Palladium-Catalyzed Hydroarylation of N-Propargyl Benzamides: A Direct Route to N-Allylbenzamides and Acid-Induced Cyclization to Oxazolines

We have developed a palladium-catalyzed hydroarylation reaction as a highly efficient approach for accessing N-allylbenzamide derivatives in a more straightforward manner than conventional methods. Utilizing N-propargyl benzamides and boronic acids as key coupling partners, this strategy provides a diverse range of products in moderate to high yields, with electronic effect of boronic acids playing a crucial role in the reaction outcome. Notably, this method features a shorter and more practical synthetic sequence. Furthermore, we demonstrate its applicability in the synthesis of oxazoline derivatives through a convenient two-step process via acid-induced cyclization reaction.