Ton, Stephanie J.; Neumann, Karoline T.; Noerby, Peter; Skrydstrup, Troels published the artcile< Nickel-Mediated Alkoxycarbonylation for Complete Carbon Isotope Replacement>, SDS of cas: 112-63-0, the main research area is isotopically labeled aliphatic methyl carboxylate preparation; alkyl iodide alkoxycarbonylation nickel complete carbon isotope replacement.
In this paper, authors disclose a direct synthetic route allowing for full carbon isotope replacement via a nickel-mediated alkoxycarbonylation. Employing a nickel(II) pincer complex ([(N2N)Ni-Cl]) in combination with carbon-13 labeled CO, alkyl iodide, sodium methoxide, photocatalyst, and blue LED light, it was possible to generate the corresponding isotopically labeled aliphatic Me carboxylates in good yields. Furthermore, the developed methodol. was applied to the carbon isotope substitution of several pharmaceutically active compounds, whereby complete carbon-13 labeling was successfully accomplished. It was initially proposed that the carboxylation step would proceed via the in situ formation of a nickellacarboxylate, generated by CO insertion into the Ni-alkoxide bond. However, preliminary mechanistic investigations suggest an alternative pathway involving attack of an open shell species generated from the alkyl halide to a metal ligated CO to generate an acyl Ni(III) species. Subsequent reductive elimination involving the alkoxide eventually leads to carboxylate formation. An excess of the alkoxide was essential for obtaining a high yield of the product. In general, the presented methodol. provides a simple and convenient setup for the synthesis and carbon isotope labeling of aliphatic carboxylates, while providing new insights about the reactivity of the N2N nickel pincer complex applied.
Journal of the American Chemical Society published new progress about Aliphatic compounds Role: SPN (Synthetic Preparation), PREP (Preparation) (Me carboxylates). 112-63-0 belongs to class esters-buliding-blocks, and the molecular formula is C19H34O2, SDS of cas: 112-63-0.
Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics