Regioselective Preferential Nucleophilic Addition of N-Heterocycles onto Haloarylalkynes over N-Arylation of Aryl Halides

The study of preferential addition of heterocyclic amines onto halo-substituted arylalkynes over N-arylation under various catalytic conditions is described. The present work supports and confirms the mechanistic pathway of our recent work on the tandem synthesis of indolo- and pyrrolo-[2,1-a]isoqui...

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Bibliographic Details
Published in:Organic letters 2012-02, Vol.14 (4), p.1106-1109
Main Authors: Joshi, Megha, Tiwari, Rakesh, Verma, Akhilesh Kumar
Format: Article
Language:English
Subjects:
Alkynes - chemistry
Halogens - chemistry
Macrocyclic Compounds - chemistry
Models, Molecular
Molecular Structure
Oxidation-Reduction
Stereoisomerism
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Summary:The study of preferential addition of heterocyclic amines onto halo-substituted arylalkynes over N-arylation under various catalytic conditions is described. The present work supports and confirms the mechanistic pathway of our recent work on the tandem synthesis of indolo- and pyrrolo-[2,1-a]isoquinolines via hydroamination followed by oxidative addition and not vice versa.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol203491p