Transition-Metal-Free Borylation of Alkyl Iodides via a Radical Mechanism was written by Liu, Qianyi;Hong, Junting;Sun, Beiqi;Bai, Guangcan;Li, Feng;Liu, Guoquan;Yang, Yang;Mo, Fanyang. And the article was included in Organic Letters in 2019.Reference of 4457-67-4 This article mentions the following:
The authors describe an operationally simple transition-metal-free borylation of alkyl iodides. This method uses com. available diboron reagents as the B source and exhibits excellent functional group compatibility. Also, a diverse range of primary and secondary alkyl iodides could be effectively transformed to the corresponding alkylboronates in excellent yield. Mechanistic studies suggest that this borylation reaction proceeds through a single-electron transfer mechanism featuring the generation of an alkyl radical intermediate. In the experiment, the researchers used many compounds, for example, 1-Bromo-4-methoxybutane (cas: 4457-67-4Reference of 4457-67-4).
1-Bromo-4-methoxybutane (cas: 4457-67-4) belongs to organobromine compounds. Bromine is more electronegative than carbon (2.9 vs 2.5). Consequently, the carbon in a carbon–bromine bond is electrophilic, i.e. alkyl bromides are alkylating agents. The reactivity of organobromine compounds resembles but is intermediate between the reactivity of organochlorine and organoiodine compounds. For many applications, organobromides represent a compromise of reactivity and cost.Reference of 4457-67-4
Referemce:
Bromide – Wikipedia,
bromide – Wiktionary