Journal
TETRAHEDRON
Volume 65, Issue 21, Pages 4085-4091Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2009.03.064
Keywords
Alkynylation; Cross-coupling; Deoxyadenosine; Nucleosides; Sonogashira
Categories
Funding
- Grand Valley State University
- Chemistry Department at GVSU
- Weldon Fund
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The Sonogashira cross-coupling reaction offers a convenient route to C(sp)C(sp(2)) bond formation. Although the Sonogashira reaction has traditionally been carried out in the presence of Pd catalyst and a co-catalyst of Cu(I) salt, the use of Cu(I) salt is often not efficient because it leads to the formation of unwanted side-products. This has prompted interest in recent years in the development of Cu-free Sonogashira cross-coupling reaction conditions. In addition, the development of Cu-free Sonogashira cross-coupling conditions for the alkynylation of nucleoside derivatives remains largely unexplored. Herein, we demonstrate that Cu- and amine-free Sonogashira-type cross-coupling lead to successful alkynylation of aryl bromides and heteroaryl bromides. For the first time, we have extended this method for the alkynylation of protected 2'-deoxyadenosine at the C-6 position. (C) 2009 Elsevier Ltd. All rights reserved.
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