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A class of biaryl monophosphine ligands containing naphthofuran structure and its preparation method and application
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A technology for biaryl monophosphine ligands, applied in the field of biaryl monophosphine ligands and their preparation
Active Publication Date: 2018-04-06
SUN YAT SEN UNIV
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Although many monophosphine ligands have been reported, due to the diversity of substrates and reactions, the requirements for ligands are also diverse. Therefore, it is urgent to develop phosphine ligands with different structures to meet different reaction types. needs
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Embodiment 1
[0048] Embodiment 1 biaryl monophosphine ligand
[0049] In this embodiment, the biaryl monophosphine ligand represented by the formula ((+)-8A) is taken as an example to introduce its preparation process.
[0050]
[0051] (1), use compound shown in formula ((+)-1) to prepare compound shown in formula ((+)-2)
[0052]
[0053]Under nitrogen protection, dissolve 1.0g (2.13mmol) of the compound represented by formula ((+)-1) in 50mL of ethanol, add 10mL of 4mol / L dilute hydrochloric acid, react at 80°C for 7h, spin dry the ethanol under reduced pressure, and then add 100mL Dissolve in water, extract 3 times with ethyl acetate, combine the organic phases, wash with saturated brine, dry over anhydrousmagnesiumsulfate, and remove the solvent under reduced pressure to obtain 850 mg of the product formula ((+)-2) through silica gelcolumn chromatography. Shown compound, yield: 93%, product analysis result: [α] D 17 +47.5 (c=0.1, CHCl 3 ), 1 H NMR (400MHz, CDCl 3 )δ8.48...
Embodiment 2
[0076]
[0077] In the glove box, Sm1 (0.1mmol, 1.0equiv), Sm2 (0.2mmol, 2.0equiv), K 3 PO 4 (0.3mmol, 3.0equiv), Pd 2 (dba) 3 (1.0% mmol), (±)-8A (2.0% mmol) and toluene (4.0 mL) were placed in a 25 mL one-necked bottle, and stirred at 80° C. for 1 hour under nitrogen protection. Product result analysis: 1 H NMR (400MHz, CDCl 3 )δ8.05-8.01(3H,m),7.95(1H,d,J=8.0Hz),7.69(1H,t,J=4.0Hz),7.52-7.49(3H,m),7.40-7.23(5H ,m),3.81(3H,s). 13 C NMR (101MHz, CDCl 3 )δ154.6, 134.6, 134.3, 133.7, 133.0, 129.5, 129.0, 128.5, 128.2, 127.8, 126.2, 125.7, 125.6, 125.5, 123.6, 123.2, 113.8, 56.8.
Embodiment 3
[0079]
[0080] In the glove box, Sm1 (0.1mmol, 1.0equiv), Sm3 (0.2mmol, 2.0equiv), K 3 PO 4 (0.3mmol, 3.0equiv), Pd 2 (dba) 3 (1.0% mmol), (±)-8A (2.0% mmol) and isopropanol (4.0 mL) were placed in a 25 mL one-necked bottle, and stirred at 80° C. for 4 hours under nitrogen protection. Product result analysis: 1 H NMR (400MHz, CDCl 3 )δ8.70-8.68 (1H, m), 8.66 (1H, s), 7.97 (1H, d, J = 12.0Hz), 7.87 (1H, t, J = 4.0Hz), 7.76-7.73 (1H, m ),7.50-7.45(2H,m),7.42-7.38(3H,m),3.87(3H,s). 13 C NMR (101MHz, CDCl 3 )δ154.1, 151.8, 148.2, 138.6, 133.3, 130.0, 128.9, 128.1, 126.8, 124.5, 123.7, 123.1, 133.3, 56.5.
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Abstract
The invention discloses naphthofuran-structure-containing biaryl monophosphine ligands, and a preparation method and application thereof. The biaryl monophosphine ligands are compounds disclosed the chemical structural formula (VIII) or antipodes or racemates thereof. According to the biaryl monophosphine ligands, the furan ring is introduced and forms a conjugated structure with the dinaphthalene, thereby increasing the steric hindrance of the phosphine ligands (including antipodes or racemates thereof) and the cloud density of the aromatic ring, and enhancing the stability of the complexes. The steric hindrance of the ligands is regulated, so that the ligands have novel structure. The preparation process comprises the steps of Sonogashira reaction, intramolecular cyclization, C-P coupling reaction and the like. The synthesis method is simple; and the obtained ligands have the advantages of high activity, favorable selectivity and the like when being used for Suzuki-Miyuara reaction.
Description
technical field [0001] The invention belongs to the field of chemical catalysis, and in particular relates to a class of biaryl monophosphine ligands containing naphthofuran structures and a preparation method and application thereof. Background technique [0002] In catalytic reactions, the coordination of substrates, catalysts and ligands is very important, and small changes in ligand structures often have a series of effects on the activity, selectivity and kinetics of catalytic reactions. [0003] The outer electron configuration of the ground state of the phosphorus atom is 3s 2 threesome 3 , which takes the inequality sp 3 The hybrid orbital forms three σ bonds with three substituents (alkyl, aryl or alkoxy, aryloxy) respectively. Electronic effect and steric effect are two important aspects of organophosphine ligands affecting catalytic reactions. In recent years, in the design process of ligands, a series of electron-rich and large steric hindrance phosphine ligan...
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