The　development　of　persulfate-mediated　oxidation　of　tetrahydro-β-carbolines　is　reported.　This　mild　reaction　facilitates　the　formation　of　a　variety　of　2-formyl　N-substituted　tryptamines　and　the　related　derivatives　as　key　intermediates　in　moderate　to　excellent　yields.　The　method　is　applicable　to　direct　last-stage　oxidation　of　two　interesting　pharmaceuticals,　Cialis　and　evodiamine.　©　2019　American　Chemical　Society.