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

Xandro Vidal | Zendy; José L. Mascareñas | Zendy; Moisés Gulı́as | Zendy

Open Access

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

Author(s) -

Xandro Vidal,

José L. Mascareñas,

Moisés Gulı́as

Publication year - 2021

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.1c01594

Subject(s) - annulation , chemistry , benzazepines , cycloaddition , catalysis , combinatorial chemistry , reactivity (psychology) , palladium , stereochemistry , bicyclic molecule , medicinal chemistry , organic chemistry , medicine , alternative medicine , pathology

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(sp 3 )-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.

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