Herein, we report a method that uses antifungal tavaborole as a co-catalyst for direct α-C–H alkylation of structurally diverse alcohols through photoredox catalysis. The protocol features mild conditions, remarkable scope, and wide functional group tolerance, which allows for the construction of a wide array of highly functionalized alcohols, including homoserine derivatives and C-glycosyl amino acids. We also demonstrate the synthetic applications of this methodology to the late-stage functionalization of pharmaceuticals and natural products.

Herein, we report a distinctive photoredox/copper dual-catalyzed esterification of benzylic C–H bonds through the combination of photoredox-mediated hydrogen atom transfer and Cu­(II)-mediated radical-polar crossover. This methodology demonstrates a high functional group tolerance (>40 examples) and moderate to good yields with structurally diverse benzylic C–H substrates. Notably, stoichiometric amounts of carboxylic acids are used as coupling partners, which allows the synthesis of structurally diverse benzylic esters and the late-stage functionalization of pharmaceuticals.

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