Pd-Catalyzed Oxidative Aminocarbonylation of Arylboronic Acids with Unreactive Tertiary Amines via C-N Bond Activation

An efficient synthesis of tertiary amides from aryl boronic acids and inert tertiary amines through the oxidative carbonylation via C(sp(3))-N bond activation is presented. This protocol significantly restricts the homocoupling biarylketone product. It involves the use of a homogeneous PdCl2/CuI catalyst and a heterogeneous Pd/C based catalyst, which promotes C(sp(3))-N bond activation of tertiary amines with aryl boronic acids. This process represents a ligand-free, base-free, and recyclable catalyst along with an ideal oxidant like molecular oxygen.

Automated summary

An efficient method for synthesizing tertiary amides from aryl boronic acids and inert tertiary amines via oxidative carbonylation was presented, with significantly reduced homocoupling biarylketone formation. The use of homogeneous PdCl2/CuI and heterogeneous Pd/C catalysts promotes C(sp(3))-N bond activation between tertiary amines and aryl boronic acids, utilizing a ligand-free, base-free, and recyclable catalyst system with molecular oxygen as an ideal oxidant.