Palladium-catalyzed anti-Markovnikov oxidative acetalization of activated olefins with iron(iii) sulphate as the reoxidant?

Organic & Biomolecular Chemistry Pub Date: 2021-12-10 DOI: 10.1039/D1OB02227J

Abstract

This paper discloses the efficient palladium-catalyzed anti-Markovnikov oxidative acetalization of activated terminal olefins with iron(III) sulfate as the reoxidant. This methodology requires mild reaction conditions and shows high regioselectivity toward anti-Markovnikov products and compatibility with a wide range of functional groups. Iron(III) sulphate was the sole reoxidant used in this method. Various olefins like vinylarenes, aryl-allylethers, aryl or benzyl acrylates and homoallylic alcohols all reacted well providing anti-Markovnikov acetals, some of which represent orthogonally functionalized 1,3- and 1,4-dioxygenated compounds.

Graphical abstract: Palladium-catalyzed anti-Markovnikov oxidative acetalization of activated olefins with iron(iii) sulphate as the reoxidant
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