Palladium-Catalyzed [1,3]-O-to-N Rearrangement of Allylic ­Imidates

Abstract

The rearrangement of allylic imidates is a powerful transformation for the synthesis of allylic amines. Whereas the [3,3]-rearrangement has long been established as the Overman rearrangement, the corresponding [1,3]-rearrangement is rare. Here, we report a novel strategy for the [1,3]-rearrangement of imidates based on the oxidative addition of a palladium(0) catalyst to an allylic imidate. Structurally distinct allylic amides could be synthesized under mild and base-free conditions.

Key words

palladium catalysis - allylic substitution - [1,3]-rearrangement - imidates - amides

Publication History

Received: 22 September 2021

Accepted after revision: 07 November 2021

Article published online:
17 November 2021

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