7402-91-7Relevant academic research and scientific papers
Domino C–H Activation Reactions through Proximity Effects
Lotz, Florian,Kahle, Klaus,Kangani, Mehrnoush,Senthilkumar, Soundararasu,Tietze, Lutz F.
, p. 5562 - 5569 (2018/10/20)
Proximity effects permit C–H activation reactions without directing groups. Here competitive reactions of selected substrates were investigated which allow a domino-carbopalladation/Mizoroki–Heck reaction and a domino-carbopalladation/C–H activation reaction. In the Pd-catalyzed transformation of the enantio- and diastereopure alkyne 8a the tetra-substituted alkenes 10 and 11 were formed almost exclusively through a domino carbopalladation/Mizoroki–Heck reaction. In contrast, the diastereomer 8c only led to the acenaphthylenes 12c and 13c through a domino carbopalladation/C–H activation reaction. Moreover, in the reaction of 20, 24 and 27 containing a naphthyl moiety only the tetra-substituted alkenes 23, 25/26 and 28/29, respectively were obtained, whereas in the reaction of 34, containing a phenanthrene moiety, compound 37 was the only product, formed via a C–H activation reaction.
A novel application of the Diels-Alder reaction: nitronaphthalenes as normal electron demand dienophiles
Paredes, Elisa,Brasca, Romina,Kneeteman, María,Mancini, Pedro M.E.
, p. 3790 - 3799 (2008/02/01)
Thermal reactions between nitronaphthalenes and butadienes were studied. It was demonstrated that these reactions are capable of undergoing the normal electron demand Diels-Alder reaction, with a variety of dienes affording the phenanthrene derivatives. The influence of the extension and type of substitution was also discussed. When the electron-withdrawing activation of the naphthalenic nucleus or the donor properties of the dienes were not enough, N-naphthylpyrroles were detected as main product, suggesting that a competitive reaction would probably take place. The results clearly confirmed the dienophilic nature of nitronaphthalenic double bonds and provided an alternative procedure for phenanthrene derivatives and N-naphthylpyrroles' synthesis. The relative reactivity of the reactants and the viability of the reactions were discussed from a theoretical point of view.
Nitronaphthalenes as Diels-Alder dienophiles
Paredes,Biolatto,Kneeteman,Mancini
, p. 8079 - 8082 (2007/10/03)
1-Nitronaphthalene, 2-nitronaphthalene and 1,3-dinitronaphthalene react with Danishefsky diene as normal electron demand Diels-Alder dienophiles to give hydroxyphenanthrene derivatives as principal products in reasonable yields. The aromatization is an ex
