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. 2022 Mar 22;144(16):7072–7079. doi: 10.1021/jacs.2c01735

Scheme 4. Indole Dearomatization and Synthetic Applications.

Scheme 4

5 (0.1 mmol), 2a (0.4 mmol), NHC A (20 mol %), 4-CzlPN (5 mol %), K2HPO4 (2.0 equiv), and CH3CN/DMF (1 mL/0.1 mL) under irradiation with 2 × 45 W blue LEDs for 24 h.

1j (1.0 mmol), 2a (4.0 mmol), NHC A (20 mol %), Ir–F (2 mol %), K2HPO4 (2.0 equiv), and CH3CN/DMF (10.0 mL/1.0 mL) under irradiation with 2 × 45 W blue LEDs for 24 h.

Hydroxylamine hydrochloride (5.0 equiv), NaOAc (10.0 equiv), EtOH, 70 °C; p-TsOH (4.0 equiv), Toluene, 70 °C.

NaBH4 (2.0 equiv), MeOH/THF (1:1), 0 °C.