The rapid synthesis of the isoindolinone skeleton has been accomplished by a palladium‐catalyzed one‐pot tandem process, which consists of an isocyanide insertion/hydration (carboxamidation) and 5‐exo‐dig cycloisomerization (hydroamidation) reaction sequence that afforded the products in good to excellent yields. Preliminary mechanistic studies of this sequential C–C/C–O/C–N bond formation process suggests that the carboxamidation step is palladium‐dependent, whereas the hydroamidation step is solely mediated by the base and is driven by the electrophilicity of the alkyne.
A metal free approach to access congested aryl amines using aza-oxyallyl cations as electrophiles has been reported. The given method could readily be adapted for the synthesis of coveted 3,5-benzodizepinones.
Herein,
we report a highly efficient and unprecedented
approach
for heteroarylation of congested α-bromoamides via electrophilic
aromatic substitution of imidazo-heteroarenes and indolizines under
mild reaction conditions (room temperature, metal, and oxidant free).
The participation of an in situ generated aza-oxyallyl cation as an
alkylating agent is the hallmark of this transformation. The method
was readily adapted to synthesize novel imidazo-heteroarene-fused
dibenzoazepinone architectures of potential medicinal value.
Correction for ‘Pd-Catalysed [3 + 2]-cycloaddition towards the generation of bioactive bis-heterocycles/identification of COX-2 inhibitors via in silico analysis’ by Elagandhula Sathish et al., Org. Biomol. Chem., 2022, 20, 4746–4752, https://doi.org/10.1039/D2OB00467D.
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