(Porphinato)iron-Catalyzed Addition Reactions of Thiols to Alkenes via (σ-Alkyl)iron(II) Complexes

Masayuki Takeuchi, Hisashi Shimakoshi, Koji Kano

Research output: Contribution to journalArticlepeer-review

17 Citations (Scopus)

Abstract

The Markovnikov-type addition of thiols (derived from the corresponding disulfides) to alkenes occurs in anaerobic benzene-ethanol solutions containing NaBH 4 and (porphinato)iron(III) chloride (Por-FeIIICl). For example, the reaction of styrene with diphenyl disulfide affords phenyl 1-phenylethyl sulfide. It has been assumed that the hydride transfer from BH4- to styrene yields 1-phenylethanide which is stabilized by coordinating to Por-FeII and that the resulting (σ-alkyl)iron(II) complex having a carbanion character reacts with diphenyl disulfide to give phenyl 1-phenylethyl sulfide and the thiophenolate ion.

Original languageEnglish
Pages (from-to)1208-1213
Number of pages6
JournalOrganometallics
Volume13
Issue number4
DOIs
Publication statusPublished - Apr 1 1994
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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