Copper-catalyzed atom transfer radical addition (ATRA) and [3+2] azide-alkyne cycloaddition (CuAAC) exhibit excellent potential in the synthesis of small functionalized molecules. Upon development of a one-pot approach, this methodology will eventually be extended to other multifunctional alkenes, which may have further implications regarding biomedical applications. Alkyne- and azide-terminated initiators were utilized in the ATRA reactions, which proceeded efficiently at ambient temperature using [Cu<sup>II</sup>(TPMA)Br][Br] catalyst in the presence of UV-light. The reaction of propargyl-2-bromoisobutyrate (PBiB) to ethylene glycol diacrylate (EGDA) afforded a relatively high yield of 73%. The desired adduct was isolated to perform a copper-catalyzed [3+2] azide-alkyne cycloaddition, generating corresponding 1,2,3-triazoles. Specifically, 3-azido-7-diethylamino coumarin was utilized as a click reagent, which displays fluorescent properties upon formation of the triazole linkage (Scheme 1).

Synthesis of small functionalized molecules using copper-catalyzed atom transfer radical addition (ATRA) and [3+2] azide-alkyne cycloaddition (CuAAC)

254th National Meeting (2017)

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