Boron-catalysed transition-metal-free arylation and alkenylation of allylic alcohols with boronic acids

Abstract

The development of efficient catalytic reactions with excellent atom and step economy employing sustainable catalysts is highly sought-after in chemical synthesis to reduce the negative effects on the environment. The most commonly-used strategy to construct allylic compounds relies on the transition-metal-catalysed nucleophilic substitution reaction of allylic alcohol derivatives. These syntheses exhibit good yield and selectivity, albeit at the expense of toxic and expensive catalysts and extra steps. In this paper, we report a transition-metal-free arylation and alkenylation reaction between unprotected allylic alcohols and boronic acids. The reactions were performed with B(C₆F₅)₃ as the catalyst in toluene, and corresponding products were obtained in 23–92% yields. The reaction has mild conditions, scalability, excellent atom and step economy.