Palladium-catalyzed oxidative annulation of N-(8-quinolinyl) aryl carboxamides with 1-aryl-2-tosyloxy ethanones

Abstract

A novel and facile palladium-catalyzed annulation reaction between N-(8-quinolinyl) aryl carboxamides and 1-aryl-2-tosyloxy ethanones was herein demonstrated. The practical transformation took place readily in the presence of Pd(OAc)₂ without any ligands, offering the desired 3-aryl-2-(8-quinolinyl) isoquinolin-1(2H)-ones with good functional groups tolerance (29 examples) and high efficiencies (up to 90% yields). The mechanism of the protocol was proposed to take place through a C-H/N-H activation pathway, which was verified by the control reactions.

Graphical Abstract

Keywords:

• Palladium-catalysis
• annulation reaction
• N-(8-quinolinyl) carboxamides
• 1-aryl-2-tosyloxy ethanones
• 3-aryl-2-(8-quinolinyl) isoquinolin-1(2H)-ones

Acknowledgments

The authors are grateful for the financial support from the National Natural Science Foundation of China (NSFC) (grant number 21806033).