A rhodaelectro-catalyzed double dehydrogenative Heck reaction of indole-2-carboxylic acids with alkenes has been developed for the synthesis of pyrano[3,4-b]indol-1(9H)-ones. The weakly coordinating carboxyl group is utilized twice as a directing group to activate the C-H bonds throughout the reaction. This reaction precedes an acceptorless dehydrogenation under exogenous oxidant-free conditions in an undivided cell with a constant current.