15445-66-6Relevant academic research and scientific papers
Phenazine-Based Donor Acceptor Systems as Organic Photocatalysts for "metal-free" C-N/C-C Cross-Coupling
Deol, Harnimarta,Singh, Gurpreet,Kumar, Manoj,Bhalla, Vandana
, p. 11080 - 11093 (2020/10/12)
With an aim to achieve a balance between ground-state and excited-state reduction potential of donor acceptor systems for efficient C-N/C-C cross-coupling, a series of donor acceptor systems DA1-DA4 have been synthesized by varying the donor strength and connecting positions. With an increase in donor strength, systematic elevation in the ground-state reduction potential and decrease in the HOMO-LUMO gap was observed. Interestingly, all the derivatives DA1-DA4 could catalyze the C-N bond formation reaction between activated aryl halides and amines at low catalytic loading under metal-free conditions without the need of any external base upon irradiation with white LED. A balance was realized in the case of derivative DA2, which exhibits high efficiency in C-N couplings. Different control experiments support the validity of the energy as well as electron transfer pathways in the visible light-mediated C-N bond formation. This study further reveals the potential of derivative DA1 in "metal-free"Sonogashira coupling involving activated aryl halides which is attributed to its high excited-state reduction potential.
Magnesium-mediated arylation of amines via C-F bond activation of fluoroarenes
Bole, Leonie J.,Davin, Laia,Kennedy, Alan R.,McLellan, Ross,Hevia, Eva
supporting information, p. 4339 - 4342 (2019/04/26)
A series of new Mg(ii) amides featuring a bulky β-diketiminate backstop ligand, has been synthesised. These complexes are demonstrated to be excellent sources of nucleophilic amides that can participate in rapid C-F activation of several fluoroarenes at room temperature or using microwave assistance, leading to the installment of synthetically important C-N bonds via nucleophilic substitution.
Quantitative estimation of the reactivity of perfluorinated methylbenzenes and benzocycloalkenes in nucleophilic substitution reactions
Rodionov, Peter P.,Osina, Ol'Ga I.,Platonov, Vyacheslav E.,Yakobson, Georg G.
, p. 986 - 993 (2007/10/02)
The kinetics of the reactions of perfluorinated xylenes, mesitylene, p-cymene, benzocycloalkenes (benzocyclobutene, indane, tetralin) and octafluoronaphthalene with sodium methoxide and piperidine have been studied.Rate constants of the reactions of perfluorinated aromatic compounds with sodium methoxide (taking into account one reaction centre) are shown to incease in the order: hexafluorobenzene perfluoro-p-xylene ca.= perfluoro-p-cymene octafluorotoluene ca.= perfluoro-m-xylene perfluoromesitylene ca.= perfluoro-o-xylene.In the reactions with piperidine, a different sequence was observed: hexafluorobenzene perfluoro-p-xylene perfluoro-p-cymene perfluoromesitylene perfluoro-m-xylene octafluorotoluene perfluoro-o-xylene.In the reactions of perfluorobenzocycloalkenes with sodium methoxide and piperidine, the reactivity grows by about a factor of 2 with increase of the perfluoroalicyclic ring size by one CF2-group, in the following order: perfluorobenzocyclobutene perfluoroindan perfluorotetralin.
