Showing papers by "Dervilla M.X. Donnelly published in 1991"
TL;DR: The mechanism proposed for these reactions involves transfer of the aryl group onto copper forming a copper(III) intermediate which subsequently undergoes ligand coupling to give the N-arylated amine and the catalytic CuI species.
Abstract: Aryllead triacetates have been found to be regioselective reagents for the mono N-arylation of a range of aromatic, heterocyclic and aliphatic amines under mild and neutral conditions in a reaction catalysed by copper diacetate. The arylation of arylamines was unaffected by the steric hindrance of the arylamine but was dependent on the arylamine basicity. In addition, the position of oxidisable substituents on both the aryllead triacetate and the arylamine was found to be important due to a competing oxidation-reduction reaction. The arylation of heterocyclic amines proceeded in modest to good yields whilst aliphatic amines were arylated in poor to modest yields. The mechanism proposed for these reactions involves transfer of the aryl group onto copper forming a copper(III) intermediate which subsequently undergoes ligand coupling to give the N-arylated amine and the catalytic CuI species.
28 citations
TL;DR: In this paper, the synthesis of nomeolignan 2, isolated from Krameria ramosissima, was described. It proceeds in seven steps from trans-anethol in an overall yield of 14%.
9 citations
7 citations
TL;DR: The reaction of 2, 4, 6-trimethoxyphenyl-lead triacetate (4) with 3,5-di-t-butylphenol (1) at room temperature afforded the very hindered phenol (5) in good (87%) yield; acetylation gave the acetate (7) which was fully characterised, including an X-ray determination.
Abstract: The reaction of 2, 4, 6-trimethoxyphenyl-lead triacetate (4) with 3,5-di-t-butylphenol (1) at room temperature afforded the very hindered phenol (5) in good (87%) yield; acetylation gave the acetate (7) which was fully characterised, including an X-ray determination.
TL;DR: In this article, arylation of 3-hydroxycoumarins with aryl-lead triacetates followed by palladium-catalysed reduction of the derived 3-trifluoromethylsulphonyl-oxyarylcoumars is described.
Abstract: Neoflavonoids or 4-arylcoumarins are prepared by arylation of 3-hydroxycoumarins with aryl-lead triacetates followed by palladium-catalysed reduction of the derived 3-trifluoromethylsulphonyl-oxyarylcoumarins.
TL;DR: The mechanism proposed for these reactions involves transfer of the aryl group onto copper forming a copper(III) intermediate which subsequently undergoes ligand coupling to give the N-arylated amine and the catalytic CuI species.
Abstract: Aryllead triacetates have been found to be regioselective reagents for the mono N-arylation of a range of aromatic, heterocyclic and aliphatic amines under mild and neutral conditions in a reaction catalysed by copper diacetate. The arylation of arylamines was unaffected by the steric hindrance of the arylamine but was dependent on the arylamine basicity. In addition, the position of oxidisable substituents on both the aryllead triacetate and the arylamine was found to be important due to a competing oxidation-reduction reaction. The arylation of heterocyclic amines proceeded in modest to good yields whilst aliphatic amines were arylated in poor to modest yields. The mechanism proposed for these reactions involves transfer of the aryl group onto copper forming a copper(III) intermediate which subsequently undergoes ligand coupling to give the N-arylated amine and the catalytic CuI species.