Issue 12, 2021

Visible light promoted photoredox C(sp3)–H bond functionalization of tetrahydroisoquinolines in flow

Abstract

A merger of organocatalysis and visible light photoredox catalysis performed in flow allowed access to a wide range of functionalized N-aryl-substituted tetrahydroisoquinolines (THIQs) in a formal C–H oxidation/Mannich reaction. Strecker type functionalization and copper-catalyzed alkynylation of several N-aryl-substituted THIQs were also successfully performed in flow, giving valuable products with high efficiencies. The use of custom-made porous polymeric type microreactors proved to be crucial regarding the C–H oxidation step and overall reaction performance.

Graphical abstract: Visible light promoted photoredox C(sp3)–H bond functionalization of tetrahydroisoquinolines in flow

Supplementary files

Article information

Article type
Communication
Submitted
28 Dec 2020
Accepted
25 Feb 2021
First published
25 Feb 2021

Org. Biomol. Chem., 2021,19, 2668-2675

Visible light promoted photoredox C(sp3)–H bond functionalization of tetrahydroisoquinolines in flow

A. Filipović, Z. Džambaski, D. Vasiljević-Radović and B. P. Bondžić, Org. Biomol. Chem., 2021, 19, 2668 DOI: 10.1039/D0OB02582H

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