(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 journalArticle

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

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Addition reactions
Styrene
Alkenes
disulfides
Sulfides
Sulfhydryl Compounds
thiols
alkenes
Iron
styrenes
iron
sulfides
Benzene
Hydrides
Disulfides
Chlorides
Ethanol
Ions
hydrides
ethyl alcohol

All Science Journal Classification (ASJC) codes

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

Cite this

(Porphinato)iron-Catalyzed Addition Reactions of Thiols to Alkenes via (σ-Alkyl)iron(II) Complexes. / Takeuchi, Masayuki; Shimakoshi, Hisashi; Kano, Koji.

In: Organometallics, Vol. 13, No. 4, 01.04.1994, p. 1208-1213.

Research output: Contribution to journalArticle

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