Silicon-center chiral silicon-oxygen compound and preparation method thereof

A technology of silicon oxide compounds and compounds, applied in the direction of silicon organic compounds, chemical instruments and methods, compounds of group 4/14 elements of the periodic table, etc., can solve the limitation of chiral silicon compound design and application, and cannot obtain satisfactory ee value , limited range of substrates, etc., to achieve the effects of wide application range of substrates, excellent glum value, and atom economy

Active Publication Date: 2021-07-23

SOUTH UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA

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AI-Extracted Technical Summary

Problems solved by technology

Although there are many methods for synthesizing siloxanes and silyl ethers, methods for obtaining chiral center compounds are rarely reported, which limits the design and application of chiral silicon compounds.

[0003] At present, silicon chiral silyl et...

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Method used

[0124] Using the Josiphos ligand L4 exchanged by the substituent of the phosphorus atom, the yield and enantioselectivity were significantly i...

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Abstract

The invention belongs to the field of chiral silicon synthesis, and discloses a silicon-center chiral silicon-oxygen compound. The compound has a structure represented by general formula I shown in the specification. In the formula I, X is Si(R<3>)n or a formula also shown in the specification, R<1> is selected from alkyl, cycloalkyl and aryl, R<2> is selected from alkyl, substituted phenyl and aryl, R<3> is selected from alkyl, phenyl and substituted phenyl, n is 3, the three R<3> are the same or different, R<4> is selected from hydrogen and (C1-C4) alkyl, m is selected from 0, 1, 2 and 3, and Y is selected from substituted phenyl, substituted pyrenyl, aryl, heteroaryl and cycloalkyl. The invention also discloses a preparation method of the compound. Various highly functionalized chiral siloxanes and silyl ethers are obtained with good chemical, regional and stereo control and high yield, the variety of silicon center chiral compounds is expanded, and the method has the advantages of high enantioselectivity, wide substrate application range, mild reaction conditions, atom economy and the like. In addition, the compound provided by the invention has a huge application prospect in chiral organic photoelectric materials.

Application Domain

Silicon organic compoundsBulk chemical production

Technology Topic

Oxygen compoundSilyl ether +13

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Examples

Experimental program(41)

Example Embodiment

[0086] Example 1

[0087] Synthesis of dihydrosilane substrate

[0088]

[0089] Method A: TBULi (1.3M pentane solution, 1.1 equivalents) were added dropwise to the aryl bromide (1.0 equivalent) of THF (0.5 m) solution under -78 ° C, argon, and stirred at -78 ° C 1h, then add TBusicl in 10ml THF 3 (1.2 equivalents). The mixture was stirred at -78 ° C for 1 h, then warmed to room temperature and stirred overnight. Cooling the reaction again to -78 ° C and dropped with LiAlh 4 (2.5 m THF solution, 2.0 equivalents), and stirred at -78 ° C for 30 min, then the mixture was hot to room temperature and stirred for 8 h. Finally, the reaction mixture is saturated at -78 ° C NH. 4 Cl to quench, increase the mixture after rising to room temperature, use ET 2 O Wash, combine organic layers and use MGSO 4 Dry, filtrate, evaporate under reduced pressure. The crude mixture was purified by silica gel column chromatography (100% petroleum ether) to give dihydrosilane.

[0090]

[0091] Method B: TBULI (1.3 m pentane solution, 1.1 equivalents) was added dropwise to THF (40 mmol) of THF (40 ml) of THF (40 mL), and mixture was stirred at 0 ° C for 1 h at 0 ° C. Warm until room temperature and stir for 8 h, cool to 0 ° C, and liAlh 4 (2.5 M THF solution, 2.0 eq.) And stirred at 0 ° C for 30 min. The mixture was then warmed to room temperature and stirred for 8 h, and finally, the reaction mixture was saturated at 0 ° C NH. 4 Cl to quench, raised to room temperature, filtrate the mixture, use ET 2 O Wash, combine organic layers and use MGSO 4 Dry, filtrate, evaporate under reduced pressure.

[0092] The crude mixture was purified by silica gel column chromatography (100% petroleum ether) to give dihydrosilane.

[0093]

[0094] The product 1a is a colorless liquid (RF = 0.7, petroleum ether) with a yield of 74% (720 mg). Character data: 1 H NMR (400MHz, CDCL 3 Δ7.49 (D, J = 8.4 Hz, 2H), 6.91 (D, J = 4.8 Hz, 2H), 4.12 (S, 2H), 3.00 (S, 3H), 1.00 (s, 9h). 13 C NMR (151MHz, CDCL 3 δ161.02, 137.51, 123.10, 113.80, 55.16, 27.52, 16.60. HRMS (ESI, M / Z) Accurate Quality Calculation C 11 Hide 19 OSI [M + H + ]: 195.1200, measured value: 195.1224.

[0095] Preparation according to method a, the product 1b is a white solid (RF = 0.3, petroleum ether / ethyl acetate = 20: 1), the yield is 40% (300 mg). Character data: 1 H NMR (400MHz, CDCL 3 Δ7.47 (D, J = 8.4 Hz, 2H), 6.90 (D, J = 8.8 Hz, 2H), 4.11 (S, 2H), 3.86 (T, J = 4.8 Hz, 4H), 3.20 (T, J = 4.8Hz, 4H), 1.00 (s, 9h). 13 CNMR (101 MHz, CDCL 3 Δ152.18, 137.22, 121.57, 114.75, 67.00, 48.64, 27.54, 16.66. HRMS (ESI, M / Z) precision quality calculation C 14 Hide 24 Nosi [M + H + ]: 250.1622, measured value: 250.1617.

[0096] According to method a, the product 1c is a colorless oil (RF = 0.8, petroleum ether), and the yield is 55% (300 mg). Character data: 1 H NMR (400MHz, CDCL 3 Δ7.56-7.52 (m, 2H), 7.08-7.04 (m, 2H), 4.14 (S, 2H), 1.00 (s, 9h). 13 C NMR (101MHz, CDCL 3 Δ164.28 (d, j CF = 248.8Hz), 137.97 (D, J CF = 7.7Hz), 127.80 (D, J CF = 4.0Hz), 115.27 (D, J CF = 19.7 Hz), 27.46, 16.51. 19 F NMR (376MHz, CDCL 3 Δ-111.00. HRMS (ESI, M / Z) Accurate Quality Calculation C 10 Hide 16 FSI [M + H + ]: 183.1000, measured value: 183.1020.

[0097] According to method B, the product 1d is a colorless liquid (RF = 0.8, petroleum ether), and the yield is 53% (1.74 g). Epigemonary data: 1 H NMR (600MHz, CDCL 3 Δ7.57 (D, J = 7.2 Hz, 2H), 7.41-7.25 (m, 3H), 4.15 (S, 2H), 1.02 (S, 9H). 13 C NMR (151MHz, CDCL 3 δ136.04, 132.38, 129.68, 127.96, 27.58, 16.56. HRMS (ESI, M / Z) Accurate Quality Calculation C 10 Hide 17 Si [M + H + ]: 165.1094, measured value: 165.1069.

[0098] According to method a, the product 1e is a colorless oil, which is mixed with naphthalene (N / N = 2: 1) (RF = 0.7, petroleum ether), and the yield is 60% (423 mg). Character data: 1 H NMR (400MHz, CDCL 3 δ8.14 (D, J = 7.7 Hz, 1H), 7.89 (D, J = 8.4 Hz, 1H), 7.84 (D, J = 1.5 Hz, 1H), 7.78 (D, J = 6.8 Hz, 1H) , 7.49-7.46 (m, 3H), 4.52 (S, 2H), 1.05 (S, 9H). 13 C NMR (101MHz, CDCL 3 Δ137.63, 137.17, 133.60, 131.30, 133.62, 128.90, 128.87, 126.13, 125.80, 125.16, 28.27, 17.49. HRMS (ESI, M / Z) Accurate Quality Calculation C 14 Hide 19 Si [M + H + ]: 215.1250, measured value: 215.1289.

[0099] According to method a, the product 1f is a pale yellow solid (RF = 0.7, petroleum ether), and the yield is 47% (690 mg). Character data: 1 H NMR (600MHz, CDCL 3 Δ8.40 (D, J = 9.0 Hz, 1H), 8.23 (D, J = 7.2Hz, 1H), 8.17 (T, J = 7.8 Hz, 2H), 8.13-8.07 (M, 3H), 8.04- 7.98 (m, 2H), 4.72 (S, 2H), 1.08 (S, 9H). 13 C NMR (151MHz, CDCL 3 δ136.60, 135.47, 132.80, 131.38, 13.90, 128.49, 128.38, 128.29, 127.62, 127.61, 126.05, 125.44, 125.41, 124.78, 124.63, 124.12, 28.22, 17.85. HRMS (APCI, M / Z) Precise Quality Calculation C 20 Hide 21 Si [M + H + ]: 289.1407, measured value: 289.1418.

[0100]

[0101] Method C: R-MGBR was added to the stirred chloropenzylsilane (7.5 mmol, 1.5 equivalent) THF (15 ml) solution, 1.0 equivalent) in THF, 1.0 equivalents), then The reaction mixture was hot to room temperature and stirred for 2 h, and after cooling to 0 ° C, saturated NH 4 CL solution, mixture with ET 2 O extraction 3 times, the combined organic layer is MgSO 4 Dry, evaporate under reduced pressure. The crude mixture was purified by silica gel column chromatography (100% petroleum ether) to give dihydrosilane.

[0102]

[0103] According to method C, the product 1 g is a colorless oil (RF = 0.8, petroleum ether), and the yield is 88% (660 mg). Character data: 1 H NMR (400MHz, CDCL 3Δ7.57 (DD, J = 7.6, 1.5 Hz, 2H), 7.41-7.33 (M, 3H), 4.18 (D, J = 2.9 Hz, 2H), 1.26-1.16 (m, 1H), 1.08 (D , J = 7.2Hz, 6H). 13 C NMR (151MHz, CDCL 3 δ 135.71, 132.35, 129.65, 128.05, 18.98, 10.84.

[0104] According to method C, the product is 1 h is a colorless oil (RF = 0.8, petroleum ether), and the yield is 78% (741 mg). Character data: 1 H NMR (400MHz, CDCL 3 Δ7.55 (DD, J = 7.0, 1.9 Hz, 2H), 7.39-7.34 (M, 3H), 4.16 (D, J = 2.9 Hz, 2H), 1.78-1.68 (m, 6h), 1.25-1.21 (M, 4H), 1.11-1.09 (m, 1H). 13 C NMR (151 MHz, CDCL 3 Δ135.76, 132.27, 129.59, 128.03, 28.99, 27.79, 26.75, 22.28.

[0105] According to method C, the product 1i is a colorless oil (RF = 0.7, petroleum ether), and the yield is 66% (765 mg). Character data: 1 H NMR (400MHz, CDCL 3 Δ8.03-8.02 (m, 1H), 7.93 (D, J = 8.4 Hz, 1H), 7.87-7.86 (m, 1H), 7.82-7.80 (m, 1H), 7.61-7.60 (m, 2H) , 7.49-7.33 (m, 6H), 5.24 (S, 2H). 13 C NMR (151MHz, CDCL 3 ) δ137.37, 136.95, 135.81, 133.29, 131.57, 131.08, 131.4, 130.00, 128.98, 128.30, 128.09, 126.50, 126.00, 125.45.

Example Embodiment

[0106] Example 2

[0107] Synthesis of silanol and alcohol substrate

[0108]

[0109] Method D: NBULI (2.5 m hexane solution, 1.1 equivalents) was added dropwise to the aryl bromide (1.0 equivalend) at -78 ° C, argon (0.5 m) solution, and mixture at -78 ° C. The mixture was stirred for 1 h, and the chlorine diimethylsilane (1.2 equivalents) was added, and the mixture was stirred at -78 ° C for 1 h, then warmed to room temperature and stirred overnight. Finally, the reaction mixture is saturated at -78 ° C. 4 CL quenching, after rising to room temperature, filtrate the mixture, use ET 2 O Wash, combine organic layers, with MGSO 4 Dry, filtration, evaporation and evaporation were evaporated, and the corresponding product was obtained directly for the next step without further purification.

[0110] Method E: In the air atmosphere, add KMNO to the silane in THF (0.5 m) solution 4 (1.5 equivalents), the mixture is stirred at room temperature for 24 h, filtered through the short silica gel, with CH 2 CL 2 Wash, organic layers with MGSO 4 Dry, filtrate, evaporate under reduced pressure. The crude mixture was purified by silica gel column chromatography to give a silanol product.

