Regioselective Synthesis of Benzo-Fused Tetrahydroisoquinoline-Based Biaryls through a Tandem One-Pot Halogenation of p-Benzynes from Enediynes and Suzuki-Miyaura Coupling.

Abstract

A regioselective halogenation of p-benzyne derived from a nonaromatic enediyne core via Bergman cyclization and Suzuki-Miyaura coupling of the resulting haloarene in one-pot is disclosed. For the one-pot protocol to work, the reaction conditions were modified compared to an earlier reported procedure ( J. Org. Chem. 2019 , 84 , 2911 - 2921 ) by reducing the amount of lithium iodide and exclusion of pivalic acid. Under these modified conditions, the products, benzo-fused tetrahydroisoquinoline-based biaryl derivatives were obtained in overall high to excellent yields (71-90%).