Water-mediated transition-metal-free Tsuji–Trost-type reaction

The treatment of 1-acetoxy-1,3-diphenylpropene (1) by C-, O-, S- and N-nucleophiles in basic aqueous media produced the corresponding substitution products in the absence of a transition-metal catalyst. Mechanistic studies, using (S)-1 and p-MeC6H4CH(OAc)CHCHPh as substrates, led to propose a BAL1 cleavage of the ester function leading to a stabilized allylic carbocation as intermediate.