We report a Cu-catalyzed C−N cross-coupling of (hetero)aryl chlorides with a broad range of nitrogen nucleophiles. Nucleophiles include primary, secondary, and α-branched amines; amides; hydrazines; ammonia surrogates; NH-heterocycles; and base-sensitive substrates such as aminomethyl-functionalized azoles. Aryl and heteroaryl halides, including pyridyl and pyrimidyl chlorides, are competent reaction partners. Key reactivity trends of azole methanamines as a function of its azole identity and is