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

Murphy, J.A. and Khan, T.A. and Tripoli, R. and Crawford, J.J. and Martin, C.G. (2003) Diethylphosphine oxide (DEPO): high-yielding and facile preparation of indolones in water. Organic Letters, 5 (16). pp. 2971-2974. ISSN 1523-7060 (https://doi.org/10.1021/ol035173i)

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).

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• Item metadata

  Item type:	Article
  ID code:	38514
  Dates:	Date Event 2003 Published
  Subjects:	Science > Chemistry
  Department:	Faculty of Science > Pure and Applied Chemistry
  Depositing user:	Pure Administrator
  Date deposited:	14 Mar 2012 16:04
  Last modified:	22 May 2025 04:19
  URI:	https://strathprints.strath.ac.uk/id/eprint/38514