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Ortiz Villamizar, Marlyn C.; Puerto Galvis, Carlos E.; Kouznetsov, Vladimir V.
Synthesis (Athens, Greece), 02/2021, Volume: 53, Issue: 3Journal Article
Abstract Considering the current challenges of the A 3 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(PPh 3 ) 3 ) and silver (AgNO 3 ) 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.
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