Over 80% of the pharmaceuticals currently on the market contain at least one carbon-nitrogen bond, as do many important biomolecules. Thus, methods that enable chemists to introduce nitrogen into a broad range of hydrocarbon feedstocks in an efficient, atom-economical, and environmentally friendly manner is of intense interest to the community. In particular, the prevalence of carbon-hydrogen bonds in organic molecules make them ideal targets for functionalization to furnish more valuable compounds. However, achieving this goal presents a number of challenges, including the strength and relative inertness of the C–H bond, the number of C–H bonds present in many building blocks, and the difficulty of targeting a specific site for installation of a new C–N bond. In this talk, I describe our group’s efforts to harness unusual features of silver coordination complexes to catalyze nitrene transfer reactions capable of transforming specific C–H bonds to C–N bonds in a tunable manner. Selected design principles underlying the ability to alter the chemo-, site-, and enantioselectivity of C–H bond amidations will be presented and examples for the late-stage functionalization of medicinally relevant molecules highlighted. Computational efforts to develop predictive models for selectivity and extension of these design principles to other metals and other C–H functionalizations will also be described.

Tunable and predictable chemocatalyzed site- and enantioselective C–H functionalizations

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