Palladium-catalyzed ortho-vinylation of β-naphthols with α-trifluoromethyl allyl carbonates: one-pot access to naphtho[2, 1-b]furans. Issue 38 (10th September 2021)

• Record Type: Journal Article
• Authors: Priyanka, Chiliveru; Subbarao, Muppidi; Punna, Nagender
• Is Part Of: Organic & biomolecular chemistry. Volume 19:Issue 38(2021)
• Page Start: 8241
• Page End: 8245
• Publication Date: 2021-09-10
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d1ob01429c
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : Highly regio- and stereoselective ortho -vinylation of β-naphthols has been accomplished via CF3 –π-allyl Pd-complex for the first time. Next, one-pot synthesis of CF3 -naphtho[2, 1- b ]furans is developed through a oxidative radical cyclization reaction. 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.