Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 19, Issue 38, Pages 8241-8245Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d1ob01429c
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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.
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.
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