Lithium Diisopropylamide Catalyzed Allylic C–H Bond Alkylation with Styrenes

Abstract

Allylic substitution reactions, a well-established approach for new bond construction, often need transition-metal catalysts and stoichiometric amounts of organometallic reagents, strong bases, or oxidants. Lithium diisopropylamide (LDA), a widely used and commercially available Brønsted base, is herein reported to catalyze the allylic C-H bond addition of 1,3-diarylpropenes to styrenes. Preliminary mechanism studies have provided a solid structure of the π-allyllithium intermediate and revealed the unique catalytic roles of LDA and its conjugate acid diisopropylamine.