CN107501309B - A kind of condensate Schiff base rare-earth ytterbium iodide and its preparation method and application - Google Patents

A kind of condensate Schiff base rare-earth ytterbium iodide and its preparation method and application Download PDF

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CN107501309B
CN107501309B CN201710780366.9A CN201710780366A CN107501309B CN 107501309 B CN107501309 B CN 107501309B CN 201710780366 A CN201710780366 A CN 201710780366A CN 107501309 B CN107501309 B CN 107501309B
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bis
phenyl
benzhydryl
oxygen
isopropyls
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CN107501309A (en
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马猛涛
王未凡
姚薇薇
徐莉
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Nanjing Forestry University
Nanjing University of Chinese Medicine
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Nanjing University of Chinese Medicine
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Abstract

The invention discloses a kind of condensate Schiff base rare-earth ytterbium iodide and its preparation method and application.The condensate Schiff base rare-earth ytterbium iodide are N (4 isopropyls 2,6 two（Benzhydryl）Phenyl) 3,5 di-t-butyl, 2 oxygen condensate Schiff base rare-earth ytterbium iodide, preparation method is：Under the conditions of anhydrous and oxygen-free, N (4 isopropyls 2,6 two（Benzhydryl）Phenyl) 3,5 di-t-butyl 2 hydroxy benzaldehyde imines and hydrofining corresponding sylvite is obtained by the reaction, then reacted with iodate ytterbium, obtain yellow crystals, as N (4 isopropyls 2,6 two（Benzhydryl）Phenyl) 3,5 di-t-butyl, 2 oxygen condensate Schiff base rare-earth ytterbium iodide.The synthesis of the condensate Schiff base rare-earth ytterbium iodide of the present invention is simple, and separating-purifying is convenient, and structure is clear, and high income；It is high as the activity that catalyst aldehyde or ketone are reacted with pinacol borine, and substrate universality is wide.

