A kind of preparation method of 1-naphthol-based phosphine oxygen ligand
A naphthol-based phosphine and ligand technology is applied in the field of preparation of 1-naphthol-based phosphine oxygen ligands, and can solve the problems affecting the development and application of ligands, harsh conditions, difficult handling, etc., and achieves high yield and reaction Mild conditions and good substrate adaptability
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Embodiment 1
[0011] Preparation (2-phenyl-4-hydroxyaphthyl) diphenyl phosphate, structural formula:
[0012] In a 25 ml Schlenk tube equipped with a magnetized 25 ml Schlenk tube, phenylthynthyldin-based phenyl phosphate (0.1 mmol), benzoyl sulfur, 6.66 mg (0.008 mmol, 8%) [RHCP * (CH 3 CN) 3 ] (SBF 6 ) 2 5.5 mg (0.03 mmol, 30%) zinc acetate, then add 4.0 ml of dried DCE, placed in a preheated 80 ° C oil bath, reacted in a nitrogen atmosphere for 16 h, and the reaction is removed from the heat source, then Dichloromethane was added to the round bottom flask, and the solvent was removed with a rotary evaporator, ethyl acetate / dichloromethane = 1: 3 over silica gel columns to obtain 38.6 mg of the target product, and the yield was 92%.
[0013] The characterization of the compound is as follows:
[0014] 1 H NMR (400MHz, DMSO): δ 10.48 (S, 1H), 8.24 (D, J = 8.2 Hz, 1H), 7.60-7.54 (m, 1H), 7.54-7.37 (M, 11H), 7.20-7.12 (m, 2H), 7.04 (t, j = 7.6 Hz, 2H), 6.99-6.89 (m, 3H);
[0015] 13 C NMR (10...
Embodiment 2
[0019] Preparation (7-methyl-2-phenyl-4-hydroxyapanedaphthyl) diphenyrophosphate, structural formula:
[0020] In a 25 ml Schlenlenk tube with a magnetized, phenylethynthyne phenyl phosphate (0.1 mmol), 4-methylbenzoyl sulfur, and 6.66 mg (0.008 mmol, 8) were added. %) [RHCP * (CH 3 CN) 3 ] (SBF 6 ) 2 5.5 mg (0.03 mmol, 30%) zinc acetate, then add 4.0 ml of dried DCE, placed in a preheated 80 ° C oil bath, reacted in a nitrogen atmosphere for 16 h, and the reaction is removed from the heat source, then Dichloromethane was added to the round bottom flask, and the solvent was removed with a rotary evaporator, ethyl acetate / dichloromethane = 1: 3 over silica gel columns were 32.0 mg of the target product, and the yield was 74%.
[0021] The characterization of the compound is as follows:
[0022] 1 H NMR (400MHz, DMSO): Δ10.42 (S, 1H), 8.14 (D, J = 8.5 Hz, 1H), 7.53-7.46 (m, 6H), 7.39 (TD, J = 8.1, 2.1 Hz, 5H ), 7.15 (DD, J = 10.5, 4.03 (T, J = 7.6 Hz, 2H), 6.94 (S, 1H), 6.89 (DD,...
Embodiment 3
[0027] Preparation of (2-phenyl-4-hydroxy-7-methoxynylmethyl) diphenyl oxygen, structural formula:
[0028] Aphenyl Schlenlenk tube equipped with a magnetized 25 ml Schlenk tube was added to add phenylacetyl diphenyl phosphate (0.1 mmol), 4-methoxybenzyl sulfur, 6.66 mg (0.008 mmol, 8%) [RHCP * (CH 3 CN) 3 ] (SBF 6 ) 2 5.5 mg (0.03 mmol, 30%) zinc acetate, then add 4.0 ml of dried DCE, placed in a preheated 80 ° C oil bath, reacted in a nitrogen atmosphere for 16 h, and the reaction is removed from the heat source, then Dichloromethane was added to the round bottom flask, and the solvent was removed with a rotary evaporator, ethyl acetate / dichloromethane = 1: 3 paste the silica gel column to obtain 35.3 mg of the target product, and the yield was 78%.
[0029] The characterization of the compound is as follows:
[0030] 1 H NMR (400MHz, DMSO): Δ10.39 (S, 1H), 8.16 (D, J = 9.2 Hz, 1H), 7.50 (DD, J = 10.7, 7.8 Hz, 6H), 7.43-7.37 (M, 4H ), 7.25 (DD, J = 9.2, 2.5 Hz, 1H), 7.15 (T, ...
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