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.