Description

A kind of condensate Schiff base rare-earth ytterbium iodide and its preparation method and application
Technical field
The present invention relates to metallo-organic compound preparing technical fields, and in particular to a kind of condensate Schiff base rare-earth ytterbium iodide and It is prepared and application.
Background technology
Hydroboration is hydrogen migration on borane reagent to being added in unsaturated organic compound, different is had to generate The reaction of machine boron compound.Hydroboration is widely used in the production of fine chemistry industry, the synthesis of material and macromolecular composite wood The preparation etc. of material.One of most important reaction is the hydroboration of carbonyls in hydroboration.Hydroboration is typically by boron Alkane reagent equimolar, which is added in carbonyls, forms borate, be then easily hydrolyzed into alcohol [Chong.C.C, Kinjo.R,ACS Catal.2015,5,3238-3259；Geier.S.J,Vogels.C.M,Westcott.S.A,ACS Symp.Ser.2016,1236,209-225].Metallic catalyst is due to its excellent catalytic effect, and by-product is few and safety and environmental protection etc. is excellent Point, a series of different metallic catalysts are reported out.Commonly magnesium-yttrium-transition metal compound carrys out catalysis of carbonyl chemical combination object Hydroboration [Vasilenko.V, Blasius.C.K, Wadepohl.H, Gade.L.H, Angew.Chem.Int.Ed.2017, 56,8393-8397；Eedugurala.N,Wang.Z,Chaudhary.U,Nelson.N,Kandel.K,Kobayashi.T, Slowing.I.I,Pruski.M,Sadow.A.D,ACS Catal.2015,5,7399-7414；Guo.J,Chen.J,Lu.Z, Chem.Commun.2015,51,5725-5727].Such as the discoveries such as Gade contain the manganese Metal of chiral " boxmi " pincer ligand Alkyl compound is as catalyst, many useful alcohol with chirality of synthesis；Lu et al. is synthesized using iminopyridine ligand Cobalt metal compound is catalyzed the hydroboration of aryl ketones and pinacol borine, obtains preferable effect.It is anti-in hydroboration catalysis Answer middle main group metal it is of increased attention in recent years [Mukherjee.D, Osseili.H, Spaniol.T.P, Okuda.J,J.Am.Chem.Soc.2016,138,10790-10793；Arrowsmith.M,Hadlington.T.J, Hill.M.S,Ko A,G,Chem.Commun.2012,48,4567–4569；Yadav.S,Pahar.S, Sen.S.S,Chem.Commun.2017,53,4562-4564；Hadlington.T.J,Hermann.M,Frenking.G, Jones.C,J.Am.Chem.Soc.2014,136,3028-3031].In 2nd main group alkaline-earth metal, Hill etc. has been prepared for The butyl of beta-diimine magnesium has successfully been catalyzed the boron of a variety of aromatic series and aliphatic aldehyde and ketone under mild conditions Hydrogenation.In 13 race's elements, Nembenna etc. is recently reported the hydride of the five-membered ring aluminium containing N, as efficient catalysis Agent, has been catalyzed a variety of different aldehyde and ketone, yield are higher.Then, in the 1st major element alkali metal, Okuda etc. reports triphen The hydroboration of base boron alkali metal salt catalysis of carbonyl chemical combination object, efficiency are very high.
The prior art indicate that the example using rare earth metal is less, see [Dudnik.A.S, Weidner.V.L, Motta.A,Delferro.M,Marks.T.J,Nat.Chem.2014,6,1100-1107；Weidner.V.L, Barger.C.J,Delferro.M,Lohr.T.L,Marks.T.J,ACS Catal.2017,7,1244-1247；Chen.S, Yan.D,Xue.M,Hong.Y,Yao.Y,Shen.Q,Org.Lett.2017,19,3382-3385].At present only two about The hydroboration of catalysis of rare-earth compound aldehyde and ketone is reported.One is the La [N reported in 2017 by Lohr etc. (SiMe3)2], it is selectively catalyzed the hydroboration of different ketone and aldehyde at room temperature.Another kind is that Shen etc. reports a system Row rare earth compound Cp3Ln (Ln=Y, Yb, Sm, Nd and La), has efficiently been catalyzed the hydroboration of aldehyde and ketone.Schiff bases heavy rare earth Metallic compound and its hydroboration of catalysis aldehyde and ketone there is no report so far.
Invention content
Goal of the invention：For the deficiencies in the prior art, the object of the present invention is to provide one kind with schiff bases be with The rare earth ytterbium iodide of body.It is a further object of the present invention to provide above-mentioned using schiff bases as the preparation side of the ytterbium iodide of ligand Method.Further object of the present invention is to provide a kind of above-mentioned using schiff bases as the application of the ytterbium iodide of ligand.
Technical solution：For achieving the above object, the technical solution adopted by the present invention is：
A kind of condensate Schiff base rare-earth ytterbium iodide are：Bis- uncles of N- (4- isopropyls -2,6- bis- (benzhydryl) phenyl) -3,5- Butyl -2- oxygen condensate Schiff base rare-earth ytterbium iodide, structural formula are as follows：
A kind of preparation method of the condensate Schiff base rare-earth ytterbium iodide, includes the following steps：
(1) under the conditions of anhydrous and oxygen-free, in single port reaction tube, by N- (4- isopropyls -2,6- bis- (benzhydryl) phenyl) -3, 5- di-t-butyls-Benzaldehyde,2-hydroxy imines is dissolved in tetrahydrofuran solution, -80--40 DEG C, the tetrahydrofuran solution of hydrofining Above-mentioned solution is added dropwise, reacts at room temperature 2-4h；Obtain bis- uncles of N- (4- isopropyls -2,6- bis- (benzhydryl) phenyl) -3,5- Butyl -2- oxygen schiff bases sylvite；Wherein, N- (4- isopropyls -2,6- bis- (benzhydryl) phenyl) -3,5- di-t-butyl -2- hydroxyls Benzaldehyde imines, hydrofining molar ratio be 1: 1-1.5；Its reaction equation is as follows：
