Hypervalent Iodine in Synthesis. Part 86 : Selective Copper-Catalyzed N-Monoarylation and N1,N3-Diarylation of Uracil and Its Derivatives with Diaryliodonium Salts

✍ Scribed by Tao Zhou; Ti-Cong Li; Zhen-Chu Chen

• Book ID: 102259192
• Publisher: John Wiley and Sons
• Year: 2005
• Tongue: German
• Weight: 86 KB
• Volume: 88
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.200590010

✦ Synopsis

N-Arylation of uracil and its derivatives 2 with diaryliodonium salts 1 was investigated in order to explore a new synthetic methodology associated with N-aryluracil derivatives. In the presence of K 2 CO 3 , the coppercatalyzed arylation gave N 1 ,N 3 -diarylation products with high selectivity and in good yields (Table 2). However, the use of NaOAc as the base in the copper-catalyzed arylation of 6-methyluracil (2a) resulted in N 3 -arylation products with high selectivity, and, in the copper-catalyzed arylation of uracil (2b) or 5-methyluracil ( thymine; 2c), N 1 -arylation products were the major products (Table 3).