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Combining Bidentate Lewis Acid Catalysis and Photochemistry: Formal Insertion of o‑Xylene into an Enamine Double Bond

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journal contribution
posted on 12.05.2019, 00:00 authored by Sebastian Ahles, Julia Ruhl, Marcel A. Strauss, Hermann A. Wegner
A bidentate Lewis acid catalyzed domino inverse-electron-demand Diels–Alder reaction combined with a photoinduced ring opening formally inserts o-xylene moieties into enamine double bonds. After reduction, phenethylamines were obtained in good yields. The scope of the reaction was determined by variation of all three starting compounds: phthalazines, aldehydes, and amines.