CN109796492A - A kind of preparation method of the phosphorus nitrence compound of cadmium sulfide catalysis - Google Patents
A kind of preparation method of the phosphorus nitrence compound of cadmium sulfide catalysis Download PDFInfo
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- CN109796492A CN109796492A CN201910042642.0A CN201910042642A CN109796492A CN 109796492 A CN109796492 A CN 109796492A CN 201910042642 A CN201910042642 A CN 201910042642A CN 109796492 A CN109796492 A CN 109796492A
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Abstract
The invention belongs to medicine and native compound chemical intermediate and related chemistry technical fields, are related to a kind of preparation method of the phosphorus nitrence compound of cadmium sulfide catalysis.The present invention is with phosphine compound and 3- substitution-Isosorbide-5-Nitrae, and 2- dioxazole -5- ketone is raw material, and using cadmium sulfide as catalyst, under illumination condition, a step constructs phosphorus nitrence compound.Wherein 3- substitution-Isosorbide-5-Nitrae, the molar concentration of 2- dioxazole -5- ketone compound in a solvent are 0.01~2mmol/mL, and the molar ratio with used catalyst is 1:0.01~1:0.5.The beneficial effects of the invention are as follows the reactions to use light-catalyzed reaction, and cleanliness without any pollution, reaction condition is mild, and operation and post-processing are simple, substrate good compatibility.
Description
Technical field
The invention belongs to medicine and native compound chemical intermediate and related chemistry technical fields, are related to a kind of cadmium sulfide
The preparation method of the phosphorus nitrence compound of catalysis.
Background technique
Sunlight is the prerequisite of human survival, and it is cheap and easily-available, cleaning is renewable, it is considered to be optimal energy
Source.Photocatalysis is the mild synthetic technology of a kind of cleanliness without any pollution, reaction condition, is usually avoided that some Strong oxdiative go back original reagents
Or the use of other noxious materials, it largely can satisfy requirement of the people to the energy and environment.
Analog of the phosphorus nitrence as phosphorus ylide can use lone pair electrons and transition-metal coordination on nitrogen, coordination
Obtained metal complex can be catalyzed many homogeneous reactions as catalyst, and hydrogenation including metal catalytic turns metal
Change reaction, carbon carbon coupling reaction, olefinic polymerization, cyclopropyl olefination, Meyer-Schuster rearrangement, allyl group alkylated, oxygen
Change reaction and hydroisomerization.
The method of conventional synthesis phosphorus nitrence is mainly staudinger reaction: aziminobenzene compound and triphenylphosphine it is anti-
It answers, this reaction has quantitatively obtained a new compound phosphorus nitrence (azepine ylide either phosphine imide), and releases
One molecule nitrogen [referring to Garcia-Alvarez, J., Garcia-Garrido, S.E., Cadierno,
V.J.Organomet.Chem., 2014,751,792.], although this method reaction speed is fast, substrate spectrum is wider, exist
The disadvantages of multistep reaction gross production rate is low, raw material and intermediate are unstable.Other synthetic methods there is also gross production rates low, substrate
The disadvantages of scope of application is small [referring to: (a) Tamura Y, Minamikawa J, Haruki S, et al.Synthesis, 1974,
1974,361.(b)Yavari I,Zabarjad-Shiraz N.Mol.Diversity,2006,10,23.(c)Armstrong
A,Jones L H,Knight J D,et al.Org.Lett.,2005,7,713.(d)Cristau H J,Hammami A,
Torreilles E.Heteroat.Chem.,1999,10,49.]。
Summary of the invention
The present invention provides a kind of preparation method of phosphorus nitrence, higher yields are can be obtained in this method in a mild condition,
It is not necessary that extra ligand, substrate good compatibility is added.
Technical solution of the present invention:
A kind of preparation method of the phosphorus nitrence compound of cadmium sulfide catalysis, this method with phosphine compound and 3- substitution-Isosorbide-5-Nitrae,
2- dioxazole -5- ketone is raw material, using cadmium sulfide as catalyst, under illumination condition, and one-step synthesis phosphorus nitrence compound, synthesis
Route is as follows:
In formula: R1Selected from one of alkyl, aryl；R2Selected from one of aryl, alkoxy.
The molar ratio of 3- substitution -1,4,2- dioxazole -5- ketone and cadmium sulfide is 1:0.01~1:1.0.
