2-Benzamide Tellurenyl Iodides: Synthesis and Their Catalytic Role in CO 2 Mitigation

• Published in: Chemistry : a European journal 2023-09, Vol.29 (49), p.e202301502
• Main Authors: Jain, Saket, Batabyal, Monojit, Thorat, Raviraj Ananda, Choudhary, Pratibha, Jha, Raushan Kumar, Kumar, Sangit
• Format: Article
• Language: English
• ISSN: 0947-6539; 1521-3765
• DOI: 10.1002/chem.202301502

Benzamide-derived organochalcogens (chalcogen=S, Se, and Te) have shown promising interest in biological and synthetic chemistry. Ebselen molecule derived from benzamide moiety is the most studied organoselenium. However, its heavier congener organotellurium is under-explored. Here, an efficient copper-catalyzed atom economical synthetic method has been developed to synthesize 2-phenyl-benzamide tellurenyl iodides by inserting a tellurium atom into carbon-iodine bond of 2-iodobenzamides in one pot with 78-95 % yields. Further, the Lewis acidic nature of Te center and Lewis basic nature of nitrogen of the synthesized 2-Iodo-N-(quinolin-8-yl)benzamide tellurenyl iodides enabled them as pre-catalyst for the activation of epoxide with CO at 1 atm for the preparation of cyclic carbonates with TOF and TON values of 1447 h and 4343, respectively, under solvent-free conditions. In addition, 2-iodo-N-(quinolin-8-yl)benzamide tellurenyl iodides have also been used as pre-catalyst for activating anilines and CO to form a variety of 1,3-diaryl ureas up to 95 % yield. The mechanistic investigation for CO mitigation is done by Te NMR and HRMS studies. It seems that the reaction proceeds via formation of catalytically active Te-N heterocycle, an ebtellur intermediate which is isolated and structurally characterized.