Abstract
AbstractA 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.
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