Radical hydroxymethylation of alkyl iodides using formaldehyde as a C1 synthon.
AuthorsCaiger, Lewis; orcid: 0000-0001-5156-9684
Sinton, Conar; orcid: 0000-0002-5588-7548
Constantin, Timothée; orcid: 0000-0001-5376-1557
Douglas, James J
Sheikh, Nadeem S
Juliá, Fabio; orcid: 0000-0001-8903-4482
Leonori, Daniele; orcid: 0000-0002-7692-4504
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AbstractRadical 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.
CitationChemical science, volume 12, issue 31, page 10448-10454
DescriptionFrom Europe PMC via Jisc Publications Router
History: epub 2021-07-06, ppub 2021-08-01
Publication status: Published
Funder: European Research Council; Grant(s): 758427
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