78176-22-4Relevant academic research and scientific papers
Metal-Free C-Arylation of Nitro Compounds with Diaryliodonium Salts
Dey, Chandan,Lindstedt, Erik,Olofsson, Berit
, p. 4554 - 4557 (2015/09/28)
An efficient, mild, and metal-free arylation of nitroalkanes with diaryliodonium salts has been developed, giving easy access to tertiary nitro compounds. The reaction proceeds in high yields without the need for excess reagents and can be extended to α-arylation of nitroesters. Nitroalkanes were selectively C-arylated in the presence of other easily arylated functional groups, such as phenols and aliphatic alcohols.
α-Vinylation of 1,3-Dicarbonyl Compounds with Alkenyl(aryl)iodonium Tetrafluoroborates: Effects of Substituents on the Aromatic Ring and of Radical Inhibitors
Ochiai, Masahito,Shu, Toshifusa,Nagaoka, Takema,Kitagawa, Yutaka
, p. 2130 - 2138 (2007/10/03)
Direct α-vinylations of enolate anions derived from 1,3-dicarbonyl compounds with 4-teri-butyl-1- cyclohexenyl(aryl)iodonium 2 and 1-cyclopentenyl(aryl)iodonium tetrafluoroborates 3 are reported. Frequently, α-phenylations compete with the vinylations in the reaction of 1,3-dicarbonyl compounds with alkenyl(phenyl)iodonium salts 2a and 3a. Use of alkenyl(p-methoxyphenyl)iodonium salts 2b and 3b, however, leads to selective α-vinylation at the expense of the competing arylation of 1,3-dicarbonyl compounds. Use of an efficient aryl radical trap, 1,1-diphenylethylene, inhibits radical-induced decomposition of the alkenyl(aryl)iodonium salts, thereby improving the yields of α-vinylations of enolate anions derived from 1,3-dicarbonyl compounds.
The Chemistry of Aryllead(IV) Tricarboxylates. The C-Arylation of Nitroalkanes and Nitronate Salts with Aryllead Triacetates
Kozyrod, Robert P.,Pinhey, John T.
, p. 713 - 721 (2007/10/02)
2-Nitropropane reacts with phenyllead triacetate in dimethyl sulfoxide to give 2-nitro-2-phenylpropane in good yield.This arylation of nitroalkanes has been examined with a variety of substrates and a number of aryllead triacetates, and in those cases where there was no steric hindrance the reaction was found to be quite general.Reactions of nitroethane and methyl nitroacetate, compounds with two α-hydrogens, were readily controlled to give either the mono- or di-arylated products.The corresponding nitronate salts were also examined and found to undergo the arylation reaction in similar yield but at a very much faster rate.
The Arylation of Nitroalkanes and Nitronate Salts with Aryllead Triacetates
Kozyrod, Robert P.,Pinhey, John T.
, p. 783 - 784 (2007/10/02)
Nitroalkanes and their nitronate salts undergo α-arylation in good yield when treated with an aryllead triacetate in dimethyl sulfoxide.
