The author of 《Nickel-Catalyzed Hydrophosphonylation and Hydrogenation of Aromatic Nitriles Assisted by Lewis Acid》 were Islas, Rosa E.; Garcia, Juventino J.. And the article was published in ChemCatChem in 2019. Reference of 4-Fluorobenzonitrile The author mentioned the following in the article:
In this paper, we describe the catalytic hydrophosphonylation of several aromatic nitriles used to synthesize α-aminophosphonates (α-APs) using com. available trialkyl phosphites (P(OR)3, R=Et, iPr, Bu,) and simple and inexpensive nickel chloride (NiCl2.6H2O) as the catalytic precursor. The use of triethylborane (Et3B) as a Lewis acid (LA) was mandatory in order to successfully perform H-phosphite moiety incorporation at the CN bond of non-activated benzonitriles (BN) derivatives Interestingly, when a highly activated BN such as 2,3,4,5,6-pentafluorobenzonitrile (BN-g) was employed, it was possible to perform the reaction in the absence of an LA using milder reaction conditions. Also, we found that using HP(O)(OiPr)2 as a starting material afforded the aminobisphosphonate derivative with better selectivity than using the method involving P(OiPr)3 as the initial reagent. Remarkably, when using HP(O)(OiPr)2 with an excess of Et3B, the reaction’s selectivity completely changed to yield N-benzyl- benzylimine (BBI) and 2,4,5-triphenylimidazole. In the part of experimental materials, we found many familiar compounds, such as 4-Fluorobenzonitrile(cas: 1194-02-1Reference of 4-Fluorobenzonitrile)
4-Fluorobenzonitrile(cas: 1194-02-1) is used as chemical intermediate, solvent for perfumes and pharmaceuticals, stabilizer for chlorinated solvents, HPLC analysis, catalyst and component of transition-metal complex catalysts.Reference of 4-Fluorobenzonitrile
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts