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

Highly regio- and stereoselective palladium-catalyzed ortho-vinylation of beta-naphthols (2) has been reported using easily accessible CF3-allyl carbonates (1). The regioselective nucleophilic gamma-attack of the CF3-pi-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.

Automated summary

A highly regio- and stereoselective palladium-catalyzed ortho-vinylation of beta-naphthols has been reported using accessible CF3-allyl carbonates, leading to the formation of (Z)-CF3-vinylnaphthols in good yields. Furthermore, a one-pot synthesis of CF3-naphtho[2,1-b]furans was achieved through an uninterrupted ortho-vinylation/oxidative radical cyclization reaction sequence.