1,3-Butadiene Dicarbofunctionalization Enabled by the Dual Role of Diaryl Ketone in Photo-HAT/Chromium Catalysis

Abstract

We report a three-component Nozaki–Hiyama–Kishi type reaction of 1,3-dioxolane, 1,3-butadienes, and aldehydes to access masked aldehyde-incorporated homoallylic alcohols, facilitated by photo-hydrogen atom transfer (HAT)/chromium dual catalysis. The diaryl ketone serves dual roles both in the HAT process and in facilitating the turnover of the chromium catalyst. A range of functional groups are tolerated owing to the mild conditions. Both aromatic and aliphatic aldehydes are suitable substrates for coupling with several 1,3-butadienes and 1,3-dioxolane.

Functionalization of 1,3‐Butadiene Derivatives under Photo/Electrocatalysis

“…This transformation was achieved by utilizing 1,3-butadienes, 1,3-dioxolane, and aldehydes as the primary reagents, as illustrated in Scheme 21. [33] The presence of ligand, chromium catalyst, and an inert atmosphere proved to be indispensable for the successful execution of the reaction, as no conversion was detected in the absence of any of these components. The desired products were obtained in satisfactory to excellent yields and displayed moderate to good diastereoselectivities, utilizing both aliphatic and aromatic aldehydes as the starting materials.…”