By the addition of a reducing agent, catalyst regeneration in atom transfer radical addition (ATRA) and cyclization (ATRC) has significantly reduced the amount of transition metal 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 alkyl halides such as bromoacetonitrile (BrACN), 2-bromopropionitrile (BrPN), and 2-ethyl bromophenyl acetate (EBrP).  The single carbon-halogen bond formed from the monohalogenated alkyl halides is more expedient for further organic transformations.  Optimal conditions including solvents, temperatures, and amount of reducing agent for the reactions of the monohalogenated alkyl halides to alkenes such as 1-octene, styrene, methyl acrylate, and methyl methacrylate were found.

Monohalogenated alkyl halides utilized in transition metal catalyzed atom transfer radical addition (ATRA)

246th National Meeting (2013)

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