Photocatalytic Isomerization of Styrenyl Halides: Stereodivergent Synthesis of Functionalized Alkenes

Article abstract of DOI:10.1002/ejoc.201901119

An efficient and general method for the isomerization of styrenyl halides under different photocatalytic conditions (fac-Ir(ppy)₃ in methanol for E to Z isomerization and fluorescein in 1,4-dioxane for Z to E isomerization, respectively) is disclosed. A series of stereospecific transformations constitute preliminary validation of this strategy in the synthesis of functionalized alkenes, including two diaryl alkenes, a styrenyl boronic ester and an enyne. The photocatalytic isomerization and subsequent cross coupling reaction can be run in a one-pot manner. The stereodivergent synthesis of all four isomers of a conjugated diene, as well as the antitumor agent DMU-212 and its (Z)-isomer highlights the synthetic applicability of this method.