Atom transfer radical addition (ATRA) is a fundamental and versatile organic process for C-C bond formation via addition of various alkyl halides across the double bond of an alkene catalyzed by copper complexes. Atom transfer radical cyclization (ATRC) is intramolecular ATRA with the alkene and alkyl halide on the same molecule. This reaction is important for the ability to form lactones, lactams and cyclic alkenes. The utilization of catalyst regeneration has dramatically decreased the amount of catalyst from to 5-30 mol% to 0.003 mol% with the aid of reducing agents such as 2,2′-azobis(2-methylpropionitrile) (AIBN) and ascorbic acid. Using these techniques, novel copper complexes, including [Cu(DPzPA)X][X] (DPzPA=3,5-dimethylpyrazolylbis(2-pyridylmethyl)amine) (X=Br,Cl) and substituted ligands similar to this have been successfully employed for the ATRA and ATRC of alkyl halides such as CBr<sub>4</sub> and CCl<sub>4</sub> across various alkenes (1-octene, acrylonitrile, methyl acrylate, methyl methacrylate) in the presence of ascorbic acid as the reducing agent and various bromoacetamides and bromoacetates will be investigated for ATRC activity.

Utilization of pyrazole based copper complexes in atom transfer radical addition (ATRA) and atom transfer radical cyclization (ATRC)

249th National Meeting (2015)

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