Indoles are not indolent : Various indoles react with arylboronic acids chemodivergently. C? H arylation of free indole and N‐methylindole gives the corresponding C(2)‐arylated indoles A whereas N‐acylated, N‐benzoylated, and N‐Boc‐protected indoles provide the corresponding arylcarboaminoxylated products B with excellent diastereoselectivity in good to excellent yields.