Investigation of ortho-substituted aryl bromides as aromatic substrates in Pd-catalyzed synthesis of modified nucleosides

CHED 417

Felix Ngassa, ngassaf@gvsu.edu and Kyle DeKorver, ngassaf@gvsu.edu. Department of Chemistry, Grand Valley State University, 1 Campus Drive, Allendale, MI 49401
A palladium-catalyzed coupling of protected 2'-deoxyadenosine has been developed using simple and extended bromo-aromatic substrates, which include bromobenzene, o-bromoanisole, 1-bromo-2-nitrobenzene, 1-bromonaphthalene, 2-bromonaphthalene, 1-bromo-2-methoxynaphthalene, and 2,4,6-tri-t-butyl-bromobenzene. Optimum conditions were obtained using Pd2(dba)3, Xantphos, and Cs2CO3 as the palladium species, ligand, and base, respectively.