Site-Selective C(sp3)-H Functionalization of Fluorinated Alkanes Driven by Polar Effects Using a Tungstate Photocatalyst was written by Fukuyama, Takahide;Nishikawa, Tomohiro;Ryu, Ilhyong. And the article was included in European Journal of Organic Chemistry in 2020.Name: 2,3,4,5,6-Perfluoropyridine The following contents are mentioned in the article:
The TBADT-catalyzed C(sp3)-H functionalization of perfluorophenyl- and perfluoroalkyl-substituted alkanes was studied to determine how the fluorous substituents affect site-selectivity. Alkylation of alkyl-substituted perfluorobenzene avoids ä¼?C-H bonds, unlike their alkylbenzene counterparts, allowing site-selective functionalization of C-H bonds remote to the aromatic ring. Alkylation of alkanes having a perfluoroalkyl group also avoided ä¼?C-H bonds. Radical polar effects in the SH2 transition states could explain this avoidance of ä¼?C-H functionalization. This study involved multiple reactions and reactants, such as 2,3,4,5,6-Perfluoropyridine (cas: 700-16-3Name: 2,3,4,5,6-Perfluoropyridine).
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 kJè·¯molé? in pyridine vs. 150 kJè·¯molé? in benzene). One of the examples of pyridines is the well-known alkaloid lithoprimidine, which is an A3 adenosine receptor antagonist and N,N-dimethylaminopyridine (DMAP) analog, commonly used in organic synthesis.Name: 2,3,4,5,6-Perfluoropyridine