Table 2.

Amine Scope of the Dearomative syn-1,4-Diamination of Naphthalene (5) and Benzene (6)^a

^aStandard reaction conditions for naphthalene (5): MTAD (1, 0.5 mmol, 1.0 equiv), naphthalene (5, 1.0 mmol, 2.0 equiv), EtOAc (0.1 M), visible light, −50 °C, 12 h; then addition of amine (1.0 mmol, 2.0 equiv) and [Pd] catalyst in THF, −20 °C, 20 h. Reaction conditions for benzene (6): MTAD (1, 1.0 mmol, 1.0 equiv), benzene (6, 10 mmol, 10 equiv), CH₂Cl₂ (0.2 M), visible light, −78 °C, 12 h; then addition of amine (2.0 mmol, 2.0 equiv) and [Pd] catalyst in THF, −20 °C, 20 h. Reported yields are of isolated products.