Imines are well known, important functional groups with varying applications in both the material and biological science fields. The formation of the desired imine product is difficult to achieve through normal amine condensation reactions, requiring harsh conditions, this begs the question if the same result can be achieved through a more mild condition, more tolerant of sequential reactions and sensitive starting materials. Currently, the reaction of diazo compounds and azides is the preferred reaction pathway; this is due to the high energy of the two starting materials, leading to an increased reactivity. In a recent study, activation of the azide allowed for the formation of a reactive Rhodium-nitrene intermediate. While this route for the production of the imine product was sufficient, the proposed reaction path brought about questions for the difference in reactivity between the Rh(II) and Au(I) preferred pathways. Our groups recent work with α-diazoester Au(I) catalyzed reactions showed that Au(I) has the ability to form a “carbophilic cation”, this compound possesses the ability for ligand controlled chemoselectivity, preforming site selective Friedel- Craft like additions. This previous work leads to the thought process that the gold carbenoid intermediate will be much the same, and that the increased reactivity would therefore allow for a more favorable condition through fine tuning, thus presenting the opportunity for a sequential reaction. The difference in the formation of the two transition species leads to the inquiry for the comprehensive investigation of the reactivity and selectivity differences in the gold carbenoid and rhodium nitrene chemistry. The preliminary results from our comparative investigation, has shown gold to have a higher reactivity forming the desired imine product in &gt;75% yields. With these results, we have begun to investigate the scope and screen possible sequential reactions.

Au(I) catalyzed imine formation from α-diazoesters and azide

249th National Meeting (2015)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.