Preparation of 3-alkyl-oxindoles by copper(II)-mediated C-H, Ar-H coupling followed by decarboxyalkylation

David S. Pugh; Johannes E.M.N. Klein; Alexis Perry; Richard J.K. Taylor

doi:10.1055/s-0029-1219392

Preparation of 3-alkyl-oxindoles by copper(II)-mediated C-H, Ar-H coupling followed by decarboxyalkylation

David S. Pugh, Johannes E.M.N. Klein, Alexis Perry, Richard J.K. Taylor

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

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Abstract

A novel route for the conversion of anilides into 3-alkyl-oxindoles is described in which a copper(II)-mediated cyclization process is followed by an acid-mediated decarboxyalkylation. Scope and limitation studies are reported together with a telescoped variant which incorporates in situ N-deprotection.

Original language	English (US)
Pages (from-to)	934-938
Number of pages	5
Journal	Synlett
Issue number	6
DOIs	https://doi.org/10.1055/s-0029-1219392
State	Published - 2010
Externally published	Yes

Keywords

3-alkyl-oxindoles
Anilides
C-H activation
Copper(II) catalysis
Cyclisation
Decarboxyalkylation
Oxindoles

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10.1055/s-0029-1219392

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abstract = "A novel route for the conversion of anilides into 3-alkyl-oxindoles is described in which a copper(II)-mediated cyclization process is followed by an acid-mediated decarboxyalkylation. Scope and limitation studies are reported together with a telescoped variant which incorporates in situ N-deprotection.",

keywords = "3-alkyl-oxindoles, Anilides, C-H activation, Copper(II) catalysis, Cyclisation, Decarboxyalkylation, Oxindoles",

author = "Pugh, {David S.} and Klein, {Johannes E.M.N.} and Alexis Perry and Taylor, {Richard J.K.}",

year = "2010",

doi = "10.1055/s-0029-1219392",

language = "English (US)",

pages = "934--938",

journal = "Synlett",

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AU - Pugh, David S.

AU - Klein, Johannes E.M.N.

AU - Perry, Alexis

AU - Taylor, Richard J.K.

PY - 2010

Y1 - 2010

N2 - A novel route for the conversion of anilides into 3-alkyl-oxindoles is described in which a copper(II)-mediated cyclization process is followed by an acid-mediated decarboxyalkylation. Scope and limitation studies are reported together with a telescoped variant which incorporates in situ N-deprotection.

AB - A novel route for the conversion of anilides into 3-alkyl-oxindoles is described in which a copper(II)-mediated cyclization process is followed by an acid-mediated decarboxyalkylation. Scope and limitation studies are reported together with a telescoped variant which incorporates in situ N-deprotection.

KW - 3-alkyl-oxindoles

KW - Anilides

KW - C-H activation

KW - Copper(II) catalysis

KW - Cyclisation

KW - Decarboxyalkylation

KW - Oxindoles

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DO - 10.1055/s-0029-1219392

M3 - Article

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SP - 934

EP - 938

JO - Synlett

JF - Synlett

IS - 6

ER -

Preparation of 3-alkyl-oxindoles by copper(II)-mediated C-H, Ar-H coupling followed by decarboxyalkylation

Abstract

Keywords

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