21236-74-8Relevant articles and documents
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.
Reaction on a solid surface - A simple, economical, and efficient Mannich reaction of azacrown ethers over graphite
Sharghi, Hashem,Khalifeh, Reza
, p. 426 - 434 (2008/09/20)
Graphite brings about a rapid Mannich reaction with a range of activated and unactivated phenolic compounds such as p-cresol and p-nitrophenol. The reactions are carried out with azacrown ether and paraformaldehyde in solvent-free conditions at 100 °C for 20-30 min. The graphite powder can be reused up to three times after simple washing with acetone.
2-(2-Amino-2-methylpropyl)phenols by C-C-Linkage of 2-Hydroxybenzyl Alcohols with 2-Nitropropane Anions
Diery, Helmut,Renger, Bernd
, p. 1239 - 1251 (2007/10/02)
The 2-hydroxybenzyl alcohols 1, 6, 8a, and 8e can be converted into the 2-(2-methyl-2-nitropropyl)-phenols 2, 7, and 9 by a SRN1-reaction with the sodium salt of 2-nitropropane.Catalytic hydrogenation yields the amines 3 and 10.The consequent reactions - leading to the quaternary salts 13 and 14 and as to the addition-compounds 15 and 16 - are negatively influenced by the strong steric shielding of the amino groups.