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

78 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).
LanguageEnglish
Pages2971-2974
Number of pages4
JournalOrganic Letters
Volume5
Issue number16
DOIs
Publication statusPublished - 2003

Fingerprint

Oxides
preparation
oxides
Water
Poisons
Cyclization
Benzene
water
Hydrogen
Atoms
Temperature
initiators
hydrides
reagents
hydrogen atoms
benzene
tributyltin

Keywords

  • indolones
  • diethylphosphine oxide

Cite this

Murphy, J.A. ; Khan, T.A. ; Tripoli, R. ; Crawford, J.J. ; Martin, C.G. / Diethylphosphine oxide (DEPO): high-yielding and facile preparation of indolones in water. In: Organic Letters. 2003 ; Vol. 5, No. 16. pp. 2971-2974.
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Diethylphosphine oxide (DEPO): high-yielding and facile preparation of indolones in water. / Murphy, J.A.; Khan, T.A.; Tripoli, R.; Crawford, J.J.; Martin, C.G.

In: Organic Letters, Vol. 5, No. 16, 2003, p. 2971-2974.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Diethylphosphine oxide (DEPO): high-yielding and facile preparation of indolones in water

AU - Murphy, J.A.

AU - Khan, T.A.

AU - Tripoli, R.

AU - Crawford, J.J.

AU - Martin, C.G.

PY - 2003

Y1 - 2003

N2 - 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).

AB - 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).

KW - indolones

KW - diethylphosphine oxide

U2 - 10.1021/ol035173i

DO - 10.1021/ol035173i

M3 - Article

VL - 5

SP - 2971

EP - 2974

JO - Organic Letters

T2 - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 16

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