The prevalent use of C(sp2)-hybridized reagents in traditional cross-coupling reactions has resulted in largely "flat" compounds and contributed to a growing demand of three-dimensionality in compound libraries. C(sp3)–H bonds adjacent to aromatic rings are ubiquitous moieties in medicinally relevant building blocks. These benzylic C(sp3)–H bonds are intrinsically reactive and represent a wealth of opportunities for C–H functionalization and synthesis of three-dimensional (3D) structures. Recent advances in Cu-catalyzed radical relay chemistry have enabled site-selective functionalization of benzylic C(sp3)–H bonds with the C–H substrate as the limiting reagent, yet cross coupling reactions of this type remained largely underexplored. This talk will disclose the development of radical relay Cu-catalyzed benzylic C(sp3)–H cross-coupling methods, enabled by a "redox buffering" strategy, and their applications in synthesis of drug-like 3D molecules.

Copper-catalyzed benzylic C(sp3)–H cross couplings: Methodology development and applications in medicinal chemistry

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ACS Fall 2022

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