In 2022,Planas, Oriol; Peciukenas, Vytautas; Leutzsch, Markus; Noethling, Nils; Pantazis, Dimitrios A.; Cornella, Josep published an article in Journal of the American Chemical Society. The title of the article was 《Mechanism of the Aryl-F Bond-Forming Step from Bi(V) Fluorides》.Safety of 4-Fluorobenzonitrile The author mentioned the following in the article:
The authors describe a combined exptl. and theor. mechanistic study of the C(sp2)-F bond formation from neutral and cationic high-valent organobismuth(V) fluorides, featuring a dianionic bis-aryl sulfoximine ligand. An exhaustive assessment of the substitution pattern in the ligand, the sulfoximine, and the reactive aryl on neutral triarylbismuth(V) difluorides revealed that formation of dimeric structures in solution promotes facile Ar-F bond formation. Noteworthy, theor. modeling of reductive elimination from neutral Bi(V) difluorides agrees with the exptl. determined kinetic and thermodn. parameters. Also, the addition of external fluoride sources leads to inactive octahedral anionic Bi(V) trifluoride salts, which decelerate reductive elimination. However, a parallel anal. for cationic bismuthonium fluorides revealed the crucial role of tetrafluoroborate anion as fluoride source. Both exptl. and theor. analyses conclude that C-F bond formation occurs through a low-energy five-membered transition-state pathway, where the F anion is delivered to a C(sp2) center, from a BF4 anion, reminiscent of the Balz-Schiemann reaction. The knowledge gathered throughout the study permitted a rational assessment of the key parameters of several ligands, identifying the simple sulfone-based ligand family as an improved system for the stoichiometric and catalytic fluorination of arylboronic acid derivatives In the experiment, the researchers used 4-Fluorobenzonitrile(cas: 1194-02-1Safety of 4-Fluorobenzonitrile)
4-Fluorobenzonitrile(cas: 1194-02-1) is used in the synthesis of flurenones, pharmaceutical prerequisites, as well as opiod receptor antagonists.Safety of 4-Fluorobenzonitrile
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts