Palladium-catalyzed<i>ortho</i>-vinylation of β-naphthols with α-trifluoromethyl allyl carbonates: one-pot access to naphtho[2,1-<i>b</i>]furans

Abstract

Highly regio- and stereoselective palladium-catalyzed <i>ortho</i>-vinylation of β-naphthols (2) has been reported using easily accessible CF₃-allyl carbonates (1). The regioselective nucleophilic γ-attack of the CF₃-π-allyl-Pd-intermediate is the key to furnish (<i>Z</i>)-CF₃-vinylnaphthols (3) in good yields. Furthermore, we achieved a one-pot synthesis of CF₃-naphtho[2,1-<i>b</i>]furans (4) through an uninterrupted <i>ortho</i>-vinylation/oxidative radical cyclization reaction sequence.