947-72-8Relevant articles and documents
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De La Mare,Klassen,Koenigsberger
, p. 5285 (1961)
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Air-stable nickel precatalysts for fast and quantitative cross-coupling of aryl sulfamates with aryl neopentylglycolboronates at room temperature
Jezorek, Ryan L.,Zhang, Na,Leowanawat, Pawaret,Bunner, Matthew H.,Gutsche, Nicholas,Pesti, Aleksander K. R.,Olsen, James T.,Percec, Virgil
supporting information, p. 6326 - 6329 (2015/02/19)
A library containing 10 air-stable NiIIX(Aryl)(PCy3)2 complexes as precatalysts (X = Cl, Br, OTs, OMs, aryl = 1-naphthyl, 2-naphthyl; X = Cl, 1-acenaphthenyl, 1-(2-methoxynaphthyl), 9-phenanthrenyl, 9-anthracyl) was synthesized and demonstrated to quantitatively cross-couple 2-methoxyphenyl dimethylsulfamate with methyl 4-(5,5-dimethyl-1,3,2-dioxaborinane-2-yl)benzoate at 23 °C in dry THF in the presence of K3PO4(H2O)3.2 in less than 60 min. Lower or higher amounts of H2O in K3PO4 and as received THF mediate the same transformation in a maximum three times longer reaction time.
Nucleophilic substitution of hydrogen in naphthalene by chloride (Cl -) in ionic liquids
Shi, Shen Yi,Kong, Ai Guo,Zhao, Xin Hua,Ding, Han Ming,Yang, Fan,Shan, Yong Kui
experimental part, p. 147 - 150 (2012/01/03)
Nucleophilic aromatic substitution of hydrogen in non-activated aromatic ring, a very rare phenomenon in organic chemistry, is found in ionic liquids containing Cl- as anion under mild reaction conditions. The reaction may be carried out by the addition of the halogen-bonding adduct (Br 2Cl-) as nucleophile to aromatic ring carbon atom, leading to the formation of the nucleophilic substitution product.
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.