[0111]

[0112] According to the method E, the product 2a is a colorless liquid (RF = 0.3, petroleum ether / ethyl acetate = 10: 1), and the yield is 94% () 722 mg). Character data: 1 H NMR (400MHz, CDCL 3 Δ7.60-7.58 (m, 2H), 7.39-7.37 (m, 3H), 1.98 (S, 1H), 0.40 (S, 6H). 13 C NMR (101MHz, CDCL 3 Δ139.27, 133.18, 129.77, 128.04, 0.11. HRMS (ESI, M / Z) Accurate Quality Calculation C 8 Hide 11 OSI [M-H - ]: 151.0585, measured value: 151.0575.

[0113] According to method D, E preparation, the product 2b is a colorless liquid (RF = 0.2, petroleum ether / ethyl acetate = 10: 1), and the two-step yield is 50% (903 mg). 1 H NMR (600MHz, CDCL 3 Δ7.51 (D, J = 8.4 Hz, 2H), 6.92 (D, J = 7.8 Hz, 2H), 3.81 (S, 3H), 2.37 (S, 1H), 0.37 (S, 6H). 3 C NMR (151MHz, CDCL 3 Δ161.00, 134.77, 130.32, 113.77, 55.20, 0.23. HRMS (ESI, M / Z) Accurate Quality Calculation C 9 Hide 13 O 2 Si [M-H - ]: 181.0690, measured value: 181.0681.

[0114] According to the method D, E preparation, the product 2c is a colorless liquid (RF = 0.2, petroleum ether / ethyl acetate = 20: 1), and the two-step yield is 30% (568 mg). Character data: 1 H NMR (600MHz, CDCL 3 Δ7.50 (D, J = 7.8 Hz, 2H), 7.35 (D, J = 7.2 Hz, 2H), 2.11 (S, 1H), 0.38 (S, 6H). 13 C NMR (101MHz, CDCL 3 Δ137.50, 136.07, 134.59, 128.27, 0.16. HRMS (ESI, M / Z) Accurate Quality Calculation C 8 Hide 10 Closi [M-H - ]: 185.0195, measured value: 185.0188.

[0115] According to methods D, E preparation, the product 2D is a colorless liquid (RF = 0.2, petroleum ether / ethyl acetate = 20: 1), and the two-step yield is 44% (752 mg). Character data: 1 H NMR (400MHz, CDCL 3 δ 7.53-7.45 (m, 1H), 7.42-7.33 (m, 1H), 7.03-6.97 (m, 1H), 2.05 (S, 1H), 0.45 (S, 6h). 13 C NMR (151MHz, CDCL 3 ) δ167.03 (d, j CF = 241.4 Hz), 135.20 (D, J CF = 11.0 Hz), 131.81 (D, J CF = 8.4Hz), 125.73 (D, J CF = 29.8Hz), 123.93 (D, J CF = 2.8Hz), 114.81 (D, J CF = 25.7 Hz), 1.44. 19 F NMR (565MHz, CDCL 3 Δ-101.15. HRMS (ESI, M / Z) Accurate Quality Calculation C 8 Hide 12 FOSI [M + H + ]: 171.0636, measured value: 171.0627.

[0116] According to method E, the product 2e is a colorless liquid (RF = 0.3, petroleum ether / ethyl acetate = 10: 1), the yield is 53% (565 mg). Character data: 1 H NMR (400MHz, CDCL 3 Δ7.60-7.58 (m, 4H), 7.40-7.34 (m, 6H), 2.48 (S, 1H), 0.65 (S, 3H). 13 C NMR (151MHz, CDCL 3 Δ137.21, 134.10, 130.02, 128.05, -1.13. HRMS (ESI, M / Z) Accurate Quality Calculation C 13 Hide 13 OSI [M-H - ]: 213.0741, measured value: 213.0736.

