A General Strategy for Aliphatic C-H Functionalization Enabled by Organic Photoredox Catalysis was written by Margrey, Kaila A.;Czaplyski, William L.;Nicewicz, David A.;Alexanian, Erik J.. And the article was included in Journal of the American Chemical Society in 2018.Synthetic Route of C10H22O The following contents are mentioned in the article:
Synthetic transformations that functionalize unactivated aliphatic C-H bonds in an intermol. fashion offer unique strategies for the synthesis and late-stage derivatization of complex mols. Herein we report a general approach to the intermol. functionalization of aliphatic C-H bonds using an acridinium photoredox catalyst and phosphate salt under blue LED irradiation This strategy encompasses a range of valuable C-H transformations, including the direct conversions of a C-H bond to C-N, C-F, C-Br, C-Cl, C-S, and C-C bonds, in all cases using the alkane substrate as the limiting reagent. Detailed mechanistic studies are consistent with the intermediacy of a putative oxygen-centered radical as the hydrogen atom-abstracting species in these processes. This study involved multiple reactions and reactants, such as 3,7-Dimethyloctan-1-ol (cas: 106-21-8Synthetic Route of C10H22O).
3,7-Dimethyloctan-1-ol (cas: 106-21-8) belongs to alcohols. The oxygen atom of the strongly polarized O―H bond of an alcohol pulls electron density away from the hydrogen atom. This polarized hydrogen, which bears a partial positive charge, can form a hydrogen bond with a pair of nonbonding electrons on another oxygen atom. Secondary alcohols are easily oxidized without breaking carbon-carbon bonds only as far as the ketone stage. No further oxidation is seen except under very stringent conditions.Synthetic Route of C10H22O
Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts