Au(I) Catalyzed HF Transfer: Tandem Alkyne Hydrofluorination and Perfluoroarene Functionalization was written by Mulryan, Daniel;Rodwell, Jack;Phillips, Nicholas A.;Crimmin, Mark R.. And the article was included in ACS Catalysis in 2022.Reference of 700-16-3 The following contents are mentioned in the article:
Herein, a catalytic protocol in which an equivalent of HF was generated from a perfluoroarene|nucleophile pair and transferred directly to an alkyne was reported. The reaction was catalyzed by [Au(IPr)NiPr2] (IPr = N,N’-1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene). HF transfer generated two useful products in the form of functionalized fluoroarenes and fluoroalkenes. Mechanistic studies (rate laws, KIEs, d. functional theory (DFT) calculations, competition experiments) were consistent with the Au(I) catalyst facilitating a catalytic network involving both concerted SNAr and hydrofluorination steps. The nature of the nucleophile impacted the turnover-limiting step. This study involved multiple reactions and reactants, such as 2,3,4,5,6-Perfluoropyridine (cas: 700-16-3Reference of 700-16-3).
2,3,4,5,6-Perfluoropyridine (cas: 700-16-3) belongs to pyridine derivatives. Pyridine has a dipole moment and a weaker resonant stabilization than benzene (resonance energy 117 kJ路mol鈭? in pyridine vs. 150 kJ路mol鈭? in benzene). Pyridine derivatives are also useful as small-molecule 伪-helix mimetics that inhibit protein-protein interactions, as well as functionally selective GABA ligands.Reference of 700-16-3