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

Org Biomol Chem. 2021 Oct 6;19(38):8241-8245. doi: 10.1039/d1ob01429c.

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.