Copper-catalyzed intermolecular carboamination of alkenes with alpha-halocarbonyls and amines is presented with 42 examples. Electron rich, electron poor, and internal styrenes, as well as alpha-olefins, are function-alized with alpha-halocarbonyls and aryl or aliphatic amines. Mechanistic investigations suggest the reaction is proceeding through addition of a carbon-centered radical across an olefin followed by oxidation to form a 5-membered oxocarbenium intermediate and subsequent nucleophilic ring opening to forge the C-N bond.