University Honors

Nitrile functional groups (CN) are prevalent in pharmaceuticals, bioactive compounds, and materials. However, conventional methods for incorporating nitrile groups often require toxic cyanide sources. In response to this, alternative cyanide sources have been developed, although many alternatives form toxic hydrogen cyanide (HCN) during workup or in situ. Herein we report a novel method for cyanation utilizing benzonitriles as non-toxic cyanide donors enabled by nickel (Ni) catalysis for the formation of new C-CN bonds. This work describes the activation of cyclopropyl ketones which undergo tandem ring-opening cyanation to yield δ-Keto Nitriles. Optimization of this reaction is achieved through fine tuning the reaction conditions, including substrate variations and screening of ligands to maximize yield and selectivity. Additional research is required to gain mechanistic insights, which will be pursued through kinetic studies and synthesis of key reaction intermediates. Improved mechanistic understanding is anticipated to provide valuable information on C-CN activation, advancing cyanation techniques and their utility in chemical synthesis and industrial applications.