Unified Hydrogen Atom Transfer Approach To Construct Vicinal Functionality

Due to their prevalence in pharmaceuticals and natural products, vicinally functionalized motifs are highly sought-after. Traditionally, these fragments are synthesized from alkene precursors via oxidation reactions. However, complementary syntheses via a C-C bond-forming approach are underexplored. Herein, we disclose a unified approach for accessing these motifs by acetal reagents made from affordable, prefunctionalized starting materials. We have demonstrated the wide applicability of this methodology to a variety of molecularly complex substrates. Additionally, the coupled products can be employed in one-pot cyclizations to synthesize a variety of lactones.