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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

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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).