Copper-catalysed approach to spirocyclic oxindoles via a direct C-H, Ar-H functionalisation

Catherine L. Moody; Vilius Franckevičius; Pauline Drouhin; Johannes E.M.N. Klein; Richard J.K. Taylor

doi:10.1016/j.tetlet.2012.01.120

Copper-catalysed approach to spirocyclic oxindoles via a direct C-H, Ar-H functionalisation

Catherine L. Moody, Vilius Franckevičius, Pauline Drouhin, Johannes E.M.N. Klein, Richard J.K. Taylor

Chemistry (Twin Cities)

Research output: Contribution to journal › Article › peer-review

50 Scopus citations

Abstract

A practical and efficient entry to spirocyclic oxindoles from readily accessible anilide precursors, using only catalytic amounts of an inexpensive copper salt together with air as the sole re-oxidant, is described. In addition to providing access to a broad range of spiro-oxindole products, the utility of this method is demonstrated in a formal synthesis of the natural product, horsfiline.

Original language	English (US)
Pages (from-to)	1897-1899
Number of pages	3
Journal	Tetrahedron Letters
Volume	53
Issue number	15
DOIs	https://doi.org/10.1016/j.tetlet.2012.01.120
State	Published - Apr 11 2012

Bibliographical note

Funding Information:
We gratefully acknowledge the University of York (C.L.M., V.F., P.D., J.E.M.N.K.) and the University of York Wild Fund (P.D., J.E.M.N.K.) for generous financial support, as well as Dr. Robert Thatcher and Dr. Adrian Whitwood for help with X-ray crystallographic analysis.

Keywords

C-H activation
Copper catalysis
Natural product synthesis
Radical cyclisation
Spirocyclic oxindoles

Publisher link

10.1016/j.tetlet.2012.01.120

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abstract = "A practical and efficient entry to spirocyclic oxindoles from readily accessible anilide precursors, using only catalytic amounts of an inexpensive copper salt together with air as the sole re-oxidant, is described. In addition to providing access to a broad range of spiro-oxindole products, the utility of this method is demonstrated in a formal synthesis of the natural product, horsfiline.",

keywords = "C-H activation, Copper catalysis, Natural product synthesis, Radical cyclisation, Spirocyclic oxindoles",

author = "Moody, {Catherine L.} and Vilius Franckevi{\v c}ius and Pauline Drouhin and Klein, {Johannes E.M.N.} and Taylor, {Richard J.K.}",

note = "Funding Information: We gratefully acknowledge the University of York (C.L.M., V.F., P.D., J.E.M.N.K.) and the University of York Wild Fund (P.D., J.E.M.N.K.) for generous financial support, as well as Dr. Robert Thatcher and Dr. Adrian Whitwood for help with X-ray crystallographic analysis. ",

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AU - Moody, Catherine L.

AU - Franckevičius, Vilius

AU - Drouhin, Pauline

AU - Klein, Johannes E.M.N.

AU - Taylor, Richard J.K.

N1 - Funding Information: We gratefully acknowledge the University of York (C.L.M., V.F., P.D., J.E.M.N.K.) and the University of York Wild Fund (P.D., J.E.M.N.K.) for generous financial support, as well as Dr. Robert Thatcher and Dr. Adrian Whitwood for help with X-ray crystallographic analysis.

PY - 2012/4/11

Y1 - 2012/4/11

N2 - A practical and efficient entry to spirocyclic oxindoles from readily accessible anilide precursors, using only catalytic amounts of an inexpensive copper salt together with air as the sole re-oxidant, is described. In addition to providing access to a broad range of spiro-oxindole products, the utility of this method is demonstrated in a formal synthesis of the natural product, horsfiline.

AB - A practical and efficient entry to spirocyclic oxindoles from readily accessible anilide precursors, using only catalytic amounts of an inexpensive copper salt together with air as the sole re-oxidant, is described. In addition to providing access to a broad range of spiro-oxindole products, the utility of this method is demonstrated in a formal synthesis of the natural product, horsfiline.

KW - C-H activation

KW - Copper catalysis

KW - Natural product synthesis

KW - Radical cyclisation

KW - Spirocyclic oxindoles

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Copper-catalysed approach to spirocyclic oxindoles via a direct C-H, Ar-H functionalisation

Abstract

Bibliographical note

Keywords

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