Herein, visible light mediated organophoto redox catalysed simple and convenient method for the α-benzylation and α-oxygenation of tertiary amines is demonstrated. Synthesis of novel thiophenol based donor acceptor organophotoredox catalysts 4 a-4 d were investigated along with commercial catalyst 4-CzIPN (4 e). A diverse biologically active α-benzylated tetrahydroisoquinolines and natural products such as (±)-Norlaudanosine, (±)-laudanosine and (±)-xylopinine have been synthesized under the optimized conditions in yields ranging from from 62-91%. Exploitation of synthesized α-benzylated compound using present phtoredox catalyzed conditions gave rise to dehydyrogenative benzylic oxidation product under oxygen atmosphere which is known to display biologically and structurally important properties. Also, various N-protected tertiary amines were found to be suitable for the α-oxygenation reactions using catalyst 4 e and resulted in good yields (61-85%).
Keywords: N-aryltetrahydroisoquinolines; Natural products; Visible light; organophoto redox catalysts; α-benzylation; α-oxygenation.
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