1111073-25-6Relevant articles and documents
Simple methodology for heck arylation at C-8 of adenine nucleosides
Lagisetty, Pallavi,Zhang, Li,Lakshmana, Mahesh K.
supporting information; experimental part, p. 602 - 608 (2009/04/11)
A simple method for the arylation of 8-vinyladenine nucleoside derivatives is reported. With a broad set of aryl iodides and bromides, the reaction is catalyzed by the simple combination palladium acetate/tris(o-tolyl)phosphine/ triethylamine [Pd-(OAc)2/(o-tol)3P/Et3N]. As expected, aryl chlorides are more difficult coupling partners but some undergo reactions with more exotic catalysts. Although trans-olefins are the major products, minor amounts of cis-isomers are detected in some cases, and a post-arylation mechanism for their formation is proposed. Finally, by subtle catalyst modulation chemoselective N-arylation of the nucleoside can be achieved in the presence of the vinyl moiety.