Ligand-Controlled Nickel-Catalyzed Reactions of Benzocyclobutenones with Alkynyltrifluoroborates: Diverse Construction of Polysubstituted Naphthols

Abstract

Ligand-controlled nickel-catalyzed selective cleavage of the C1–C2 or C1–C8 bond of benzocyclobutenones (BCBs) is reported. The delicate selection of dpppe or PMe3 as the ligand led to predictably divergent synthesis of a wide range of 1-naphthols and 2-naphthols without C2 and C3 substituents, respectively, from BCBs and potassium alkynyltrifluoroborate, and the increase in the amount of PMe3 resulted in tandem reaction of 2 equiv of BCB with the borate to afford 3,4,5-trisubstituted 2-naphthols. The fabulous ligand effect resulted in the facile and unique construction of multisubstituted naphthols with well-controlled regioselectivity and a high degree of structural diversity.

Alkaline-Metal-Promoted Divergent Synthesis of 1-Aminoisoquinolines and Isoquinolines

“…Recently, Verma’s group reported t -BuOK-mediated versatile cascade dual-annulation for the construction of benzo[ c ]phenanthridines and benzo[ c ]phenanthrolines . As a continuation of our studies on the applications of methyl and carbonyl compounds, we herein report the alkaline-metal-promoted three-component reactions for isoquinoline synthesis, in which this protocol provides a simple and efficient method for the synthesis of 1-aminoisoquinolines and isoquinolines from easily available starting materials (Scheme e).…”