Xu, Qing-Hao; Wei, Li-Pu; Xiao, Bin published an article in 2022. The article was titled 《Alkyl-GeMe3: Neutral Metalloid Radical Precursors upon Visible-Light Photocatalysis》, and you may find the article in Angewandte Chemie, International Edition.Electric Literature of C7H4BrN The information in the text is summarized as follows:
Single-electron transfer (SET) oxidation of ionic hypervalent complexes, in particular alkyltrifluoroborates (Alkyl-BF3-) and alkylbis(catecholato)silicates (Alkyl-Si(cat)2-), have contributed substantially to alkyl radical generation compared to alkali or alk. earth organometallics because of their excellent activity-stability balance. Herein, another proposal is reported by using neutral metalloid compounds, Alkyl-GeMe3, as radical precursors. Alkyl-GeMe3 shows comparable activity to that of Alkyl-BF3- and Alkyl-Si(cat)2- in radical addition reactions. Moreover, Alkyl-GeMe3 is the first successful group 14 tetraalkyl nucleophile in nickel-catalyzed cross-coupling. Meanwhile, the neutral nature of these organogermanes offset the limitation of ionic precursors in purification and derivatization. A preliminary mechanism study suggests that an alkyl radical is generated from a tetraalkylgermane radical cation with the assistance of a nucleophile, which may also result in the development of more non-ionic alkyl radical precursors with a metalloid center. In the experimental materials used by the author, we found 2-Bromobenzonitrile(cas: 2042-37-7Electric Literature of C7H4BrN)
2-Bromobenzonitrile(cas: 2042-37-7) is a precursor to the quinazolinones, a class of drugs used to treat autoimmune diseases and coronary heart disease. In addition, 2-bromobenzonitrile can be used for the Suzuki coupling reaction.Electric Literature of C7H4BrN
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts