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Hypervalent iodine in synthesis: Part 86. Selective copper-catalyzed N-monoarylation and N1,N3-diarylation of uracil and its derivatives with diaiyliodonium salts
Zhou, Tao,Li, Ti-Cong,Chen, Zhen-Chu
, p. 290 - 296 (2007/10/03)
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 K2CO3, the copper-catalyzed arylation gave N1,N3-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 N3-arylation products with high selectivity, and, in the copper-catalyzed arylation of uracil (2b) or 5-methyluracil (=thymine; 2c), N1-arylation products were the major products (Table 3).
