Diethylphosphine oxide (DEPO): high-yielding and facile preparation of indolones in water

J.A. Murphy, T.A. Khan, R. Tripoli, J.J. Crawford, C.G. Martin

Research output: Contribution to journalArticle

79 Citations (Scopus)

Abstract

Indolones are prepared in excellent yield at 80 °C in water by radical reaction (aryl radical formation, hydrogen atom abstraction, cyclization, and rearomatization) mediated by the reagent diethylphosphine oxide (DEPO). The reaction features V-501 as a water-soluble initiator; no other additives are needed. The process proceeds at a much lower temperature than is required for efficient reaction with toxic tributyltin hydride in benzene and permits significantly higher isolated yields than the corresponding reaction mediated by ethylpiperidine hypophosphite (EPHP).
Original languageEnglish
Pages (from-to)2971-2974
Number of pages4
JournalOrganic Letters
Volume5
Issue number16
DOIs
Publication statusPublished - 2003

Keywords

  • indolones
  • diethylphosphine oxide

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