Regioselective Synthesis of Benzo-Fused Tetrahydroisoquinoline-Based Biaryls through a Tandem One-Pot Halogenation of p-Benzynes from Enediynes and Suzuki-Miyaura Coupling
2019
Das, Eshani | Basak, Amit
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%).
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