An Interrupted Schmidt Reaction: C–C Bond Formation Arising from Nitrilium Ion Capture

The rerouting of the nitrilium ion formed in the Schmidt reaction of ketones and TMSN3 to encompass C–C bond formation with an electron-rich aromatic group is reported. Thus, when the reaction is carried out in HFIP using AlCl3 or AlBr3 as the promoter, imines, iminium ions, or enamide derivatives a...

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Bibliographic Details
Published in:Organic letters 2018-10, Vol.20 (20), p.6354-6358
Main Authors: Charaschanya, Manwika, Li, Kelin, Motiwala, Hashim F, Aubé, Jeffrey
Format: Article
Language:English
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Summary:The rerouting of the nitrilium ion formed in the Schmidt reaction of ketones and TMSN3 to encompass C–C bond formation with an electron-rich aromatic group is reported. Thus, when the reaction is carried out in HFIP using AlCl3 or AlBr3 as the promoter, imines, iminium ions, or enamide derivatives are obtained through one-pot procedures. The scope and possible mechanisms of these new transformations are considered.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.8b02531