Meyer-Schuster-Type Rearrangement of Propargylic Alcohols into α-Selenoenals and -enones with Diselenides

We describe a mild and broadly applicable protocol for the preparation of a diverse array of multisubstituted alpha-selenoenals and -enones from readily accessible propargylic alcohols and diselenides. The transformation proceeds via the Selectfluor-promoted selenirenium pathway, which enables selenenylation/rearrangement of a variety of propargylic alcohols. Gram-scale experiments showed the potential of this synergistic protocol for practical application.

Automated summary

The mild and broadly applicable protocol described enables the preparation of a diverse array of multisubstituted alpha-selenoenals and -enones from easily accessible propargylic alcohols and diselenides. The transformation proceeds via the Selectfluor-promoted selenirenium pathway, showing potential for practical application in gram-scale experiments.