Synthesis of Silylated Azauracil 1-Oxides by Metal-Free Direct Silylation

Abstract A direct C–H silylation strategy is reported for synthesizing silylated derivatives of azauracil 1-oxide in a simple and environmentally benign way under metal-free conditions using triphenylsilane as a silyl precursor and TBHP as an oxidant. This methodology is useful for late-stage modification of various bioactive molecules, such as ibuprofen and gemfibrozil. A mechanistic investigation suggested that the reaction proceeds through a radical pathway.