[0117]

[0118] 2F is prepared according to the reference [Angew.Chem.int.ed.2018, 57, 11952-11956]. Purge KOH (1.12g, 20.0 mmol) by argon 2 O / methanol (20 mL, 1/4, v / v) solution, then add tert-butyl chlorphenylsilane (5.0 g, 18.2 mmol) of ET purged with argon 2 O (30 mL) solution, the resulting mixture was stirred at room temperature for 24 h. Different water layer, use ET 2 O Extraction, combined ether with MgSO 4 The evaporation was dried and evaporated, the clear oil was obtained, and the white solid was allowed to be a white solid, which was tert-butyldiphenylsilyl alcohol (1.54 g, 33% yield). Character data: 1 H NMR (400MHz, CDCL 3 Δ7.71 (DD, J = 7.0, 0.7 Hz, 4H), 7.41-7.35 (M, 6H), 2.17 (S, 1H), 1.07 (S, 9H). 13 C NMR (101 MHz, CDCL 3 Δ135.31, 134.95, 129.80, 127.87, 26.70, 19.15.

[0119] 2G was prepared according to the reference [ACS Appl.mater.interfaces.2012, 4, 5813-5820.]. Phenothiazine (2.0 g, 10.0 mmol) and 2-bromoethanol (0.71 mL, 10.0 mmol), suspension were added to the ice bath cooled NaH (60% mineral oil, 600 mg, 25 mmol) DMF (15 mL) suspension. At room temperature, stirring was stirred under nitrogen for 5 h. The mixture was cooled to room temperature and brine, and the organic phase was collected with dichloromethane, and used Na. 2 SO 4 After drying, after evaporation of the solvent, the crude compound was purified by silica gel column chromatography to give the desired product (1.12 g, 46% yield). Character data: 1 H NMR (400MHz, CDCL 3: δ 7.19-7.14 (m, 4H), 6.97-6.89 (m, 4H), 4.09 (T, J = 5.2 Hz, 2H), 3.20 (T, J = 5.2 Hz, 2H), 2.20 (s, 1h). 13 C NMR (101MHz, CDCL 3 Δ145.19, 127.85, 127.51, 126.30, 123.14, 115.98, 58.80, 49.68.

[0120] 2 h was prepared according to the reference [Langmuir.2008, 24, 5140-5145]. Under 0 ° C, NBULI (2.5 m-hexane solution, 2.2 equivalents, 8.8 ml of 20 ml 3: 1 benzene / ether) was added to 1,6-dibromobrene (1.8 g, 5.0 mmol, 20 ml 3: 1 benzene). The yellow mixture was refluxed at 60 ° C for 2.0 h, and the mixture was cooled to room temperature, and 1.7 g was added to formaldehyde in 10 ml of diethyl ether, the resulting solution was heated to reflux 3.0 h, then cooled to room temperature, filtrate removal of light orange solid, water with water The solid was washed with dilute hydrochloric acid, dried under vacuum (832 mg, 63% yield). Character data: 1 H NMR (600MHz, DMSO-D 6 Δ8.34 (D, J = 9.6 Hz, 2H), 8.27 (D, J = 7.8 Hz, 2H), 8.19 (D, J = 9.0 Hz, 2H), 8.14 (D, J = 7.8 Hz, 2H) , 5.25 (s, 4h). 13 C NMR (151MHz, DMSO-D 6 Δ135.96, 129.70, 127.89, 127.30, 125.54, 124.64, 124.15, 122.87, 61.41.

Example Embodiment

[0121] Example 3

[0122] NETATISTRY: Dihydrosilane and silanols Screening:

[0123] In the presence of a RH catalyst, the tert-butyl (4-methoxyphenyl) silane 1A was carried out by the dimethyl (phenyl) silanol 2a, and the molecular dehydrogenated Si-O reacted reaction was carried out at room temperature, toluene solvent, Try several chiral phosphine ligands, using [RH (COD) Cl] 2 (1 mol%) As the catalyst and JosiPHOS L1 (2.2 mol%) as a chiral ligand, the silicone product 3a is successfully obtained, the yield is 36%, the enantiomer is good (EE is 74%), and other electrons have different electrons Features Josiphos-type ligands (L2 and L3) are also feasible ligands.

[0124] The JosiPhos ligand L4, yield, and no-selectivity of the substituent using the phosphorus atom (68% yield, 97% EE) were significantly increased. Further screening of the counterpart ligand found that BinaP L5 and Segphos L6 also valid for the reaction.

