932724-63-5Relevant articles and documents
Rapid Multialkylation of Aqueous Ammonia with Alcohols by Heterogeneous Iridium Catalyst under Simple Conditions
Yu, Han,Ma, Lin,Wada, Kenji,Kurihara, Ryohsuke,Feng, Qi,Uemura, Shinobu,Isoda, Kyosuke
, p. 3588 - 3593 (2021/07/02)
This paper reports the synthesis of tertiary and secondary amines from aqueous ammonia and benzylic alcohols by titania-supported iridium catalyst. It is a successful example of heterogeneous systems at moderate temperature without either additional solvent or high pressure. The catalytic system showed good tolerance to the atmosphere condition and performed rapidly to give tribenzylamine a yield of over 99 % within 6 hours in argon. The crystal structure of titania supports for iridium catalysts strongly affected their activity. The catalysis smoothly proceeded on larger scales. The catalyst could be easily reused and run at least for 5 cycles without significant loss of activity. The highly-dispersed iridium species of less than 2 nm in diameter would be responsible for the excellent catalytic activity. This catalyst is well applicable in multialkylation of aqueous ammonia with various primary and secondary benzylic alcohols.
Tris(8-methoxy-2-quinolylmethyl)amine (8-MeOTQA) as a highly fluorescent Zn2+ probe prepared by convenient C3-symmetric tripodal amine synthesis
Mikata, Yuji,Nodomi, Yuki,Ohnishi, Risa,Kizu, Asako,Konno, Hideo
, p. 8021 - 8030 (2015/05/13)
A convenient synthesis of C3-symmetric tribenzylamine (TBA) derivatives has been investigated. The reaction of benzyl chlorides with acetaldehyde ammonia trimer (1) in the presence of base afforded tribenzylamines in high yields. This efficient method allows the diverse synthesis of TPA (tris(2-pyridylmethyl)amine) and TQA (tris(2-quinolylmethyl)amine) derivatives. Among the TQA compounds prepared, tris(8-methoxy-2-quinolylmethyl)amine (8-MeOTQA, 4) exhibited superior properties as a fluorescent zinc probe with high quantum yield (Zn = 0.51) and high sensitivity (limit of detection (LOD) = 3.4 nM). The X-ray crystallographic analysis of [Zn(8-MeOTQA)]2+ revealed that the steric and electronic effect of 8-methoxy substituents kicks out the solvent and counterion molecules from the metal coordination sphere, resulting in short Zn-Nquinoline coordination distances (2.04-2.07 ?). The pseudo hexacoordinate complex of 6-methoxy derivative, [Zn(6-MeOTQA)(DMF)(ClO4)]+, exhibited longer Zn-Nquinoline distances (2.07-2.19 ?) and much smaller fluorescence intensity (Zn = 0.027). The replacement of one of the three 8-methoxyquinolines with pyridine also afforded much less fluorescent zinc complex (Zn = 0.095) due to the solvent coordination (Zn-Nquinoline = 2.05-2.18 ? for [Zn(8-MeOBQPA)(CH3OH)]2+).
Highly efficient heterogeneous gold-catalyzed direct synthesis of tertiary and secondary amines from alcohols and urea
He, Lin,Qian, Yue,Ding, Ran-Sheng,Liu, Yong-Mei,He, He-Yong,Fan, Kang-Nian,Cao, Yong
experimental part, p. 621 - 624 (2012/05/20)
Urea, the white gold: The efficient synthesis of tertiary and secondary amines is achieved by heterogeneous gold-catalyzed direct amination of stoichiometric alcohols with urea in good to excellent yields. Via a hydrogen autotransfer pathway, the reactions of primary alcohols with urea give tertiary amines exclusively, while secondary alcohols selectively afford secondary amines.
