Photoelectron-transfer-catalyzed intermolecular carbon-carbon bond formation of primary, secondary, and tertiary amines with a,jS-unsaturated esters and nitriles using photosensitizers such as anthraquinone, acridone; and dicyanoanthracene has been investigated. The addition of a-aminoalkyl radicals, generated via photoelectron-transfer processes, to olefmic substrates and the subsequent 1,5-hydrogen abstraction reactions of the amine-olefin adduct radicals lead to a number of interesting multiple-olefin-added products. The adducts of the primary and secondary amines with ,ßunsaturated esters undergo further cyclizations to give spiro and cyclic lactams, respectively.
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