1,1-Regioselective alkenylboration of styrenes enabled by palladium catalysis

Despite the 1,2-difunctionalization reactions of styrenes have been well developed, the 1,1-regioselective addition reaction remains challenging. We disclose herein a palladium-catalyzed, highly 1,1-regioselective alkenylboration of styrenes by using alkenyl triflates and a diboron reagent as the coupling partners. A wide scope of styrenes derivatives and alkenyl triflates participate this reaction to provide the corre-sponding allyl boronates with high regioisomeric ratios. The success of this reaction is ascribed to the application of 1,10-phenanthroline-derivated ligand and the addition of ammonium chloride salt. More-over, acrylate esters can also selectively afford the 1,1-alkenylboration products under the same reaction conditions.& COPY; 2023 Published by Elsevier B.V. on behalf of Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences.

Automated summary

In this study, a highly 1,1-regioselective alkenylboration reaction of styrenes was achieved by using alkenyl triflates and a diboron reagent as the coupling partners. The reaction showed high synthetic reactivity for a wide range of styrene derivatives and alkenyl triflates. The success of this reaction was attributed to the application of a 1,10-phenanthroline-derived ligand and the addition of ammonium chloride salt. Additionally, acrylate esters could also selectively afford the 1,1-alkenylboration products under the same reaction conditions.