Recommanded Product: [Ir(dtbbpy)(ppy)2]PF6. The reaction of aromatic heterocyclic molecules with protons is called protonation. Aromatic heterocycles are more basic than benzene due to the participation of heteroatoms. Compound: [Ir(dtbbpy)(ppy)2]PF6, is researched, Molecular C40H40F6IrN4P, CAS is 676525-77-2, about Alcohols as alkylating agents in heteroarene C-H functionalization. Author is Jin, Jian; MacMillan, David W. C..
Primary alcs., diols containing at least one primary alc. moiety, and tetrahydrofurans acted as alkylating agents for six-membered nitrogen heterocycles such as isoquinolines, quinolines, and pyridines in the presence of an iridium photocatalyst Ir(ppy)2(dtbbp)PF6 (ppy = 1,2′-phenylpyridinediyl; dtbpy = 4,4′-di-tert-butyl-2,2-bipyridine), a thiol such as α-mercaptopropanoic acid, and p-toluenesulfonic acid in DMSO under blue LED light to yield alkylated heterocycles such as 1-methylisoquinoline in 43-98% yields. The medicinal agents fasudil dihydrochloride and milrinone were methylated and 3-phenylpropylated, resp., using this method in 82% and 43% yields. The method avoids the use of thermal conditions or stoichiometric oxidants. The mechanism was studied using fluorescence quenching experiments; the key step in the process is proposed to be the spin-center shift of a hydroxyalkylheteroaryl radical to yield an alkylheteroaryl radical with loss of water, precedented in biol. and synthetic settings. In the absence of a thiol, the radical generated from 1-isoquinolinemethanol coupled with two alkenes and two 1-pyrrolecarboxylates to yield dihydrobenzoisoquinolines and pyrrolylmethylisoquinolines, resp., in 25-65% yields.
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Reference:
Copper catalysis in organic synthesis – NCBI,
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”