Phenyl vs. Ferrocenyl Cyclometallation Selectivity: Diastereoselective Synthesis of an Enantiopure Iridacycle

Ross A. Arthurs, Peter N. Horton, Simon J. Coles, Christopher J. Richards

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Abstract

Ferrocenyl (Fc) and phenyl (Ph) containing imines FcCH=NCH(R)Ph and FcCH(R)N=CHPh (R = H and Me) were cycloiridated using [Cp*IrCl2]2 with NaOAc in CH2Cl2. All resulted in the formation of neutral chloride ligated half-sandwich iridacycles as a result of ortho-phenyl and not alpha-ferrocenyl C–H activation. The complexes derived from FcCH=NCH(R)Ph (R = H, Me) were obtained as a mixture of E and Z imine isomers, and with R = Me the product obtained from the (S)-imine was isolated by recrystallisation as a single diastereoisomer. The configuration was determined by an X-ray crystal structure analysis as SC,RIr,E.
Original languageEnglish
Pages (from-to)229–232
JournalEuropean Journal of Inorganic Chemistry
Volume2017
Issue number2
Early online date30 Aug 2016
DOIs
Publication statusPublished - 10 Jan 2017

Keywords

  • Metallacycles
  • Iridium
  • Iron
  • Sandwich complexes
  • Regioselectivity
  • Diastereoselectivity
  • Chirality

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