Addition of the tertiary radicals to electron-deficient 1,3-dienes using photoredox catalysis

Abstract

The tertiary carbon radicals were created by an Ir-catalyzed photocatalyst. The addition of the created radicals to different substituted electron-deficient 1,3-dienes was carried out. New carbon centers append δ-substituted-β,γ-unsaturated scaffold were constructed through the 1,6-addition of tertiary carbon radicals to alkyl penta-2,4-dienoate derivatives or hexa-3,5-dien-2-one derivatives. Unlike the latter dienes, addition tertiary carbon radicals to cyclic ketonic electron-deficient dienes produced conjugated cycloalkenone. In each case, the stereoisomer majority was E stereoisomer while Z stereoisomer was observed as trace amounts.