17310-99-5Relevant articles and documents
Nickel-catalyzed cross-coupling of aryltrimethylammonium iodides with organozinc reagents
Xie, Lan-Gui,Wang, Zhong-Xia
supporting information; experimental part, p. 4901 - 4904 (2011/06/22)
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
ACTIVATING ACTION OF THE IMMONIUM GROUP IN THE SUBSTITUTION OF ALKOXYL AND HALOGEN ATOMS BY THE ALKYLAMINO GROUP IN THE BENZENE RING
Yudin, L. G.,Blokhin, A. V.,Bundel', Yu. G.,Simkin, B. Ya.,Terenin, V. I.
, p. 2064 - 2068 (2007/10/02)
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.
