Regiospecific Reductive Elimination from Diaryliodonium Salts


  • We thank the National Science Foundation (CHE 0717562) for support and the National Institutes of Health (RR016544-01) for infrastructure to conduct this research.


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Out-of-plane steric bulk furnished by a cyclophane substituent on iodine(III) strongly destabilizes the transition state in the reductive elimination from diaryliodonium salts and leads to regiochemical control (dubbed SECURE), as is demonstrated by computational and experimental studies. This approach should be general for high-valent main-group and transition metal ions. X=N3, OAc, PhO, CF3CH2O, SCN, PhS.