38580-68-6Relevant articles and documents
Radical hydroxymethylation of alkyl iodides using formaldehyde as a C1 synthon
Caiger, Lewis,Constantin, Timothée,Douglas, James J.,Juliá, Fabio,Leonori, Daniele,Sheikh, Nadeem S.,Sinton, Conar
, p. 10448 - 10454 (2021/08/20)
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 PPh3. This event delivers a phosphoranyl radical that re-generates the alkyl radical and provides the hydroxymethylated product.
Synthesis of epibatidine analogues having a 2-substituted 2-azabicyclo[2.2.2]octane skeleton
Wauters, Iris,De Blieck, Ann,Muylaert, Koen,Heugebaert, Thomas S. A.,Stevens, Christian V.
, p. 1296 - 1304 (2014/03/21)
The synthesis of 1-cyano-2-aza-[2.2.2]bicyclooctanes has been studied using the dynamic cyanide addition to cyclohexanone derivatives. These compounds were further elaborated into a new class of epibatidine derivatives from which a number of examples were
Control of transient aluminum-aminals for masking and unmasking reactive carbonyl groups
Barrios, Francis J.,Springer, Brannon C.,Colby, David A.
supporting information, p. 3082 - 3085 (2013/07/26)
A new reagent, the dimethylaluminum N,O-dimethylhydroxylamine complex, is effective at masking reactive carbonyl groups in situ from nucleophilic addition. This reagent allows chemoselective addition of reducing reagents, Grignard reagents, organolithiums, Wittig reagents, and enolates into substrates with multiple carbonyl groups. Moreover, the trapped carbonyl group, a stable aminal, can be unmasked in situ for additional synthetic manipulations.