By the addition of a reducing agent, catalyst regeneration in atom transfer radical addition (ATRA) and cyclization (ATRC) has significantly reduced the amount of catalyst, thus creating a �greener� process.  This method was first applied in the addition of polyhalogenated alkyl halides to various alkenes, and was extended to the utilization of monohalogenated substrates such as bromoacetonitrile (BrACN), 2-bromopropionitrile (BrPN), and 2-ethylbromophenylacetate (EBrP).  The single carbon-halogen bond formed from the monohalogenated alkyl halides is more expedient for further organic transformations.  After optimizing the reactions in NMR tubes, significantly higher yields were achieved when performed in pressure tubes with BrACN, BrPN, and EBrP, allowing increase in the reaction temperature regardless of the solvent.  Copper catalyzed ATRA reactions were generally much faster when conducted in pressure tubes .  The reactions were performed with BrACN, BrPN, and EBrP with alkenes such as 1-octene, styrene, methyl acrylate, and methyl methacrylate.

High pressure and temperature investigation of copper catalyzed atom transfer radical addition (ATRA) utilizing monohalogenated alkyl halides

248th National Meeting (2014)

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