The mediated electroreductive cyclization (ERC) reaction allows the substitution of an electrocatalyst as the stoichiometric source of electrons rather than the cathode, with the advantage of chemoselectivity through a more positive potential than necessary in the direct substrate reduction. Metal salens can play the role of electrocatalysts for mediated ERC reactions, provided that they operate within a specific potential window where electron transfer can take place. The mechanism of these reactions is unknown, but it has been postulated that inner sphere electron transfer is a likely pathway. A study of cyclic voltammetric properties of reduced nickel salen in the presence of an a,�-unsaturated carbonyl compound was employed to analyze the mechanism of nickel salen's catalytic behavior in ERC reactions. Bulk electrolysis was also employed, using methyl cinnamate, in an attempt to isolate a modified electrocatalyst and verify the inner sphere electron transfer mechanistic pathway.

Electroreductive cyclization of methyl cinnamate in the presence of nickel(II) salen: A mechanistic study

240th National Meeting (2010)

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