Palladium catalyzed tandem alkenyl- and aryl-C–N bond formation: a cascade N-annulation route to 4-, 5-, 6- and 7-chloroindoles

A series of trihalogenated alkenylbenzenes undergo consecutive palladium catalyzed inter- and intramolecular amination reactions to deliver a series of 1-functionalized mono-chloroindoles. 4-, 5-, 6- and 7-Chloroindoles can all be prepared; carbamates, anilines and amines can be employed as the N-nu...

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Published inTetrahedron Vol. 66; no. 33; pp. 6632 - 6638
Main Authors Henderson, Luke C., Lindon, Matthew J., Willis, Michael C.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 14.08.2010
Elsevier
Subjects
Online AccessGet full text
ISSN0040-4020
1464-5416
DOI10.1016/j.tet.2010.05.046

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Abstract A series of trihalogenated alkenylbenzenes undergo consecutive palladium catalyzed inter- and intramolecular amination reactions to deliver a series of 1-functionalized mono-chloroindoles. 4-, 5-, 6- and 7-Chloroindoles can all be prepared; carbamates, anilines and amines can be employed as the N-nucleophile. [Display omitted]
AbstractList A series of trihalogenated alkenylbenzenes undergo consecutive palladium catalyzed inter- and intramolecular amination reactions to deliver a series of 1-functionalized mono-chloroindoles. 4-, 5-, 6- and 7-Chloroindoles can all be prepared; carbamates, anilines and amines can be employed as the N-nucleophile. [Display omitted]
A series of trihalogenated alkenylbenzenes undergo consecutive palladium catalyzed inter- and intramolecular amination reactions to deliver a series of 1-functionalized mono-chloroindoles. 4-, 5-, 6- and 7-Chloroindoles can all be prepared: carbamates, anilines and amines can be employed as the N-nucleophile. (C) 2010 Elsevier Ltd. All rights reserved.
Author Willis, Michael C.
Lindon, Matthew J.
Henderson, Luke C.
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Issue 33
Keywords Amination
Indole
Palladium
FUNCTIONALIZATION
OXYGEN
DIRECT ARYLATION
HETEROCYCLES
COUPLING REACTIONS
HALOGENATED NITROGEN
INDOLES
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Snippet A series of trihalogenated alkenylbenzenes undergo consecutive palladium catalyzed inter- and intramolecular amination reactions to deliver a series of...
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SubjectTerms Amination
Chemistry
Chemistry, Organic
Indole
Palladium
Physical Sciences
Science & Technology
Title Palladium catalyzed tandem alkenyl- and aryl-C–N bond formation: a cascade N-annulation route to 4-, 5-, 6- and 7-chloroindoles
URI https://dx.doi.org/10.1016/j.tet.2010.05.046
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