Next, we also explored the reaction scope with respect to the aryl halides (Scheme 2). Aryl halides containing various functional groups efficiently underwent C-N coupling with n-butylamine, delivering the desired aryl C-N coupling products in generally high yields. Electron-rich aryl halides with para substituents such as Me (56), Bpin , SMe , OMe , and OCHF2 (60) exhibited high reactivity. Less reactive ortho-substituted aryl bromides also afforded the target products (74 and 75). Electron-deficient aryl halides were also suitable substrates for this red-light-driven C-N coupling reaction: products bearing a sulfoxide group , an unprotected sulfonamide (64), a ketone (65 and 66), a cyano group , a trifluoromethyl group (68), a halogen atom (69) could be obtained. Satisfactory yields were also obtained with multisubstituted aryl halides . Aryl halides with fused ring such as naphthalene , anthracene (77), fluorene , phenanthrene , or pyrene (81) also afforded the desired products in satisfactory yields. Aryl halides containing a heterocycle-such as pyridine , pyrimidine , pyrazine , quinoline , isoquinoline , quinoxaline , benzothiophene , thiophene , or carbazole (98)-were transformed into the corresponding heteroarylamines.