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Hypervalent Iodine in Synthesis. Part 86
Author(s) -
Zhou Tao,
Li TiCong,
Chen ZhenChu
Publication year - 2005
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200590010
Subject(s) - chemistry , hypervalent molecule , uracil , selectivity , thymine , iodine , catalysis , copper , base (topology) , combinatorial chemistry , organic chemistry , biochemistry , mathematics , dna , mathematical analysis
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 copper‐catalyzed 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 ).