[0125] Using L4 ligands, common solvent DCE (1,2-dichloroethane) and 1,4-dioxane will reduce yields.

[0126]

[0127]

[0128]

[0129] Reaction conditions: In an argon atmosphere, in a 2.0 mL solvent, 1a (0.24 mmol), 2a (0.2 mmol), [RH (COD) Cl] 2 (1 mol%), ligand (2.2mol%), reaction 12 hours; use CH 2 Br 2 As the internal standard, pass 1 H NMR measurement yield; EE value is determined by chiral HPLC.

[0130] The product is a colorless oil (RF = 0.5, petroleum ether). Analysis by Daicel ChiralPak OD-3 column (n-hexane, 0.6 mL / min), λ = 210 nm, temperature = 28 ° C, T r (minor) = 9.3min, T r (Major) = 9.7 min. Number of identity: [α] D 23.0 = -28.0 (C = 1.0, CHCL 3 ). 1 H NMR (600MHz, CDCL 3 Δ7.55 (D, J = 6.6 Hz, 2H), 7.47 (D, J = 7.8 Hz, 2H), 7.37-7.33 (M, 3H), 6.89 (D, J = 8.4 Hz, 2H), 4.77 ( S, 1H), 3.81 (S, 3H), 0.90 (S, 9H), 0.35 (S, 6H). 13 C NMR (151MHz, CDCL 3 Δ161.06, 139.59, 135.75, 133.19, 129.45, 127.85, 126.46, 113.50, 55.12, 25.53, 18.37, 0.70. HRMS (ESI, M / Z) Accurate Quality Calculation C 19 Hide 29 O 2 Si 2 [M + h + ]: 345.1701, measured value: 345.1701.

[0131] After obtaining the optimum reaction conditions, silicon chiral silicone silicone is constructed with this method, with a benzene ring, a naphthalene ring, a naphthalene ring, an electron with a metalloxy, morphine group, and an electron-propelled fluorine. Both of which are reacted with dimethyl (phenyl) silanol 2a, with medium to good yield (54 to 98%), excellent enantios selectivity (96 to 98% EE) to obtain a corresponding product. Then, the application of silanol is expanded, and the base of the dimethylphenylsilyl silanol has good tolerance, and the product is obtained from 89 to 97% EE. Methyl diylsilyl alcohol, tert-butyldiphenylsilyl alcohol and trimethylsilyl alcohol are also feasible substrates, which are produced at 56 to 75% yield, and the selectivity (93 ~ 97%) is not decline. The silane diol is double coupled to the dihydrogen, and two silicon-chiral silanes can be constructed. The TBU is replaced with methyl, isopropyl, cyclohexyl or 1-naphthyl, smoothly obtained product, EE is 63 to 88%.

[0132]

[0133] Step f: In the glove box, add [RH (COD) Cl] to 10ml vials [RH (COD) Cl] 2 (1.0 mg, 1 mol%), L4 (2.4 mg, 2.2 mol%), toluene (2 mL), dihydrosilane substrate (0.24 mmol, 1.2 equivalents), silanol substrate (0.2 mmol, 1.0 equivalents). The reaction tube was covered and then removed from the glove box and stirred at room temperature overnight. After the reaction is completed, the reaction mixture is filtered through a short silica product and evaporated under reduced pressure, purified by preparing TLC to obtain a target product. The enantiomer is determined by chiral HPLC analysis, and the corresponding circumference is obtained as a reference in the same conditions and (±) -binap or (±) -L4).

[0134] Step G: oxidation of chiral silane products. Add urea / hydrogen peroxide mixtures (UHP, 1.0 equivalents) to methyl trioxide (MTO, 10 mol%), and the resulting mixture was stirred for 10 min, then the silane substrate (1.0 equivalent) was added. . After stirring at ambient temperature overnight, the mixture was filtered through a short silica layer, and then the crude product was purified by preparing TLC to obtain a target product.

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Classification and recommendation of technical efficacy words

Increase variety
High correspondence selectivity

Silicon-center chiral silicon-oxygen compound and preparation method thereof

AI-Extracted Technical Summary

Problems solved by technology

Method used

Abstract

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Examples

Example Embodiment

Example Embodiment

Example Embodiment

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Description & Claims & Application Information

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