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

In the present investigation, systematic study of the reaction of tertiary alcohol-derived carbon radicals with 1,3-dienes was carried out. Using this chemistry, I was able to prepare a series of alkenes that contain complex quaternary carbon fragments. This reaction can be easily utilizing in many cases where tertiary alcohol precursor is more readily available than the corresponding halide precursor. [Display omitted] • Synthesis of precursors of tertiary radicals. • Synthesis of electron-deficient 1,3-dienes. • Tertiary carbon radicals were generated by an Ir-catalyzed visible-light photocatalyst. • Addition of tertiary carbon radicals to electron-deficient 1,3-dienes was carried out. 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. [ABSTRACT FROM AUTHOR]