Palladium-Catalyzed Prenylation Of (Hetero)Aryl Boronic Acids

Prenyl or dimethylallyl groups are common structural motifs in natural products and small molecule therapeutics. In this report, we describe a palladium-catalyzed method for the cross-coupling of aryl and heteroaryl boronic acids with prenyl alcohol. Catalyst systems based on dialkylbiaryl phosphines were highly active for this transformation. These supporting ligands provided opportunities for tuning the efficiency and regioselectivity of carbon-carbon bond formation. In addition, this method was further extended to the cross-coupling of symmetrical allylic alcohols with aryl boronic acids. (C) 2021 The Authors. Published by Elsevier Ltd.