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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Bibliographic Details
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
Amination
Chemistry
Chemistry, Organic
Indole
Palladium
Physical Sciences
Science & Technology
Amination
Indole
Palladium
FUNCTIONALIZATION
OXYGEN
DIRECT ARYLATION
HETEROCYCLES
COUPLING REACTIONS
HALOGENATED NITROGEN
INDOLES
Online AccessGet full text
ISSN0040-4020
1464-5416
DOI10.1016/j.tet.2010.05.046

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Summary: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]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2010.05.046