In this laboratory experiment, upper-division undergraduate chemistry and biochemistry majors investigate amide-bond-forming reactions from a green chemistry perspective. Using hydrocinnamic acid and benzylamine as reactants, students perform three types of amide-forming reactions: an acid chloride derivative route; a coupling reagent promoted method; and a boric acid catalyzed condensation. After isolation of the common product, students assess the reactions using the 12 Principles of Green Chemistry and several green chemistry metrics: atom economy; reaction mass efficiency; process mass intensity; and the EcoScale. In addition to assessing what route is the greenest, students also compare the metrics to discern what aspects of green chemistry each metric captures. In order to extend sustainability to economic considerations, the projected "front-end" cost of synthesizing a kilogram of the amide is calculated based on data from each reaction. The experimental work is conducted over two 3 h laboratory periods.

Hypervalent iodine­(V) reagents are a powerful class of organic oxidants. While the use of I­(V) compounds Dess–Martin periodinane and IBX is widespread, this reagent class has long been plagued by issues of solubility and stability. Extensive effort has been made for derivatizing these scaffolds to modulate reactivity and physical properties but considerable room for innovation still exists. Herein, we describe the preparation, thermal stability, optimized geometries, and synthetic utility of an emerging class of I­(V) reagents, Bi­(N)-HVIs, possessing datively bound bidentate nitrogen ligands on the iodine center. Bi­(N)-HVIs display favorable safety profiles, improved solubility, and comparable to superior oxidative reactivity relative to common I­(V) reagents. The highly modular synthesis and in situ generation of Bi­(N)-HVIs provides a novel and convenient screening platform for I­(V) reagent and reaction development.