In 2022,Wang, Hui; Han, Wangyujing; Noble, Adam; Aggarwal, Varinder K. published an article in Angewandte Chemie, International Edition. The title of the article was 《Dual Nickel/Photoredox-Catalyzed Site-Selective Cross-Coupling of 1,2-Bis-Boronic Esters Enabled by 1,2-Boron Shifts》.Name: 2-Bromobenzonitrile The author mentioned the following in the article:
Site-selective transition-metal-catalyzed mono-deboronative cross-couplings of 1,2-bis-boronic esters are valuable methods for the synthesis of functionalized organoboron compounds However, such cross-couplings are limited to reaction of the sterically less hindered primary boronic ester. Herein, we report a nickel/photoredox-catalyzed mono-deboronative arylation of 1,2-bis-boronic esters that is selective for coupling of the more sterically hindered secondary/tertiary position. This is achieved by taking advantage of a 1,2-boron shift of primary β-boryl radicals to the thermodynamically favored secondary/tertiary radicals, which are subsequently intercepted by the nickel catalyst to enable arylation. The mild conditions are amenable to a broad range of aryl halides to give β-aryl boronic ester products in good yields and with high regioselectivity. This method also allows stereodivergent coupling of cyclic cis-1,2-bis-boronic esters to give trans-substituted products. The results came from multiple reactions, including the reaction of 2-Bromobenzonitrile(cas: 2042-37-7Name: 2-Bromobenzonitrile)
2-Bromobenzonitrile(cas: 2042-37-7) is used as a starting material to synthesize novel benzothiophene derivatives that were found to exhibit antibacterial and antifungal activity. It is commonly employed in reactions that require an electron-rich species to carry out nucleophilic substitution (or addition) reactions.Name: 2-Bromobenzonitrile
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts