Reductive coupling of benzyl oxalates with highly functionalized alkyl bromides by nickel catalysis was written by Yan, Xiao-Biao;Li, Chun-Ling;Jin, Wen-Jie;Guo, Peng;Shu, Xing-Zhong. And the article was included in Chemical Science in 2018.Application In Synthesis of 1-Bromo-4-methoxybutane This article mentions the following:
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. In the experiment, the researchers used many compounds, for example, 1-Bromo-4-methoxybutane (cas: 4457-67-4Application In Synthesis of 1-Bromo-4-methoxybutane).
1-Bromo-4-methoxybutane (cas: 4457-67-4) belongs to organobromine compounds. Many of the organo bromine compounds are relatively nonpolar. Bromine is more electronegative than carbon (2.8 vs 2.5) and hence the carbon in a carbon–bromine bond is electrophilic in nature. One prominent application of synthetic organobromine compounds is the use of polybrominated diphenyl ethers as fire-retardants, and in fact fire-retardant manufacture is currently the major industrial use of the element bromine.Application In Synthesis of 1-Bromo-4-methoxybutane
Referemce:
Bromide – Wikipedia,
bromide – Wiktionary