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.
Regioselective mannich reaction of phenols under high pressure using dichloromethane as C1 unit
Matsumoto, Kiyoshi,Joho, Kouta,Mimori, Seisuke,Iida, Hirokazu,Hamana, Hiroshi,Kakehi, Akikazu
scheme or table, p. 1061 - 1067 (2009/06/28)
Regioselectivity in Mannich reaction of 4-, 3-, and 2-substituted phenols with typical heterocyclic amines are investigated under reaction conditions developed by us. Phenol and 4-alkyl, and 4-chlorophenols in the title reaction predominantly gave the corresponding 2-(aminomethyl)phenols, while 4-methoxyphenol afforded, in addition to the mono(aminomethyl)phenols, a considerable amount of the bis adducts. Peculiarly enough, 3-methylphenol with amines afforded 3-methyl-4-(aminomethyl)phenols whereas 2-methylphenol produced 2-methyl-6-(aminomethyl)phenols.
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.