Organic solvent in synthetic reaction is ether, acetonitrile, dimethyl sulfoxide, dioxane, tetrahydrofuran, toluene, first
One or more of alcohol, ethyl alcohol, chloroform, methylene chloride, dichloroethanes, acetone, N,N-dimethylformamide are mixed
It closes.The molar concentration of 3- substitution -1,4,2- dioxazole -5- ketone in organic solvent is 0.01~2mmol/mL.
The molar ratio of 3- substitution -1,4,2- dioxazole -5- ketone and phosphine compound is 1:1.0~1:6.0.
Synthesis reaction temperature is 10 DEG C~100 DEG C, and synthesising reacting time is 1h~36h.
The power of illumination is 1W~36W；Illumination wavelength is wave band some or all of in 280nm~600nm.
Beneficial effects of the present invention: the reaction use light-catalyzed reaction, cleanliness without any pollution, reaction condition is mild, operation and
Post-processing is simple, substrate good compatibility.
Detailed description of the invention
Fig. 1 is N- (triphenyl-λ in embodiment 15Phosphine subunit) benzamide1H nuclear magnetic spectrogram.
Fig. 2 is N- (triphenyl-λ in embodiment 25Phosphine subunit) 4- methyl benzamide1H nuclear magnetic spectrogram.
Fig. 3 is N- (triphenyl-λ in embodiment 35Phosphine subunit) 3- methoxybenzene amide1H nuclear magnetic spectrogram.
Fig. 4 is N- (triphenyl-λ in embodiment 45Phosphine subunit) 4- methoxybenzene amide1H nuclear magnetic spectrogram.
Fig. 5 is N- (triphenyl-λ in embodiment 55Phosphine subunit) 4- bromobenzene amide1H nuclear magnetic spectrogram.
Fig. 6 is N- (triphenyl-λ in embodiment 65Phosphine subunit) 4- trifluoromethyl benzamide1H nuclear magnetic spectrogram.
Fig. 7 is N- (triphenyl-λ in embodiment 75Phosphine subunit) 2- fluorobenzene amide1H nuclear magnetic spectrogram.
Fig. 8 is N- (triphenyl-λ in embodiment 85Phosphine subunit) 2- amide1H nuclear magnetic spectrogram.
Fig. 9 is N- (triphenyl-λ in embodiment 95Phosphine subunit) formamide1H nuclear magnetic spectrogram.
Figure 10 is [three (4- the aminomethyl phenyl)-λ of N- in embodiment 105Phosphine subunit] benzamide1H nuclear magnetic spectrogram.
Figure 11 is N- [triethoxy-λ in embodiment 115Phosphine subunit] benzamide1H nuclear magnetic spectrogram.
Specific embodiment
Present invention will be further explained below with reference to specific examples.Technical staff in the art is the present invention
Simple replacement or improvement belong within the technical solution protected of the present invention.
Embodiment 1:N- (triphenyl-λ5Phosphine subunit) benzamide synthesis
Accurately weigh 3- phenyl-Isosorbide-5-Nitrae, 2- dioxazole -5- ketone (48.9mg, 0.3mmol), triphenylphosphine (157.2mg,
0.6mmol), cadmium sulfide (2.2mg, 5mol%) is added in the Schlenk reaction flask of 25mL, and toluene (2mL) then is added, sets
In the lower 10 DEG C of reactions 36h of illumination condition (1W, 280nm).After reaction, solvent is removed under reduced pressure, uses petrol ether/ethyl acetate
As eluant, eluent, silica gel post separation, the yield of product is 95%.
1H NMR(400MHz,CDCl3)δ8.40-8.35(m,2H),7.90-7.81(m,6H),7.60-7.53(m,3H),
7.52-7.37(m,9H).
Embodiment 2:N- (triphenyl-λ5Phosphine subunit) 4- methyl benzamide synthesis
Accurately weigh 3- (4- aminomethyl phenyl)-Isosorbide-5-Nitrae, 2- dioxazole -5- ketone (53.1mg, 0.3mmol), triphenylphosphine
(78.6mg, 0.3mmol), cadmium sulfide (0.4mg, 1mol%) are added in the Schlenk reaction flask of 25mL, and dichloro is then added
Methane (2mL) is placed in the lower 20 DEG C of reactions of illumination condition (15W, 420nm) for 24 hours.After reaction, solvent is removed under reduced pressure, uses stone
Oily ether/ethyl acetate is 91% as eluant, eluent, silica gel post separation, the yield of product.
1H NMR(400MHz,CDCl3) δ 8.28 (d, J=8.0Hz, 2H), 7.92-7.81 (m, 6H), 7.59-7.52 (m,
3H), 7.51-7.42 (m, 6H), 7.22 (d, J=8.0Hz, 2H), 2.40 (s, 3H)
Embodiment 3:N- (triphenyl-λ5Phosphine subunit) 3- methoxybenzene amide synthesis
Accurately weigh 3- (3- methoxyphenyl)-Isosorbide-5-Nitrae, 2- dioxazole -5- ketone (57.9mg, 0.3mmol), triphenylphosphine
(157.2mg, 0.6mmol), cadmium sulfide (21.7mg, 50mol%) are added in the Schlenk reaction flask of 50mL, are then added
Dichloroethanes (30mL) is placed in the lower 20 DEG C of reactions 8h of illumination condition (25W, 450nm).After reaction, solvent is removed under reduced pressure, makes
Use petrol ether/ethyl acetate as eluant, eluent, silica gel post separation, the yield of product is 90%.
1H NMR(400MHz,CDCl3)δ8.06-8.00(m,1H),7.91-7.80(m,7H),7.58-7.52(m,3H),
7.51-7.45(m,6H),7.36-7.29(m,1H),7.04-6.99(m,1H),3.85(s,3H).
Embodiment 4:N- (triphenyl-λ5Phosphine subunit) 4- methoxybenzene amide synthesis
Accurately weigh 3- (4- methoxyphenyl)-Isosorbide-5-Nitrae, 2- dioxazole -5- ketone (57.9mg, 0.3mmol), triphenylphosphine
(131mg, 0.5mmol), cadmium sulfide (4.3mg, 10mol%) are added in the Schlenk reaction flask of 25mL, and toluene is then added
(1.5mL) is placed in the lower 30 DEG C of reactions 10h of illumination condition (10W, 600nm).After reaction, solvent is removed under reduced pressure, uses petroleum
Ether/ethyl acetate is 87% as eluant, eluent, silica gel post separation, the yield of product.
1H NMR(400MHz,CDCl3)δ8.35-8.31(m,2H),7.89-7.80(m,6H),7.58-7.51(m,3H),
7.50-7.43 (m, 6H), 6.91 (d, J=8.8Hz, 2H), 3.83 (s, 3H)
Embodiment 5:N- (triphenyl-λ5Phosphine subunit) 4- bromobenzene amide synthesis
Accurately weigh 3- (4- bromophenyl)-Isosorbide-5-Nitrae, 2- dioxazole -5- ketone (72.6mg, 0.3mmol), triphenylphosphine
(157.2mg, 0.6mmol), cadmium sulfide (8.7mg, 20mol%) are added in the Schlenk reaction flask of 25mL, are then added two
Six ring of oxygen (2mL) is placed in the lower 40 DEG C of reactions 10h of illumination condition (36W, 500nm).After reaction, solvent is removed under reduced pressure, uses
Petrol ether/ethyl acetate is 85% as eluant, eluent, silica gel post separation, the yield of product.
1H NMR(400MHz,CDCl3)δ8.26-8.20(m,2H),7.88-7.78(m,6H),7.60-7.52(m,4H),
7.52-7.44(m,7H).
Embodiment 6:N- (triphenyl-λ5Phosphine subunit) 4- trifluoromethyl benzamide synthesis
Accurately weigh 3- (4- trifluoromethyl)-Isosorbide-5-Nitrae, 2- dioxazole -5- ketone (69.3mg, 0.3mmol), triphenylphosphine
(131mg, 0.5mmol), cadmium sulfide (43.3mg, 100mol%) are added in the Schlenk reaction flask of 25mL, and first is then added
Benzene (2mL), methylene chloride (2mL) are placed in the lower 40 DEG C of reactions 8h of illumination condition (5W, 350nm).After reaction, it is removed under reduced pressure
Solvent uses petrol ether/ethyl acetate as eluant, eluent, and silica gel post separation, the yield of product is 96%.
1H NMR(400MHz,CDCl3) δ 8.45 (d, J=8.0Hz, 2H), 7.89-7.80 (m, 6H), 7.66 (d, J=
8.4Hz,2H),7.63-7.55(m,3H),7.54-7.46(m,6H).
