In order to improve the scalability of the C1-selective benzylic oxidation, conditions involving the generation of a tertbutoxy radical from various metal salts were investigated. It was determined that treatment of 3-1 with catalytic Mn(OAc)3 in the presence of excess t-BuOOH provided 9-1 in 33% 1 H-NMR yield, which was ultimately the most scalable set of conditions. On two-gram scale, 9-1 was obtained in 34% yield along with 47% of the recovered starting material (3-1). Altering the metal salt had little effect on the yield (Scheme 9, Table ). Stahl's Co-catalyzed oxidation system 45 resulted in a good yield of 9-1, whereas the Cu-catalyzed system 46 only gave decomposition (see Supporting Information Scheme SI1 for more details). Utilizing Pd(OAc)2 and benzoquinone or Van Humbeck's conditions 47 failed to form any desired product. Additional established strategies to oxidize the benzylic position of heterocycles, such as SeO2, IBX, 48 or other Cr-based oxidants, resulted in poor conversion and decomposition.