55136-97-5Relevant academic research and scientific papers
Rhenium-Catalyzed Dehydrogenative Coupling of Alcohols and Amines to Afford Nitrogen-Containing Aromatics and More
Mastalir, Matthias,Glatz, Mathias,Pittenauer, Ernst,Allmaier, Günter,Kirchner, Karl
supporting information, p. 1116 - 1120 (2019/05/16)
An efficient synthesis of quinolines, pyrimidines, quinoxalines, pyrroles, and aminomethylated aromatic compounds catalyzed by a well-defined Re(I) PNP pincer complex is described. All reactions proceed with liberation of dihydrogen and elimination of water. Under optimized reaction conditions a wide range of organic functional groups are tolerated. This study demonstrates that rhenium catalysts are performing extremely well in dehydrogenative processes with considerably lower catalyst loadings and shorter reaction times when compared to analogous Mn(I) complexes.
Manganese-Catalyzed Aminomethylation of Aromatic Compounds with Methanol as a Sustainable C1 Building Block
Mastalir, Matthias,Pittenauer, Ernst,Allmaier, Günter,Kirchner, Karl
supporting information, p. 8812 - 8815 (2017/07/12)
This study represents the first example of a manganese-catalyzed environmentally benign, practical three-component aminomethylation of activated aromatic compounds including naphtols, phenols, pyridines, indoles, carbazoles, and thiophenes in combination with amines and MeOH as a C1 source. These reactions proceed with high atom efficiency via a sequence of dehydrogenation and condensation steps which give rise to selective C-C and C-N bond formations, thereby releasing hydrogen and water. A well-defined hydride Mn(I) PNP pincer complex, recently developed in our laboratory, catalyzes this process in a very efficient way, and a total of 28 different aminomethylated products were synthesized and isolated yields of up to 91%. In a preliminary study, a related Fe(II) PNP pincer complex was shown to catalyze the methylation of 2-naphtol rather than its aminomethylation displaying again the divergent behavior of isoelectronic Mn(I) and Fe(II) PNP pincer systems.
The activation of aminals and aminol ethers by sulfur dioxide and their reactions with electron rich aromatic compounds
Heaney, Harry,Papageorgiou, George,Wilkins, Robert F.
, p. 13361 - 13372 (2007/10/03)
Reactions of bis(dialkylamino)methanes and ethoxydialkylaminomethanes with nucleophilic aromatic heterocycles in the presence of sulfur dioxide result in the formation of the expected Mannich bases in good yields. Reactions of phenols are similarly activated by sulfur dioxide which lead to improved regioselectivity: in particular the reactions of 2,5-dimethylphenol result in the formation of 2-dialkylaminomethyl-3,6-dimethylphenol whereas reaction occurs at the I-position using the classical procedures.
New Mannich Base Ligands
Hodgkin, Jonathan H.
, p. 2371 - 2378 (2007/10/02)
A series of low-molecular-weight aminomethylphenol compounds have been synthesized as model analogues of new Cu2+ and Fe3+ chelating polymers.Preliminary colour tests with these two ions were used to indicate the structural features
