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Synthesis 2021; 53(03): 547-556
DOI: 10.1055/s-0040-1707370
paper

The A3 Redox-Neutral C1-Alkynylation of Tetrahydroisoquinolines: A Comparative Study between Visible Light Photocatalysis and Transition-Metal Catalysis

Marlyn C. Ortiz Villamizar 
,
Carlos E. Puerto Galvis 
,
Vladimir V. Kouznetsov  ∗
We thank the Departamento Administrativo de Ciencia, Tecnología e Innovación (Colombian Institute for Science and Research, COLCIENCIAS) under project no. 007-2017, cod. 110274558597 for financial support.
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Abstract

Considering the current challenges of the A3 redox-neutral C1-alkynylation of tetrahydroisoquinolines (THIQs), we studied this synthetic tool under visible light photocatalysis and transition-metal catalysis in order to describe alternative reaction conditions and discuss possible improvements to this process. We demonstrated that 1-alkynylated THIQs can be readily obtained by three different approaches: iridium-based photocatalysis and copper ([CuBr(PPh3)3]) and silver (AgNO3) catalysis under mild, selective and accessible reaction conditions. Among these approaches, the copper(I)-based methodology resulted in the most robust, optimal reaction conditions for the synthesis of a series of 18 1-alkynylated THIQs in moderate to excellent yields and with high selectivity for the endo-alkynylated products. Moreover, this reaction can be accelerated by microwave irradiation (120 °C, 15 min) affording a novel library of diverse THIQs with alkyne and N-substituent moieties, from unreactive and uncommon substrates, that could be further transformed into new compounds of interest.

Key words

A3 coupling reaction - C1-alkynylation - tetrahydroisoquinolines - photocatalysis - transition-metal catalysis

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1707370.
  • Supporting Information


Publication History

Received: 02 June 2020

Accepted after revision: 03 August 2020

Article published online:
21 September 2020

© 2020. Thieme. All rights reserved

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