Gonzalez-Lainez, Miguel; Jimenez, M. Victoria; Azpiroz, Ramon; Passarelli, Vincenzo; Modrego, F. Javier; Perez-Torrente, Jesus J. published the artcile< N-Methylation of Amines with Methanol Catalyzed by Iridium(I) Complexes Bearing an N,O-Functionalized NHC Ligand>, Safety of 2-Methoxy-N-methylaniline, the main research area is iridium complex imidazolylidenelutidine polydentate ligand preparation catalyst methylation aniline; crystal structure iridium complex containing imidazolylidenelutidine polydentate ligand; mol structure iridium complex containing imidazolylidenelutidine polydentate ligand.
A set of neutral [IrBr(L2)(κC-tBuImCH2PyCH2OMe)] and cationic [Ir(L2)(κ2C,N-tBuImCH2PyCH2OMe)]PF6 (L2 = cod, (CO)2) Ir(I) compounds featuring a flexible lutidine-derived polydentate ligand having NHC and -OMe as donor functions were evaluated as catalyst precursors for the N-methylation of aniline using MeOH both as a reducing agent and a C1 source. The carbonyl complexes are somewhat more active than the related diene compounds with the neutral compound [IrBr(CO)2(κC-tBuImCH2PyCH2OMe)] being the more active. A range of aromatic primary amines, including heterocyclic amines, were selectively transformed into the corresponding N-methylamino derivatives using this catalyst at a low catalyst loading (0.1 mol %) and substoichiometric amounts of Cs2CO3 (half equiv) as a base, in MeOH at 423 K. For aliphatic primary amines, selective N,N-dimethylation was achieved under the same catalytic conditions. The unselective deprotonation of the methylene linkers in [IrBr(CO)2(κC-tBuImCH2PyCH2OMe)] affords two isomeric neutral complexes featuring a coordinated dearomatized pyridine core, which were converted into [Ir(OMe)(CO)2(κC-tBuImCH2PyCH2OMe)] upon addition of MeOH. This compound undergoes thermal activation of a C-H bond of the tert-Bu group to give the cyclometalated Ir(I) complex [Ir(CO)2{κ2C,C-(-CH2Me2C-ImCH2PyCH2OMe)}] featuring a bidentate C,C-coordinated NHC ligand. Mechanistic studies support a borrowing H mechanism proceeding through Ir(I) intermediates with the methoxo complex as the catalytic active species and the cyclometalated complex as the catalyst resting state. D labeling experiments demonstrated that both species are in equilibrium under catalytic conditions, which is consistent with the exhibited catalytic activity of the cyclometalated complex.
Organometallics published new progress about Amines Role: RCT (Reactant), RACT (Reactant or Reagent). 10541-78-3 belongs to class ethers-buliding-blocks, and the molecular formula is C8H11NO, Safety of 2-Methoxy-N-methylaniline.
Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem