In 2018,Yan, Xiao-Biao; Li, Chun-Ling; Jin, Wen-Jie; Guo, Peng; Shu, Xing-Zhong published 《Reductive coupling of benzyl oxalates with highly functionalized alkyl bromides by nickel catalysis》.Chemical Science published the findings.Reference of 4-Bromotetrahydropyran The information in the text is summarized as follows:
Coupling reactions involving non-sulfonated C-O electrophiles provide a promising method for forming C-C bonds, but the incorporation of functionalized or secondary alkyl groups remains a challenge due to the requirement for well-defined alkylmetal species. In this study, a reductive nickel-catalyzed cross-coupling of benzyl oxalates with alkyl bromides, using oxalate as a new leaving group is reported. A broad range of highly functionalized alkyl units (such as functional groups: alkyl chloride, alc., aldehyde, amine, amide, boronate ester, ether, ester, heterocycle, phosphonate, strained ring) were efficiently incorporated at the benzylic position. The utility of this synthetic method was further demonstrated by late-stage modification of complex bioactive compounds Preliminary mechanistic experiments revealed that a radical process might be involved in the reaction. The results came from multiple reactions, including the reaction of 4-Bromotetrahydropyran(cas: 25637-16-5Reference of 4-Bromotetrahydropyran)
4-Bromotetrahydropyran(cas: 25637-16-5) is often used as reactant for: preparation of anthranilic acids as antibacterial agents with human serum albumin binding affinity; preparation of antiatherogenic antioxidant di-tert-butyldihydrobenzofuranols via Grignard reactions with di-tert-butyl(hydroxy)benzaldehyde derivatives; synthesis of gephyrotoxin via the Schmidt reaction.Reference of 4-Bromotetrahydropyran
Referemce:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics