A mild procedure for C-7-selective C-H alkenylation of various indolines under oxidative palladium(II) catalysis is reported. A fully substituted urea, formed by carbamoylation of the indoline nitrogen atom, functions as a directing group. Both α,β-unsaturated acceptors and styrenes participate in this direct C-H functionalization. With a free NH group at the urea terminus, the nitrogen atom subsequently cyclizes in a 1,4-fashion to yield a six-membered ring.