Meyer–Schuster-Type Rearrangement of Propargylic Alcohols into α-Selenoenals and -enones with Diselenides
Yong‐Liang Ban, Long You, Kaiwen Feng, Fei-Cen Ma, Xiaoling Jin, Qiang Liu
Abstract
We describe a mild and broadly applicable protocol for the preparation of a diverse array of multisubstituted α-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.
Topics & Concepts
ChemistrySelectfluorCombinatorial chemistryTransformation (genetics)Organic chemistryStereochemistryCatalysisBiochemistryGeneOrganoselenium and organotellurium chemistrySulfur-Based Synthesis TechniquesCatalytic Alkyne Reactions