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Photocatalytic Aminoarylation of Styrenes
Oniya L Valencia1, Peter Q Burleson1, Karl A Scheidt1
1Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208, United States.
None:
Arylethylamines are privileged motifs in bioactive compounds and pharmaceuticals. Described here is a novel photocatalytic aminoarylation of styrenes to afford arylethylamines utilizing commercially available reagents. Aryl iodides undergo single-electron reduction to yield an aryl radical intermediate, enabling subsequent addition to styrenes. The resulting benzylic radical then undergoes oxidation to a carbocation and is trapped by a nucleophilic amine. Mechanistic studies, including Stern-Volmer fluorescence quenching studies and radical trapping experiments, support the proposed catalytic cycle.
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