KEY C–C DISCONNECTIONS REALIZED VIA SITE-SELECTIVE AMIDYL RADICAL MEDIATED C–H FUNCTIONALIZATION

I. Intermolecular Aliphatic C–H Functionalization as a Synthetic ToolSite-selective intermolecular aliphatic C–H functionalization provides unique approaches for accessing unique molecules primed for studies in late-stage functionalization or for further use as building blocks. Several platforms have been developed for such an approach, but methods still remain rather limited. The use of amidyl radicals has proven to be an effective platform for C–H functionalization, and the development of new reactions is of paramount importance. II. Strategic Applications of C–H Functionalization for Late-Stage C–C bond formation Methods that access unique C–C disconnections by C–H functionalization are highly sought in regard to the exploration of new chemical space. Despite the need for new reactions that form these bonds, there are few methods available for the concise site-selective introduction of functional groups bearing a C–C bond. Here, we disclose the development of strategies involving amidyl radical mediated C–H functionalization as our key step to afford unique disconnections relevant in late-stage functionalization and building block synthesis. III. Intermolecular Aliphatic C–H Heteroarylation with Amidyl Radicals Here we disclose the concise introduction of heteroarenes in a site-selective manner using an O-alkenyl hydroxamate and readily accessed heteroaryl sulfones. Notable in these studies is the use of substrate as limiting in all cases, which makes this transformations suitable for late-stage functionalization of complex molecules. IV. Vicinal Aliphatic C(Sp3)–H Functionalization for the Construction of Fused Cyclobutanols Approaches for the dual functionalization of vicinal C–H bonds are highly regarded as effective means for decorating molecules with dense functionality and complexity. Here, we disclose the formation of cyclobutanols employing site-selective intermolecular C–H functionalization and specially designed alkenyl carbonate radical acceptors.