The production of organoboronic ester derivatives is becoming increasingly important in modern organic synthesis due to their versatility in forming C-C bonds by Suzuki-Miyaura cross-coupling reactions. The goal of this research is to synthesize a pinacolborane- substituted diene by the 9-BBN catalyzed hydroboration of the enyne (E)-but-1-en-3-yn-1-ylbenzene. This hydroboration reaction is of special interest because there are two potentially reactive sites (i.e. an alkene and alkyne). Therefore, the opportunity to develop a novel and selective method for the preparation of this class of compounds exists. In addition, the product would be of high synthetic utility in the reactions of dienes (Diels-Alder) and boronic esters (Suzuki-Miyaura). Here we present our research on the synthesis of 4,4,5,5-tetramethyl-2-((1E,3E)- 4-phenylbuta-1,3-dien-1-yl)-1,3,2-dioxaborolane by the 9-BBN catalyzed hydroboration of (E)-but-1-en-3-yn-1-ylbenzene.
