In 2022,Sharma, Brijesh M.; Nikam, Arun V.; Lahore, Santosh; Ahn, Gwang-Noh; Kim, Dong-Pyo published an article in Chemistry – A European Journal. The title of the article was 《Cyanide-Free Cyanation of sp2 and sp-Carbon Atoms by an Oxazole-Based Masked CN Source Using Flow Microreactors》.Name: 2-Bromobenzonitrile The author mentioned the following in the article:
This work reports a cyanide-free continuous-flow process for cyanation of sp2 and sp carbons to synthesize aryl, vinyl and acetylenic nitriles from (5-methyl-2-phenyloxazol-4-yl) boronic acid [OxBA] reagent as a sole source of carbon-bound masked -CN source. Non-toxic and stable OxBA reagent is generated by lithiation-borylation of bromo-oxazole, and the consecutive Suzuki-Miyaura cross-coupling with aryl, vinyl, or acetylenic halides and demasking [4+2]/retro-[4+2] sequence were successfully accomplished to give the desired cyano compounds with reasonably good yields in a four-step flow manner. A unique feature of this cyanation protocol in flow enables to cyanate a variety of sp2 and sp carbons to produce a broad spectrum of aryl acetonitrile. It is envisaged that the OxBA based cyanation would replace existing unstable and toxic approaches as well as non-toxic cyanation using two different sources of “”C”” and “”N”” to incorporate the -CN group. In the experiment, the researchers used many compounds, for example, 2-Bromobenzonitrile(cas: 2042-37-7Name: 2-Bromobenzonitrile)
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. This substrate molecule undergoes a palladium-catalyzed coupling reaction to form an aromatic ring. The light emission from this reaction can be seen in the reaction solution.Name: 2-Bromobenzonitrile
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts