Efficient Ru-Catalyzed Electrochemical Homo- and Heterocoupling Reaction of Terminal Alkynes: Synthesis, In Vitro Anticancer Activity, and Docking Study
Kashyap J. Tamuli,
Bardwi Narzary,
Surovi Saikia
et al.
Abstract:With the objective
to identify novel anticancer leads, herein ruthenium-catalyzed
electrochemical homo- and heterocoupling reactions of terminal alkynes
have been developed for the synthesis of the desired products. Among
the synthesized 1,3-diynes, some of them were rigorously examined
for possible
in vitro
anticancer activity against
HeLa (human cervical cancer) and L6 normal (rat skeletal muscle) cell
lines. Additionally, the docking study was also performed toward 16
ovarian cancer t… Show more
Herein, we disclose the oxidative homocoupling of terminal alkynes under electrochemically generated cuprous catalysis. The scope of this protocol was established by preparing an array of structurally and electronically different 1,3-butadiyne derivatives. Good synthetic yields, functional group tolerance, oxidant-free conditions, and no cross-selectivity are some of the intrinsic advantages of this methodology. The developed chemistry features the electro-redox formation of copper acetylide, an intermediate appropriate for the Csp–Csp coupling step. The chemical state of copper in the acetylide intermediate was found to be Cu(I), as confirmed by click trapping experiments, cyclic voltammetry, EPR spectroscopy, and XPS. A competition reaction to determine the reactivity of electronically dissimilar acetylenes revealed that the product ratio is rather dependent on the electronic nature of the alkynyl substituents. To highlight the synthetic value of the products, selected diynes were subjected to chemical diversification.
Herein, we disclose the oxidative homocoupling of terminal alkynes under electrochemically generated cuprous catalysis. The scope of this protocol was established by preparing an array of structurally and electronically different 1,3-butadiyne derivatives. Good synthetic yields, functional group tolerance, oxidant-free conditions, and no cross-selectivity are some of the intrinsic advantages of this methodology. The developed chemistry features the electro-redox formation of copper acetylide, an intermediate appropriate for the Csp–Csp coupling step. The chemical state of copper in the acetylide intermediate was found to be Cu(I), as confirmed by click trapping experiments, cyclic voltammetry, EPR spectroscopy, and XPS. A competition reaction to determine the reactivity of electronically dissimilar acetylenes revealed that the product ratio is rather dependent on the electronic nature of the alkynyl substituents. To highlight the synthetic value of the products, selected diynes were subjected to chemical diversification.
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