The rerouting of the nitrilium ion formed in the Schmidt reaction of ketones and TMSN to encompass C-C bond formation with an electron-rich aromatic group is reported. Thus, when the reaction is carried out in HFIP using AlCl or AlBr 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.
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| http://dx.doi.org/10.1021/acs.orglett.8b02531 | DOI Listing |
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