androst-16-ene, 1, 17-bromoandrost-2,16-diene. 2, 17-iodo-4-aza-4-methylandrost-16-en-3-one, 3, 17-iodo-4-azaandrost-16-en-3-one, 4) with vinyltributylstannane and ethynyltributylstannane were carried out in the presence of various palladium catalysts. While carbonylation took place only with vinyltributylstannane, 17-vinyl-, and 17-ethynyl-Δ16 steroids were produced via direct coupling with vinyltributylstannane and ethynyltributylstannane, respectively. Activities of some catalysts based on Pd(0) and Pd(II) precursors were compared, and Pd(PPh3)4 was found to be superior to other complexes in most cases. In the coupling of 17-iodoandrost-16-ene with organostannanes Pd2(dba)3 + 8 AsPh3 in situ catalyst was found to be even more effective.

Original languageEnglish
Pages (from-to)812-816
Number of pages5
JournalSteroids
Volume60
Issue number12
DOIs
Publication statusPublished - Dec 1995

Keywords

  • 17-iodoandrost-16-ene derivatives
  • carbonylative vinylation
  • homogeneous coupling reaction
  • palladium-phosphine catalysts
  • vinylation

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Endocrinology
  • Pharmacology
  • Clinical Biochemistry
  • Organic Chemistry

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