Embodiment 7:N- (triphenyl-λ5Phosphine subunit) 2- fluorobenzene amide synthesis
Accurately weigh 3- (2- fluorophenyl)-Isosorbide-5-Nitrae, 2- dioxazole -5- ketone (54.3mg, 0.3mmol), triphenylphosphine
(157.2mg, 0.6mmol), cadmium sulfide (4.3mg, 10mol%) are added in the Schlenk reaction flask of 25mL, are then added two
Chloromethanes (2mL) is placed in the lower 60 DEG C of reactions 8h of illumination condition (25W, 550nm).After reaction, solvent is removed under reduced pressure, uses
Petrol ether/ethyl acetate is 85% as eluant, eluent, silica gel post separation, the yield of product.
1H NMR(400MHz,CDCl3)δ8.19-8.12(m,1H),7.89-7.81(m,6H),7.59-7.52(m,3H),
7.51-7.44(m,6H),7.39-7.32(m,1H),7.16-7.10(m,1H),7.10-7.03(m,1H),.
Embodiment 8:N- (triphenyl-λ5Phosphine subunit) 2- amide synthesis
Accurately weigh 3- (2- furyl)-Isosorbide-5-Nitrae, 2- dioxazole -5- ketone (45.9mg, 0.3mmol), triphenylphosphine
(131mg, 0.5mmol), cadmium sulfide (4.3mg, 10mol%) are added in the Schlenk reaction flask of 25mL, and toluene is then added
(2mL) is placed in the lower 10 DEG C of reactions 20h of illumination condition (10W, 280-600nm).After reaction, solvent is removed under reduced pressure, uses stone
Oily ether/ethyl acetate is 83% as eluant, eluent, silica gel post separation, the yield of product.
1H NMR(400MHz,CDCl3) δ 7.88-8.81 (m, 6H), 7.78 (d, J=2.4Hz, 1H), 7.60-7.53 (m,
3H), 7.51-7.45 (m, 6H), 7.37 (d, J=3.6Hz, 1H), 7.07-7.02 (m, 1H)
Embodiment 9:N- (triphenyl-λ5Phosphine subunit) formamide synthesis
Accurately weigh 3- methyl-1,4,2- dioxazole -5- ketone (30.3mg, 0.3mmol), triphenylphosphine (104.8mg,
0.4mmol), cadmium sulfide (4.3mg, 10mol%) is added in the Schlenk reaction flask of 25mL, and methylene chloride is then added
(2mL) is placed in the lower 50 DEG C of reactions 5h of illumination condition (36W, 450nm).After reaction, solvent is removed under reduced pressure, using petroleum ether/
Ethyl acetate is 89% as eluant, eluent, silica gel post separation, the yield of product.
1H NMR(400MHz,CDCl3)δ7.78-7.66(m,6H),7.57-7.48(m,3H),7.47-7.38(m,6H),
2.23 (d, J=2.8Hz, 3H)
Embodiment 10:N- [three (4- aminomethyl phenyl)-λ5Phosphine subunit] benzamide synthesis
Accurately weigh 3- phenyl-Isosorbide-5-Nitrae, 2- dioxazole -5- ketone (48.9mg, 0.3mmol), three (p-methylphenyl) phosphines
(121.7mg, 0.4mmol), cadmium sulfide (4.3mg, 10mol%) are added in the Schlenk reaction flask of 25mL, and first is then added
Benzene (2mL) is placed in the lower 100 DEG C of reactions 1h of illumination condition (10W, 480nm).After reaction, solvent is removed under reduced pressure, uses petroleum
Ether/ethyl acetate is 94% as eluant, eluent, silica gel post separation, the yield of product.
1H NMR(400MHz,CDCl3) δ 8.25 (d, J=7.2Hz, 2H), 7.68-7.57 (m, 6H), 7.34-7.25 (m,
3H),7.21-7.12(m,6H),2.29(s,9H).
Embodiment 11:N- [triethoxy-λ5Phosphine subunit] benzamide synthesis
Accurately weigh 3- phenyl-Isosorbide-5-Nitrae, 2- dioxazole -5- ketone (48.9mg, 0.3mmol), triethoxy phosphine (66.5mg,
0.4mmol), cadmium sulfide (4.3mg, 10mol%) is added in the Schlenk reaction flask of 25mL, and toluene (2mL) then is added,
It is placed in the lower 100 DEG C of reactions 1h of illumination condition (10W, 480nm).After reaction, solvent is removed under reduced pressure, uses petroleum ether/acetic acid
Ethyl ester is 88% as eluant, eluent, silica gel post separation, the yield of product.
