Scandium(III)-Triflate-Catalyzed Pinacol-Pinacolone Rearrangement and Cyclization of 1,2-Diaryl-1,2-Ethanediol: A Versatile Synthesis of 1-Aryl-2,3-Dihydro-1H-3-Benzazepines

Abstract

An efficient scandium(III)-triflate-catalyzed pinacol-pinacolone rearrangement and cyclization of 1,2-diaryl-1,2-ethanediol has been developed, providing a variety of 2,3-dihydro-1H-3-benzazepine derivatives in good yields. The obtained products could be transformed to other valuable building blocks for the synthesis of some biologically active compounds or natural products. Moreover, this protocol was also successfully employed for the synthesis of the corresponding 1-phenyl-3,4,5,6-tetrahydrobenzo[d]azocine and 3-phenylisoquinoline products. © 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim