Over the past few decades, harnessing of one-electron reactivity from visible light catalysis has emerged as an appealing tool to access radical intermediates, enabling C-C and C-X bond formations. In continuation of our interest in the N-O bond-mediated oxidative transformations, we introduce herein enoxybenzotriazoles as substrates for the photo-catalyzed radical Mannich type reaction of tertiary amines. We envisioned that the N-centered radical cation generated by single electron transfer would be deprotonated to produce an α-amino radical. The C(sp3)-H bond functionalized amine radical would react with the N-enoxybenzotriazole substrate furnishing β-amino ketone product and benzotriazole radical. Oxidation of IrII by benzotriazole radical would regenerate IrIII and complete the catalyst cycle.

Visible light-enabled radical Mannich reaction via sp3 C-H bond functionalization of tertiary amines

ACS Spring Meeting 2021

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