Table 2.

Arene scope of dearomative 1,4-hydroamination^a.

^aStandard reaction condition: MTAD (1, 0.5 mmol, 1.0 equiv.), arene [5.0 mmol (10 equiv.) for 7a−7h or 1.0 mmol (2.0 equiv.) for 7i−7m], CH₂CI₂ (0.1 M), visible light, −78 °C, 12 h; then solution of catalyst [Pd(dba)₂ (14.4 mg, 0.025 mmol, 5 mol%), ligand (0.050 mmol, 10 mol%), tetrahydrofuran (THF, 0.25 M)]; then K-Selectride^® (1.0 M solution in THF, 1.0 mL, 1.0 mmol, 2.0 equiv.). See experimental section for more details. Unless otherwise noted, reported yields are of isolated products, with ratio of constitutional isomers (in parentheses) determined by ¹H NMR of the crude reaction mixtures.

^bFor gram-scale reactions, L-Selectride^® (1.0 M solution in THF, 1.0 mL, 1.0 mmol, 2.0 equiv.) was used instead.

^cDue to product instability, reported yields were determined by ¹H NMR of reaction mixtures after workup using nitromethane as internal standard.

^dSPhos (20.5 mg, 0.050 mmol, 10 mol%) was used as ligand.

^eDavePhos (19.7 mg, 0.050 mmol, 10 mol%) was used as ligand.