Radical hydroxymethylation of alkyl iodides using formaldehyde as a C1 synthon.
Abstract
Radical hydroxymethylation using formaldehyde as a C1 synthon is challenging due to the reversible and endothermic nature of the addition process. Here we report a strategy that couples alkyl iodide building blocks with formaldehyde through the use of photocatalysis and a phosphine additive. Halogen-atom transfer (XAT) from α-aminoalkyl radicals is leveraged to convert the iodide into the corresponding open-shell species, while its following addition to formaldehyde is rendered irreversible by trapping the transient O-radical with PPh<sub>3</sub>. This event delivers a phosphoranyl radical that re-generates the alkyl radical and provides the hydroxymethylated product.Citation
Chemical science, volume 12, issue 31, page 10448-10454Type
articleDescription
From Europe PMC via Jisc Publications RouterHistory: epub 2021-07-06, ppub 2021-08-01
Publication status: Published
Funder: European Research Council; Grant(s): 758427
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