Silicon-Carbon Bond Formation via Nickel-Catalyzed Cross-Coupling of Silicon Nucleophiles with Unactivated Secondary and Tertiary Alkyl Electrophiles was written by Chu, Crystal K.;Liang, Yufan;Fu, Gregory C.. And the article was included in Journal of the American Chemical Society in 2016.Reference of 57293-19-3 This article mentions the following:
A wide array of cross-coupling methods for the formation of C-C bonds from unactivated alkyl electrophiles were described in recent years. In contrast, progress in the development of methods for the construction of C-heteroatom bonds has lagged; for example, there were no reports of metal-catalyzed cross-couplings of unactivated secondary or tertiary alkyl halides with Si nucleophiles to form C-Si bonds. The authors address this challenge, establishing that a simple, com. available Ni catalyst (NiBr2璺痙iglyme) can achieve couplings of alkyl bromides with nucleophilic Si reagents under unusually mild conditions (e.g., -20鎺?; especially noteworthy is the authors’ ability to employ unactivated tertiary alkyl halides as electrophilic coupling partners, which is still relatively uncommon in the field of cross-coupling chem. Stereochem., relative reactivity, and radical-trap studies are consistent with a homolytic pathway for C-X bond cleavage. In the experiment, the researchers used many compounds, for example, 1-(3-Bromopropyl)-4-methoxybenzene (cas: 57293-19-3Reference of 57293-19-3).
1-(3-Bromopropyl)-4-methoxybenzene (cas: 57293-19-3) belongs to organobromine compounds. Bromine is more electronegative than carbon (2.9 vs 2.5). Consequently, the carbon in a carbon閳ユ彽romine bond is electrophilic, i.e. alkyl bromides are alkylating agents. 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.Reference of 57293-19-3
Referemce:
Bromide – Wikipedia,
bromide – Wiktionary