Supported-Pd catalyzed tandem approach for N-arylbenzamides synthesis

• DOI: 10.1016/j.mcat.2021.111948
• Publication Date: 2021-11-21T20:14:55Z
• Authors: Sheetal; Ajay Kumar Sharma; Shaifali; Dhananjay Bhattac...; Navneet Sharma; Kousik Giri; Pralay Das
• Keywords: Sodium azide; Tandem; Carbonylation; Cascade reaction; Protonolysis

Abstract Aryl iodides as dual arylating agent for C-terminal from oxalic acid [(CO2H)2] and N-terminal from sodium azide (NaN3) for N-aryl benzamides (Ar-CO-NH-Ar) synthesis is a rare invention which has been attempted successfully under this study. A single step tandem approach for the synthesis of N-aryl benzamides has been developed through bifunctional transformation of aryl iodides with in-situ CO from (CO2H)2 and NaN3 following two different pathways of carbonylation and azidation. The polystyrene supported palladium (Pd@PS) catalyst was found to be well compatible to perform the domino-reaction in a double layer vial (DLV) system under base, ligand and additive-free conditions. Moreover, the same approach was further extended with aryl azides for unsymmetric N-aryl benzamides (Ar-CO-NH-Ar') synthesis. Furthermore, the DFT studies were also performed to support the proposed mechanism.