4.8 Article

Base-Stabilized Nitrilium Ions as Convenient Imine Synthons

Journal

ORGANIC LETTERS
Volume 17, Issue 6, Pages 1461-1464

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.5b00339

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Funding

  1. Council for Chemical Sciences of The Netherlands Organization for Scientific Research (NWO/CW)

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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.

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