N,N'-Bis(2-phenyl-1-naphthyl)-1,2-benzenediamine

• 3-Bromoquinoline [B1013]
• 1-Butanol [B0704]
• N,N'-Bis(2-phenyl-1-naphthyl)-1,2-benzenediamine [B6801]
• Copper(I) Iodide [C2163]
• Sodium tert-Butoxide [S0450]
• DMSO

3-Bromoquinoline (300 mg, 1.44 mmol), 1-butanol (160 µL, 1.73 mmol), N,N'-Bis(2-phenyl-1-naphthyl)-1,2-benzenediamine (74.0 mg, 144 µmol), copper(I) iodide (13.7 mg, 72.1 µmol) and sodium tert-butoxide (277 mg, 2.88 mmol) were dissolved in DMSO (2 mL) and stirred at room temperature for 1.5 hours. The reaction was quenched with water and the aqueous layer was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and filtered. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate:hexane = 0:100 - 5:95) to give 3-butoxyisoquinoline as a yellow oil (227 mg, 78% yield).

The reaction mixture was monitored by NMR.
The reaction was carried out under a nitrogen atmosphere.

3-Butoxyisoquinoline

¹H NMR (270 MHz, CDCl₃); δ 8.65 (d, J = 3.0 Hz, 1H), 8.02 (dd, J = 6.8, 1.1 Hz, 1H), 7.70 (dd, J = 6.2, 1.9 Hz, 1H), 7.56-7.45 (m, 2H) 7.35 (d, J = 2.7 Hz, 1H), 4.07 (t, J = 6.5 Hz, 2H), 1.90-1.79 (m, 2H), 1.60-1.47 (m, 2H), 0.99 (t, J = 7.6 Hz, 3H).

• Activation of Aryl Chlorides for Suzuki Cross-Coupling by Ligandless, Heterogeneous Palladium
  • M. J. Strauss, M. E. Greaves, S. T. Kim, C. N. Teijaro, M. A. Schmidt, P. M. Scola, S. L. Buchwald, Angew. Chem. Int. Ed. 2024, 63, e202400333.

• Cu-Catalyzed Amination of Base-Sensitive Aryl Bromides and the Chemoselective N- and O-Arylation of Amino Alcohols
  • M. J. Strauss, K. X. Liu, M. E. Greaves, J. C. Dahl, S. T. Kim, Y. J. Wu, M. A. Schmidt, P. M. Scola, S. L. Buchwald, J. Am. Chem. Soc. 2024, 27, 18616.