Copper-catalyzed atom transfer radical addition (ATRA) has shown to be an effective method for the synthesis of small functionalized molecules. The bifunctional alkyl halide initiator 1,2-bis(bromoisobutyryloxy)ethane (BBiBE) was used for the ATRA of various acrylates [methyl, propargyl, ethylene glycol methyl ether]and acrylonitrile (Scheme 1) . Initially mediated by UV light, the reactions were performed under N2 at ambient temperature in methanol (MeOH) and catalyzed by [CuII(Me6TREN)Br] [Br] or [CuII(TPMA)Br] [Br] (Me6TREN = Tris[2-(dimethylamino)ethyl]amine; TPMA= Tris(2-pyridylmethyl)amine). To optimize the synthesis of diadducts, catalyst studies have been performed to determine the ideal loading to provide desirable conversions and yields. Two variations of ATRA reactions were performed to identify a more facile path for future use, providing comparably low yields with methyl acrylate (32% vs 39%). This methodology can eventually be extended to other multifunctional initiators (Figure 1).

Synthesis of small functionalized molecules using copper-catalyzed Atom Transfer Radical Addition (ATRA)

253rd National Meeting (2017)

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