1H NMR(400MHz,CDCl3) δ 8.17 (d, J=7.6Hz, 2H), 7.48-7.41 (m, 1H), 7.40-7.31 (m,
2H), 4.36-4.21 (m, 6H), 1.38 (t, J=7Hz, 9H).
Claims (10)
1. a kind of preparation method of the phosphorus nitrence compound of cadmium sulfide catalysis, which is characterized in that this method is with phosphine compound and 3-
Substitution-Isosorbide-5-Nitrae, 2- dioxazole -5- ketone is raw material, using cadmium sulfide as catalyst, under illumination condition, and one-step synthesis phosphorus nitrence
Object is closed, synthetic route is as follows:
In formula: R1Selected from one of alkyl, aryl；R2Selected from one of aryl, alkoxy.
2. preparation method according to claim 1, which is characterized in that 3- substitution-Isosorbide-5-Nitrae, 2- dioxazole -5- ketone and cadmium sulfide
Molar ratio be 1:0.01~1:1.0.
3. preparation method according to claim 1 or 2, which is characterized in that the organic solvent in synthetic reaction is ether, second
Nitrile, dimethyl sulfoxide, dioxane, tetrahydrofuran, toluene, methanol, ethyl alcohol, chloroform, methylene chloride, dichloroethanes, third
The mixing of one or more of ketone, N,N-dimethylformamide；3- substitution -1,4,2- dioxazole -5- ketone is in organic solvent
In molar concentration be 0.01~2mmol/mL.
4. preparation method according to claim 1 or 2, which is characterized in that 3- substitution-Isosorbide-5-Nitrae, 2- dioxazole -5- ketone and phosphine
The molar ratio of compound is 1:1.0~1:6.0.
5. preparation method according to claim 3, which is characterized in that 3- substitution-Isosorbide-5-Nitrae, 2- dioxazole -5- ketone and phosphine chemical combination
The molar ratio of object is 1:1.0~1:6.0.
6. according to claim 1, preparation method described in 2 or 5, which is characterized in that synthesis reaction temperature is 10 DEG C~100 DEG C,
Synthesising reacting time is 1h~36h.
7. preparation method according to claim 3, which is characterized in that synthesis reaction temperature is 10 DEG C~100 DEG C, and synthesis is anti-
It is 1h~36h between seasonable.
8. the preparation method according to claim 4, which is characterized in that synthesis reaction temperature is 10 DEG C~100 DEG C, and synthesis is anti-
It is 1h~36h between seasonable.
9. according to claim 1, preparation method described in 2,5,7 or 8, which is characterized in that the power of illumination is 1W~36W；Light
It is wave band some or all of in 280nm~600nm according to wavelength.
10. preparation method according to claim 6, which is characterized in that the power of illumination is 1W~36W；Illumination wavelength is
Wave band some or all of in 280nm~600nm.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112142792A (en) * | 2020-09-16 | 2020-12-29 | 大连理工大学 | Novel method for constructing nitrogen-phosphorus double bonds through visible light catalysis |
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| CN1299820A (en) * | 2000-12-19 | 2001-06-20 | 中国科学院上海有机化学研究所 | Ferrocene oxazoline phosphino ligand with several chiral centers and its synthesis and use |
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2019
- 2019-01-17 CN CN201910042642.0A patent/CN109796492A/en not_active Withdrawn
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN1299820A (en) * | 2000-12-19 | 2001-06-20 | 中国科学院上海有机化学研究所 | Ferrocene oxazoline phosphino ligand with several chiral centers and its synthesis and use |
Non-Patent Citations (4)
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| HIROYUKI M. ET AL: ""Generation of Nitrene by the Photolysis of N-Substituted Iminodibenzothiophene"", 《J. ORG. CHEM》 * |
| RAVI K. ET AL: ""Unprecedented Transformation of a Directing Group Generated in Situ and Its Application in the One-Pot Synthesis of 2-Alkenyl Benzonitriles"", 《CHEM. EUR.J》 * |
| SERGEI A S. ET AL: ""Dehydration of Amides to Nitriles under Conditions of a Catalytic Appel Reaction"", 《ORG. LETT》 * |
| VINCENT B. ET AL: ""Light-Induced Ruthenium-Catalyzed Nitrene Transfer Reactions: A Photochemical Approach towards N-Acyl Sulfimides and Sulfoximines"", 《ANGEW. CHEM. INT. ED》 * |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN112142792A (en) * | 2020-09-16 | 2020-12-29 | 大连理工大学 | Novel method for constructing nitrogen-phosphorus double bonds through visible light catalysis |
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