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

Abstract

Highly regio- and stereoselective palladium-catalyzed ortho-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 (Z)-CF₃-vinylnaphthols (3) in good yields. Furthermore, we achieved a one-pot synthesis of CF₃-naphtho[2,1-b]furans (4) through an uninterrupted ortho-vinylation/oxidative radical cyclization reaction sequence.