1009080-91-4Relevant academic research and scientific papers
The fluxional amine gold(III) complex as an excellent catalyst and precursor of biologically active acyclic carbenes
Montanel-Pérez, Sara,Herrera, Raquel P.,Laguna, Antonio,Villacampa, M. Dolores,Gimeno, M. Concepción
, p. 9052 - 9062 (2015)
A new amine gold(III) complex [Au(C6F5)2(DPA)]ClO4 with the di-(2-picolyl)amine (DPA) ligand has been synthesised. In the solid state the complex has a chiral amine nitrogen because the ligand coordinates to the gold centre through one nitrogen atom from a pyridine and through the NH moiety, whereas in solution it shows a fluxional behaviour with a rapid exchange between the pyridine sites. This complex can be used as an excellent synton to prepare new gold(III) carbene complexes by the reaction with isocyanide CNR. The resulting gold(III) derivatives have unprecedented bidentate C∧N acyclic carbene ligands. All the complexes have been spectroscopically and structurally characterized. Taking advantage of the fluxional behaviour of the amine complex, its catalytic properties have been tested in several reactions with the formation of C-C and C-N bonds. The complex showed excellent activity with total conversion, without the presence of a co-catalyst, and with a catalyst loading as low as 0.1%. These complexes also present biological properties, and cytotoxicity studies have been performed in vitro against three tumour human cell lines, Jurkat (T-cell leukaemia), MiaPaca2 (pancreatic carcinoma) and A549 (lung carcinoma). Some of them showed excellent cytotoxic activity compared with the reference cisplatin.
Cyclometallated gold(III) complexes as effective catalysts for synthesis of propargylic amines, chiral allenes and isoxazoles
Kung, Karen Ka-Yan,Lo, Vanessa Kar-Yan,Ko, Hok-Ming,Li, Gai-Li,Chan, Pui-Ying,Leung, King-Chi,Zhou, Zhongyuan,Wang, Ming-Zhong,Che, Chi-Ming,Wong, Man-Kin
, p. 2055 - 2070 (2013/08/23)
A series of cyclometallated gold(III) complexes [Au(CN)Cl2] 1a-l (HCN=arylpyridines) and a PEG-linked complex 1m were synthesized. Complexes 1a-m are effective in catalyzing the synthesis of propargylic amines, chiral allenes and isoxazoles. Six-membered ring cyclometallated gold(III) complexes 1f-l exhibited higher catalytic activity than five-membered ring cyclometallated gold(III) complexes 1a-e. The diastereoselectivity of propargylic amines could be tuned by using chiral aldehyde and/or amine substrates. Excellent enantioselectivities (90-98% ee) were achieved in chiral allene synthesis. Chiral allene racemization could be minimized by using 1f as catalyst. The PEG-linked catalyst 1m is the most catalytically active towards synthesis of propargylic amines, in which case a product turnover of 900 was achieved. Moreover, 1m could be repeatedly used for 12 reaction cycles, leading to an overall turnover number of 872. Copyright
Gold(III) (C^N) complex-catalyzed synthesis of propargylamines via a three-component coupling reaction of aldehydes, amines and alkynes
Lo, Vanessa Kar-Yan,Kung, Karen Ka-Yan,Wong, Man-Kin,Che, Chi-Ming
experimental part, p. 583 - 591 (2009/06/05)
Propargylamines are synthesized in high yields via a gold(III) (C^N) complex-catalyzed three-component coupling reaction of aldehydes, amines and alkynes in water at 40 °C. Excellent diastereoselectivities (up to 99:1) have been achieved when chiral prolinol derivatives are employed as the amine component. Notably, the [Au(C^N)Cl2] complex (N^CH = 2-phenylpyridine) could be repeatedly used for 10 reaction cycles, leading to an overall turnover number of 812.
