Iridium-catalyzed ortho-selective carbon–hydrogen amidation of benzamides with sulfonyl azides in ionic liquid

Abstract

Ir-catalyzed ortho-C–H amidation of benzamides with sulfonyl azides has been conducted effectively in ionic liquid reaction medium.

Recent advances in metal directed C–H amidation/amination using sulfonyl azides and phosphoryl azides

“…Notably, studies have concentrated on the utilization of deep eutectic solvents (DES) and ionic liquids (ILs), which are environmentally safe and can be recycled. 17,34,122…”

“…In a 2020 publication by L.-Y. Jiao et al , 34 a new synthetic approach was developed for preparing sulfonamide compounds. This method involved the ortho -selective carbon–hydrogen (C–H) amidation of benzamides using sulfonyl azides as nitrogen sources, facilitated by an iridium catalyst.…”

“…Once again, the iridium complex catalyst demonstrates its catalytic activity not only in nonpolar solvent media but also in highly polar media such as ionic liquids. 34 In a recent contribution by Ning et al (2021), 192 a novel synthetic methodology was developed for the production of phosphoramides via iridium-catalyzed C–H amidation of benzamides with phosphoryl azides in ionic liquids. This study introduces a direct, efficient, and environmentally friendly strategy for catalyzing the conversion of C–H bonds into amides using a transition metal iridium catalyst.…”

“…Notably, iridium catalysts have demonstrated effectiveness in the direct C-H amination of unactivated arenes using phosphoryl azides as nitrogen sources. [32][33][34][35][36] In summary, the choice of a metal catalyst for directed C-H amination depends on various factors, including the substrate, the desired product, and the reaction conditions. To gain a better understanding of metal-mediated C-H activation chemistry, it is essential to establish precise definitions for key terms commonly encountered in this field before delving deeper into the discussion.…”

“…Notably, studies have concentrated on the utilization of deep eutectic solvents (DES) and ionic liquids (ILs), which are environmentally safe and can be recycled. 17,34,122 In addition the challenge of functional group tolerance represents a significant hurdle in advancing C-H functionalization methods. Pharmaceuticals and natural products often contain a diverse array of functional motifs, which can potentially create challenges for transition metal-catalyzed reactions.…”