Aminoalkylation of Indoles with [alpha]-Polyfluoroalkylated Cyclic Imines

The reaction of cyclic ketimines with indoles was studied. A dramatic difference between the electrophilicity of perfluoroalkyl-substituted and non-fluorinated imines was demonstrated. In good agreement with our calculations, the Friedel-Crafts-type alkylation of indoles only takes place with [alpha...

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Bibliographic Details
Published in:European journal of organic chemistry 2013-04, Vol.2013 (11), p.2237
Main Authors: Shevchenko, Nikolay E, Shmatova, Olga I, Balenkova, Elisabeth S, Roschenthaler, Gerd-Volker, Nenajdenko, Valentine G
Format: Article
Language:English
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Summary:The reaction of cyclic ketimines with indoles was studied. A dramatic difference between the electrophilicity of perfluoroalkyl-substituted and non-fluorinated imines was demonstrated. In good agreement with our calculations, the Friedel-Crafts-type alkylation of indoles only takes place with [alpha]-polyfluoroalkylated cyclic imines that are activated by boron trifluoride-diethyl ether. The reaction proceeds under mild conditions and provides the opportunity to obtain promising alkaloid-like structures that contain a fluoroalkyl group. As a result, [alpha]-CF3- and [alpha]-C2F5-substituted pyrrolidines, piperidines, and azepanes that contain an indole moiety can be prepared efficiently.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201201661