Cu/Fe-Cocatalyzed Meyer–Schuster-like Rearrangement of Propargylic Amines: Direct Access to E‑β-Aminoacryaldehydes

A simple and efficient method for the synthesis of β-aminoacryaldehydes via Cu­(OAc)2·H2O and FeCl3 cocatalyzed Meyer–Schuster-Like rearrangement of propargylic amines was developed. The reactions proceed selectively as the E-isomers in generally good yields under aerobic conditions, and are compatible with a broad range of functional groups. This method combines C–N bond cleavage as well as the N-aryl group migration and provides a practical and mild synthetic approach to α,β-unsaturated carbonyl compounds, which are useful precursors in a variety of functional group transformations.