Mechanistic complexity in organo-SOMO activation

James J. Devery, Jay C. Conrad, David W.C. MacMillan, Robert A. Flowers

Research output: Contribution to journalArticle

63 Scopus citations

Abstract

Wet chemistry: Organo-SOMO activation is an intricate process. The catalyst is deactivated in the absence of H2O and its concentration is maintained with 2 equivalents of H2O. The kinetic role of ceric ammonium nitrate (CAN) is masked by phase transfer and its limited solubility is enhanced by added H2O. Mechanistic studies show that careful addition of H2O to dried reagents greatly enhances reaction. TMS=trimethylsilyl.

Original languageEnglish (US)
Pages (from-to)6106-6110
Number of pages5
JournalAngewandte Chemie - International Edition
Volume49
Issue number35
DOIs
StatePublished - Aug 16 2010

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

Keywords

  • Ceric ammonium nitrate
  • Organocatalysis
  • Phase transfer
  • Reaction mechanisms
  • Single electron transfer

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