Photocatalytic annulative cyanoalkyletherification of 1,6-enynes toward 1-indanones

Abstract

A concise and operationally simple photocatalysis strategy for the annulative cyanoalkyletherification of 1,6-enynes with cyclic oxime esters and alcohols is reported, producing a set of functionalized 1-indanones bearing an all-carbon quaternary center with generally good yields. In this process, single electron reduction of cyclic oxime esters drives deconstructive carbon−carbon σ-bond cleavage to yield a key cyanopropyl radical poised for addition−cyclization. This reaction is redox-neutral and demonstrates good functional group compatibility and a wide substrate scope, in which diversified alcohols can be engaged in the annulation reaction to prepare exocyclic vinyl ethers.