Catalytic Ligand for Ullmann-type Coupling Using N,N'-Bis(2-phenyl-1-naphthyl)-1,2-benzenediamine

N,N'-Bis(2-phenyl-1-naphthyl)-1,2-benzenediamine [B6801] is a catalytic ligand used in Ullmann-type coupling reactions. In a TCI practical example, this ligand was used together with Copper(I) Iodide [C2163] to couple 3-bromoquinoline [B1013] with 1-butanol [B0704], using Sodium tert-Butoxide [S0450] as the base and DMSO as the solvent. The main advantage of this system is that the reaction proceeds at room temperature. In the experiment, 3-bromoquinoline (300 mg, 1.44 mmol) and 1-butanol (160 µL, 1.73 mmol) were stirred for 1.5 hours at room temperature under a nitrogen atmosphere. After purification by silica gel column chromatography, 3-butoxyquinoline was obtained as a yellow oil. The reaction was monitored by NMR.

Related products

• TCI B1013 5332-24-1 3-Bromoquinoline
• TCI B0704 71-36-3 1-Butanol
• TCI B6801 3035177-77-3 N,N'-Bis(2-phenyl-1-naphthyl)-1,2-benzenediamine
• TCI C2163 7681-65-4 Copper(I) Iodide

References

1. 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. << Prev Next >> Page Top

Source

• TCI Practical Example: www.tcichemicals.com/ID/en/product/tci-topics/TCIPracticalExample_20250526
• TCI product page B1013: tcichemicals.com/ID/en/p/B1013

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