Indole → N-(4-methylphenyl)indole

Participants

Reaction Conditions

Reaction Steps

An oven-dried test tube was purged with argon and then charged with 2-dicyclohexylphosphino-2′-methoxy-1,1′-biphenyl (14.5 mg, 0.038 mmol, 7.5 mol %) and Pd2(dba)3 (11.6 mg, 0.013 mmol, 5.0 mol % Pd). Toluene (1.0 mL), indole (71 mg, 0.61 mmol), 4-chlorotoluene (60 mL, 0.51 mmol), and NaOt-Bu (70 mg, 0.73 mmol) were then added. The tube was fitted with a septum, purged with argon and heated at 100° C. for 28 h. The reaction was then cooled to room temperature, diluted with ether (20 mL), filtered through Celite and concentrated in vacuo. The residue was purified by flash chromatography on silica gel to afford 99 mg (94%) of a colorless oil.

Provenance & Evidence