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Base-Stabilized Nitrilium Ions as Convenient Imine Synthons

Author:
van Dijk, Tom, Bakker, Martijn S., Holtrop, Flip, Nieger, Martin, Slootweg, J. Chris, Lammertsma, Koop
Source:
Organic letters 2015 v.17 no.6 pp. 1461-1464
ISSN:
1523-7052
Subject:
Lewis bases, amidines, chemical reactions, chemical structure, imines, ions, pyridines
Abstract:
A simple and efficient methodology is presented for the synthesis of a wide range of substituted imines. It is based on stabilizing readily available, but thermally labile, N-alkylnitrilium triflates with pyridine or DMAP to moderately air-stable adducts. These base-stabilized imine synthons react conveniently with phosphorus- and nitrogen-based nucleophiles to amidines and phosphaamidines.
Agid:
5790356