Rh2(II)-Catalyzed Selective Aminomethylene Migration from Styryl Azides

Rh2(II)-Carboxylate complexes were discovered to promote the selective migration of aminomethylenes in β,β-disubstituted styryl azides to form 2,3-disubstituted indoles. Mechanistic data are also presented that suggest that the migration occurs stepwise before diffusion of the iminium ion.

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Bibliographic Details
Published in:Organic letters 2013-02, Vol.15 (4), p.824-827
Main Authors: Kong, Chen, Jana, Navendu, Driver, Tom G
Format: Article
Language:English
Subjects:
Azides - chemistry
Carboxylic Acids - chemistry
Catalysis
Cyclization
Imines - chemistry
Indoles - chemical synthesis
Indoles - chemistry
Molecular Structure
Organometallic Compounds - chemistry
Rhodium - chemistry
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Description
Summary:Rh2(II)-Carboxylate complexes were discovered to promote the selective migration of aminomethylenes in β,β-disubstituted styryl azides to form 2,3-disubstituted indoles. Mechanistic data are also presented that suggest that the migration occurs stepwise before diffusion of the iminium ion.
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/ol400137q