Ceric ammonium nitrate impregnated on silica gel in the removal of the tert-butoxycarbonyl group

Abstract

The tert-butoxycarbonyl group was efficiently (80-99% yields) removed from an amino, hydroxy, or mercapto functionality in organic compounds by use of 0.20 equiv of Ce(NH 4 ) 2 (NO 3 ) 6 in acetonitrile at reflux. Application of the solid-supported reagent involving the use of 0.20 equiv of Ce(NH 4 ) 2 (NO 3 ) 6 impregnated on silica gel in toluene at reflux gave the deprotected products in 90-99% yields. These reactions likely proceed through an electron transfer process.