We develop a palladium-catalyzed H/D exchange reaction with 8-aminoquinoline as the directing group as well as DO as the source of deuterium atom and solvent. This reaction achieves selectively H/D exchange at the ortho-C-H of aromatic amides and the β-C-H of aliphatic amide. Ortho-deuterated aromatic acids and β-deuterated aliphatic acids are obtained by removal of the directing group. And a possible mechanism is also proposed.
An efficient and simple synthesis of substituted 1H-pyrrole-3-carbonitriles was developed. This reaction is a palladium(II)-catalyzed cascade of C(sp)–C(sp2) coupling followed by intramolecular C–N bond formation. The method can tolerate various substrates with satisfactory yields. Its ligand-free conditions and high efficiency make this method particularly attractive.
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