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Copper‐Catalyzed Cross‐Coupling Reactions of Nucleobases with Arylboronic Acids: An Efficient Access to N ‐Arylnucleobases
Author(s) -
Yue Yang,
Zheng ZhangGuo,
Wu Bo,
Xia ChuanQin,
Yu XiaoQi
Publication year - 2005
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200500589
Subject(s) - chemistry , nucleobase , phenylboronic acid , catalysis , copper , methanol , coupling (piping) , solvent , combinatorial chemistry , coupling reaction , organic chemistry , medicinal chemistry , dna , mechanical engineering , biochemistry , engineering
An efficient avenue for the direct N ‐arylation of nucleobases with arylboronic acids that is catalyzed by simple copper salts was discovered. The N ‐arylnucleobases were obtained in excellent yields at room temperature within 45 min when methanol and water were used as a mixed solvent. Under these conditions, the coupling reaction tolerates both electron‐donating and electron‐withdrawing substituents at the o ‐, m ‐, or p ‐positions of phenylboronic acid and gives the corresponding coupling products in moderate to excellent yields. Experimental results show that this route is the most efficient, facile, and mild method for the synthesis of N ‐arylnucleobases. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)