《Efficient C-H Amination Catalysis Using Nickel-Dipyrrin Complexes》 was published in Journal of the American Chemical Society in 2020. These research results belong to Dong, Yuyang; Clarke, Ryan M.; Porter, Gerard J.; Betley, Theodore A.. Related Products of 89466-08-0 The article mentions the following:
A dipyrrin-supported nickel catalyst (AdFL)Ni(py) (AdFL: 1,9-di(1-adamantyl)-5-perfluorophenyldipyrrin; py: pyridine) displays productive intramol. C-H bond amination to afford N-heterocyclic products using aliphatic azide substrates. The catalytic amination conditions are mild, requiring 0.1-2% catalyst loading and operational at room temperature The scope of C-H bond substrates was explored and benzylic, tertiary, secondary, and primary C-H bonds are successfully aminated. The amination chemoselectivity was examined using substrates featuring multiple activatable C-H bonds. Uniformly, the catalyst showcases high chemoselectivity favoring C-H bonds with lower bond dissociation energy as well as a wide range of functional group tolerance (e.g., ethers, halides, thioethers, esters, etc.). Sequential cyclization of substrates with ester groups could be achieved, providing facile preparation of indolizidine framework that is commonly found in a variety of alkaloids. The amination cyclization reaction mechanism was examined employing NMR spectroscopy to determine the reaction kinetic profile. A large, primary intermol. kinetic isotope effect (KIE = 31.9 ± 1.0) suggests H-atom abstraction (HAA) is the rate determining step, indicative of H-atom tunneling being operative. The reaction rate has first order dependence in the catalyst and zeroth order in substrate, consistent with the resting state of the catalyst as the corresponding nickel iminyl radical. The presence of the nickel iminyl was determined by multi-nuclear NMR spectroscopy observed during catalysis. The activation parameters (ΔH≠ = 13.4 ± 0.5 kcal/mol; ΔS≠ = -24.3 ± 1.7 cal/mol·K) were measured using Eyring anal., implying a highly ordered transition state during the HAA step. The proposed mechanism of rapid iminyl formation, rate-determining HAA, and subsequent radical recombination was corroborated by intramol. isotope labeling experiments and theor. calculations In addition to this study using 2-Hydroxyphenylboronic acid, there are many other studies that have used 2-Hydroxyphenylboronic acid(cas: 89466-08-0Related Products of 89466-08-0) was used in this study.
2-Hydroxyphenylboronic acid(cas: 89466-08-0) belongs to acyl phenylboronic acid. Phenylboronic acid (PBA) has been used to extract β-blockers (a class of aminoalcohol-containing drugs) from aqueous solution, rat, and human plasma. Related Products of 89466-08-0
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