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Communication | Special issue | Vol 66, No. 1, 2005, pp.51-56
Published online, 28th October, 2005
DOI: 10.3987/COM-05-S(K)13
■ Practical Halogenations of Nucleosides Using Tetrabutylammonium Peroxydisulfate

Vasu Sampath, Vidyadhar Jadhav, Hee Yoon Lee,* and Yong Hae Kim*

*Department of Chemistry, Center for Molecular Design and Synthesis, Korea Advanced Institute of Science and Technology, 373-1, Kusong-Dong, Yusung-Gu, Taejon 305-701,Korea

Abstract

Direct halogenation of a wide range of acetylated pyrimidine and purine nucleosides was achieved with high regioselectivity in good yields using tetrabutylammonium peroxydisulfate 1. Treatment of protected nucleosides with HCl/DMF or inorganic salts such as LiCl or NaCl in MeCN/AcOH in the presence of 1 gave the corresponding chlorinated nucleosides and bromination was achieved with N-bromosuccinimide in MeCN in the presence of 1.