Aerobic Allylation of Alcohols with Non-Activated Alkenes Enabled by Light-Driven Selenium-π-Acid Catalysis

Abstract

A new organocatalytic protocol for the aerobic dehydrogenative allylation of alcohols using non-activated alkenes as the allylating reagent and ambient air as the terminal oxidant is established. Mechanistically, the procedure relies on the interplay of a diselane and a photo­redox catalyst by means of a light-induced electron transfer process. Under optimized conditions, a broad range of both cyclic and acyclic ethers is accessed with very high functional group tolerance and excellent regioselectivity.

Key words

alcohols - allylations - alkenes - oxidations - photoredox catalysis - selenium-π-acids

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