The author of 《Nickel/Cobalt-Catalyzed C(sp3)-C(sp3) Cross-Coupling of Alkyl Halides with Alkyl Tosylates》 were Komeyama, Kimihiro; Michiyuki, Takuya; Osaka, Itaru. And the article was published in ACS Catalysis in 2019. Synthetic Route of C5H9BrO The author mentioned the following in the article:
The C(sp3)-C(sp3) cross-coupling of alkyl halides with alkyl tosylates has been developed by employing a combination of nickel and nucleophilic cobalt catalysts in the presence of a manganese reductant. This method provides a straightforward route to a diverse set of not only secondary-primary but also primary-primary C(sp3)-C(sp3) linkages under mild conditions without using alkyl-metallic reagents. Mechanistic studies suggest the formation of alkyl radicals from both alkyl halides and alkyl tosylates. Addnl., cross-coupling could be applied to the short-step synthesis of a histone deacetylase inhibitor, Vorinostat. In the experiment, the researchers used many compounds, for example, 4-Bromotetrahydropyran(cas: 25637-16-5Synthetic Route of C5H9BrO)
4-Bromotetrahydropyran(cas: 25637-16-5) is often used as reactant for: nickel-catalyzed alkyl-alkyl Suzuki coupling reactions with boron reagents, preparation of a selective small-molecule melanocortin-4 receptor agonist with efficacy in a pilot study of sexual dysfunction in humans; preparation of aliphatic hydrocarbons via nickel-catalyzed Suzuki cross-coupling with alkylboranes.Synthetic Route of C5H9BrO
Referemce:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics