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

Autor:	Vladimir V. Kouznetsov, Carlos E. Puerto Galvis, Marlyn C. Ortiz Villamizar
Rok vydání:	2020
Předmět:	chemistry.chemical_classification Organic Chemistry chemistry.chemical_element Alkyne Combinatorial chemistry Redox Catalysis A3 coupling reaction Transition metal chemistry Photocatalysis Iridium Visible spectrum
Zdroj:	Synthesis. 53:547-556
ISSN:	1437-210X 0039-7881
DOI:	10.1055/s-0040-1707370
Popis:	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.
Databáze:	OpenAIRE
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