Regiospecific reductive elimination from diaryliodonium salts

Bijia Wang, Joseph W. Graskemper, Linlin Qin, Stephen G. DiMagno

Research output: Contribution to journalArticlepeer-review

75 Scopus citations

Abstract

(Figure Presented) 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 maingroup and transition metal ions. X=N3, OAc, PhO, CF3CH2O, SCN, PhS.

Original languageEnglish (US)
Pages (from-to)4079-4083
Number of pages5
JournalAngewandte Chemie - International Edition
Volume49
Issue number24
DOIs
StatePublished - Jun 1 2010

Keywords

  • Cyclophanes
  • Iodanes
  • Reductive elimination
  • Regiochemistry
  • Stereoelectronic effects

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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