Chiral trivalent gold complex and its preparation method and application
A gold complex and chiral technology, applied in the field of stable chiral trivalent gold complexes and their preparation, can solve the problems of poor stability of trivalent gold salts, unsuitability as catalysts, poor functional group compatibility, etc., and achieve catalytic Balanced activity, excellent chemoselectivity and regioselectivity, and improved stability
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[0046] Correspondingly, a preparation method of a chiral trivalent gold complex comprises the following steps:
[0047]S01. Provide racemic or optically active binaphthol derivatives with structure as described in formula 1, oxazoline-gold(III) dichloride with structure as described in formula 2 or oxazoline-gold (III) dichloride with structure as described in formula 3 2-substituted pyridine-gold (III) dichloride;
[0048] S02. The binaphthol derivatives, oxazoline-gold (III) dichloride or 2-substituted pyridine-gold (III) dichloride are dissolved in an organic solvent, and the following chemical reaction occurs under the presence of an alkali , to obtain a chiral trivalent gold complex, the general reaction formula is as follows:
[0049]
[0050] Specifically, in the above step S01, the binaphthol derivatives, oxazoline-gold(III) dichloride, and 2-substituted pyridine-gold(III) dichloride can be purchased or prepared by themselves. The selection of each substituent in ...
Embodiment 1
[0074] Embodiment 1: the synthesis of gold (III) complex (R)-1
[0075]
[0076] S-configuration of binaphthol (S)-1,1'-binaphthol (0.22mmol), 2-[2'-(4',4'-dimethyl based on oxazoline ligand skeleton )Oxazolinyl]phenylgold dichloride (0.20mmol), anhydrous cesium carbonate (0.44mmol) and methanol (10mL) were placed in a 25mL round bottom flask. Stir at room temperature, and observe that orange-red precipitates are slowly produced. After 2 hours of reaction, TLC detection (ethyl acetate:petroleum ether 1:3) completes the reaction, filters, and the resulting orange-red solid is washed with an appropriate amount of methanol (or through a silica gel column Chromatography) to obtain gold (III) complex (R)-1 (112 mg, yield 85%) in the R-configuration as an orange-red solid. 1H NMR (400MHz, CDCl3) δ7.92(d, J=9.9Hz, 1H), 7.67(dd, J=9.1, 3.6Hz, 2H), 7.52(d, J=7.1Hz, 1H), 7.47(d ,J=7.8Hz,1H),7.36–7.30(m,2H),7.25–7.15(m,4H),7.13(dd,J=10.8,4.3Hz,1H),7.07–6.94(m,2H), 6.77(dd, J=6.3,3....
Embodiment 2
[0077] Embodiment 2: the synthesis of gold (III) complex (S)-1
[0078]
[0079] R-configured binaphthol (S)-1,1'-binaphthol (0.22mmol), 2-[2'-(4',4'-dimethyl based on oxazoline ligand skeleton )Oxazolinyl]phenylgold dichloride (0.20mmol), anhydrous cesium carbonate (0.44mmol) and methanol (10mL) were placed in a 25mL round bottom flask. Stir at room temperature, and observe that orange-red precipitates are slowly produced. After 2 hours of reaction, TLC detection (ethyl acetate:petroleum ether 1:3) completes the reaction, filters, and the resulting orange-red solid is washed with an appropriate amount of methanol (or through a silica gel column Chromatography) to obtain gold (III) complex (S)-1 (115 mg, yield 88%) as an orange-red solid in R-configuration. 1 H NMR (400MHz, CDCl3) δ7.92(d, J=9.9Hz, 1H), 7.67(dd, J=9.1, 3.6Hz, 2H), 7.52(d, J=7.0Hz, 1H), 7.47(d ,J=7.8Hz,1H),7.37–7.29(m,2H),7.21(ddd,J=14.1,8.2,4.4Hz,4H),7.13(dd,J=10.8,4.3Hz,1H),7.06– 6.96(m,2H),6.77(dd,J=6....
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