Login / Signup

Base-promoted triple cleavage of CCl 2 Br: a direct one-pot synthesis of unsymmetrical oxalamide derivatives.

Alageswaran JayaramVijay Thavasianandam SeenivasanKarthick GovindanYu-Ming LiuNian-Qi ChenTing-Wei YehGokulakannan VenkatachalamChien-Hung LiTsz-Fai LeungWei-Yu Lin
Published in: Chemical communications (Cambridge, England) (2024)
We present a novel, eco-friendly and one-pot approach for synthesizing unsymmetrical oxalamides with the aid of dichloroacetamide and amine/amides in the presence of CBr 4 in a basic medium. The use of water as a potent supplement for the oxygen atom source and the detailed mechanism have been disclosed. Moreover, the protocol involves triple cleavage of CCl 2 Br and the formation of new C-O/C-N bonds, with the advantage of achieving selective bromination using CBr 4 with good to excellent yield under mild conditions. The method also demonstrates promise for industrial use, as proven by its effective implementation in gram-scale synthesis conducted in a batch process, along with its utilization in a continuous-flow system.
Keyphrases