Synthetic Study on the Redox-Neutral C1-Alkynylation of Tetrahydroisoquinolines

The A3 Redox-Neutral C1-Alkynylation of Tetrahydroisoquinolines: A Comparative Study between Visible Light Photocatalysis and Transition-Metal Catalysis: M. C. Ortiz Villamizar, C. E. Puerto Galvis, V. V. Kouznetsov

Synthesis 2020, 52, DOI: 10.1055/s-0040-1707370


The three-component coupling of an amine, an aldehyde and an alkyne is commonly known as the A3 reaction. This process represents an efficient and versatile synthetic entry to propargylic amines, including tetrahydroisoquinolines (THIQs), which are pharmaceutically important scaffolds. Recently, the group of Professor Vladimir V. Kouznetsov from the Industrial University of Santander (Colombia) reported a detailed study on the redox-neutral options for applying the A3 reaction to THIQs synthesis, comparing visible light photocatalysis to transition-metal catalysis.

Professor Kouznetsov said: “We described a rapid and robust Cu(I)-based methodology for the synthesis of a series of 1-alkynylated THIQs after having studied the A3 redox-neutral C1‐alkynylation of THIQs under visible light photocatalysis and transition-metal approaches. This approach would help in the synthesis of bioactive THIQs containing promising pharmacophoric moieties.”

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