Abstract
An intermolecular radical addition, using photoredox catalysis, to allenamides and allencarbamates is reported. This transformation synthesizes N-acyl-N’-aryl-N,N’-allylaminals, and proceeds by a conjugated N-acyliminium intermediate that previously has principally been generated by electrophilic activation methods. The radical adds to the central carbon of the allene giving a conjugated N-acyliminium that undergoes nucleophilic addition by arylamines and alcohols.
Highlights
Allenamides (Scheme 1, 1) and their congeners have attracted considerable attention over the past 15 years due to their characteristic reactivity profiles [1,2,3,4]
The reaction of the allenamide with an electrophilic source promotes the formation of a conjugated N-acyliminium intermediate 2
We envisaged that a route to the conjugated N-acyliminium intermediate could be achieved via an intermolecular addition of an electrophilic radical to an allenamide (1) followed by an oxidation process on the subsequently formed radical (Scheme 3) [41]
Summary
Allenamides (Scheme 1, 1) and their congeners have attracted considerable attention over the past 15 years due to their characteristic reactivity profiles [1,2,3,4]. The reaction of the allenamide with an electrophilic source promotes the formation of a conjugated N-acyliminium intermediate 2 The allenamide building block we sought a new synthetic methodology that could generate this conjugated N-acyliminium intermediate 2, that would not be dependent on conventional electrophilic activation modes (Scheme 2).
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