American Chemical Society
ol1c01594_si_001.pdf (6.95 MB)

Assembly of Tetrahydroquinolines and 2‑Benzazepines by Pd-Catalyzed Cycloadditions Involving the Activation of C(sp3)–H Bonds

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journal contribution
posted on 2021-06-24, 19:22 authored by Xandro Vidal, José Luis Mascareñas, Moisés Gulías
Cycloaddition reactions are among the most practical strategies to assemble cyclic products; however, they usually require the presence of reactive functional groups in the reactants. Here, we report a palladium-catalyzed formal (4 + 2) cycloaddition that involves the activation of C­(sp3)–H bonds and provides a direct, unconventional entry to tetrahydroquinoline skeletons. The reaction utilizes amidotolyl precursors and allenes as annulation partners, and is catalyzed by Pd­(II) precursors in combination with specific N-acetylated amino acid ligands. The reactivity can be extended to ortho-methyl benzylamides, which provide for the assembly of appealing tetrahydro-2-benzazepines in a formal (5 + 2) annulation process.