- Nickel-catalyzed cross-coupling of aryltrimethylammonium iodides with organozinc reagents
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Broad scope and good tolerance: An efficient cross-coupling of aryltrimethylammonium iodide salts with aryl-, methyl-, and benzylzinc chlorides catalyzed by [Ni(PCy3)2Cl2] has been achieved (see scheme). The reaction involves cleavage of the C-N bond and displays broad substrate scope and good functional group tolerance. NMP=N-methylpyrrolidine. Copyright
- Xie, Lan-Gui,Wang, Zhong-Xia
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supporting information; experimental part
p. 4901 - 4904
(2011/06/22)
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- ACTIVATING ACTION OF THE IMMONIUM GROUP IN THE SUBSTITUTION OF ALKOXYL AND HALOGEN ATOMS BY THE ALKYLAMINO GROUP IN THE BENZENE RING
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The substitution of the alkoxy group in o-, p-, and m-alkoxybenzylidenedimethylimmonium iodides by the action of aliphatic amines was investigated.Only p-alkoxy derivatives enter into the reaction forming, after hydrolysis, p-alkyl- and p-dialkylaminobenzaldehydes.Substitution can also be realized in p-alkoxybenzaldehydes and Schiff bases in the presence of the amine hydrochloride.Similarly, the halogen atom in p-halogenobenzaldehydes is substituted by the aliphatic amine residue.Quantum-mechanical calculations of the energy of anionic localization and charge at the attacked carbon atom o f the benzene ring are consistent with the experimantal data.
- Yudin, L. G.,Blokhin, A. V.,Bundel', Yu. G.,Simkin, B. Ya.,Terenin, V. I.
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p. 2064 - 2068
(2007/10/02)
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