(2) under the conditions of anhydrous and oxygen-free, in single port reaction tube, triiodide ytterbium, which is dissolved in tetrahydrochysene, barks and mutters, -80--40 DEG C, dropwise plus Enter step (1) described solution, react 10-20h, solvent is drained, and toluene extraction is added, and concentration obtains yellow crystalline substance after static a couple of days Body N- (4- isopropyls -2,6- bis- (benzhydryl) phenyl) -3,5- di-t-butyl -2- oxygen condensate Schiff base rare-earth ytterbium iodide；Wherein, N- (4- isopropyls -2,6- bis- (benzhydryl) phenyl) -3,5- di-t-butyl -2- oxygen schiff bases sylvite and triiodide ytterbium molar ratio It is 1: 1-1.5；Its reaction equation is as follows：
Application of the schiff bases ytterbium iodide as catalyst in the hydroboration of catalysis aldehydes or ketones.
The application, includes the following steps：Under the conditions of anhydrous and oxygen-free, by N- ((the hexichol first of 4- isopropyls -2,6- bis- Base) phenyl) -3,5- di-t-butyl -2- oxygen condensate Schiff base rare-earth ytterbium iodide are dissolved in solvent, and pinacol borine is added, adds Aldehydes or ketones react at room temperature 30min.
The molar ratio of the aldehyde and catalyst is 1000:1, the molar ratio of ketone and catalyst is 200:1.
Advantageous effect：Compared with prior art, the present invention has following advantages：
1) schiff bases ytterbium iodide of the present invention are new compound, develop new and effective schiff bases ytterbium metal Catalyst.
2) preparation method disclosed by the invention, reaction process is simple to operation, required article small toxicity, safety collar in experiment It protects, product is easily purified, yield is high, and can be stored at room temperature.
3) condensate Schiff base rare-earth ytterbium iodide of the present invention can effectively be catalyzed the hydroboration of aldehyde and ketone.
Specific implementation mode
With reference to embodiment, the invention will be further described.
Embodiment 1
N- (4- isopropyls -2,6- bis- (benzhydryl) phenyl) -3,5- di-t-butyl -2- oxygen condensate Schiff base rare-earth ytterbium iodide Preparation, process is as follows：
Under anhydrous and oxygen-free, in single port reaction tube, bis- uncles of N- (4- isopropyls -2,6- bis- (benzhydryl) phenyl) -3,5- Butyl-2-hydroxy benzaldimine 1.46mmol is dissolved in 40mL tetrahydrofuran solutions, -80 DEG C, and hydrofining 1.46mmol is dissolved in It is added dropwise in 5mL tetrahydrofurans, reacts at room temperature 2h, triiodide ytterbium 1.46mmol is dissolved in 20mL tetrahydrofurans, -80 DEG C, dropwise Above-mentioned solution is added, reacts 10h, solvent is drained, and is added to 40mL toluene and is extracted, is concentrated into 10mL, and yellow crystalline substance is obtained after a couple of days Body, filtering, quality 0.82g, yield 60%.M.p.282-284℃.Elemental analysis：C100H104IN2O2Yb:C,72.10；H, 6.29；N,1.68.Found C,72.58；H,6.63；N,1.32.It is infrared：IR(KBr,cm-1):3429,3061,3028,2960, 2867,1626 (C=N), 1602,1571,1535,1495,1445,1400,1365,1307,1253,1162,1117,1 076, 1022,803,758,699,604,523。
Embodiment 2
N- (4- isopropyls -2,6- bis- (benzhydryl) phenyl) -3,5- di-t-butyl -2- oxygen condensate Schiff base rare-earth ytterbium iodide Preparation, process is as follows：
Under anhydrous and oxygen-free, in single port reaction tube, bis- uncles of N- (4- isopropyls -2,6- bis- (benzhydryl) phenyl) -3,5- Butyl-2-hydroxy benzaldimine 1.75mmol is dissolved in 40mL tetrahydrofuran solutions, -60 DEG C, and hydrofining 2.10mmol is dissolved in It is added dropwise in 5mL tetrahydrofurans, reacts at room temperature 3h, triiodide ytterbium 1.75mmol is dissolved in 20mL tetrahydrofurans, -60 DEG C, dropwise Above-mentioned solution is added, reacts 15h, solvent is drained, and is added to 40mL toluene and is extracted, is concentrated into 10mL, and yellow crystalline substance is obtained after a couple of days Body, filtering, quality 0.98g, yield 59%.M.p.282-284℃.Elemental analysis：C100H104IN2O2Yb:C,72.10；H, 6.29；N,1.68.Found C,72.58；H,6.63；N, 1.32. are infrared：IR(KBr,cm-1):3429,3061,3028,2960, 2867,1626 (C=N), 1602,1571,1535,1495,1445,1400,1365,1307,1253,1162,1117,1 076, 1022,803,758,699,604,523。
Embodiment 3
N- (4- isopropyls -2,6- bis- (benzhydryl) phenyl) -3,5- di-t-butyl -2- oxygen condensate Schiff base rare-earth ytterbium iodide Preparation, process is as follows：
Under anhydrous and oxygen-free, in single port reaction tube, bis- uncles of N- (4- isopropyls -2,6- bis- (benzhydryl) phenyl) -3,5- Butyl-2-hydroxy benzaldimine 1.75mmol is dissolved in 40mL tetrahydrofuran solutions, -40 DEG C, and hydrofining 2.10mmol is dissolved in It is added dropwise in 5mL tetrahydrofurans, reacts at room temperature 4h, triiodide ytterbium 1.75mmol is dissolved in 20mL tetrahydrofurans, -40 DEG C, dropwise Above-mentioned solution is added, reacts 20h, solvent is drained, and is added to 40mL toluene and is extracted, is concentrated into 10mL, and yellow crystalline substance is obtained after a couple of days Body, filtering, quality 0.99g, yield 61%.M.p.282-284℃.Elemental analysis：C100H104IN2O2Yb:C,72.10；H, 6.29；N,1.68.Found C,72.58；H,6.63；N, 1.32. are infrared：IR(KBr,cm-1):3429,3061,3028,2960, 2867,1626 (C=N), 1602,1571,1535,1495,1445,1400,1365,1307,1253,1162,1117,1 076, 1022,803,758,699,604,523。
Embodiment 4
N- (4- isopropyls -2,6- bis- (benzhydryl) phenyl) -3,5- di-t-butyl -2- oxygen condensate Schiff base rare-earth ytterbium iodide Catalysis benzaldehyde is reacted with pinacol borine, and process is as follows：
In glove box, equipped with 0.5mL C6D6Nuclear magnetic tube in sequentially add condensate Schiff base rare-earth ytterbium iodide 0.001mmol, benzaldehyde 1mmol and pinacol borine 1.2mmol, are then moved out glove box, react 10min, pass through core Magnetic spectrum figure obtains the rate of output 99%.
Embodiment 5
N- (4- isopropyls -2,6- bis- (benzhydryl) phenyl) -3,5- di-t-butyl -2- oxygen condensate Schiff base rare-earth ytterbium iodide Catalysis o-chlorobenzaldehyde is reacted with pinacol borine, and process is as follows：
In glove box, equipped with 0.5mL C6D6Nuclear magnetic tube in sequentially add schiff bases ytterbium iodide 0.001mmol, Then o-chlorobenzaldehyde 1mmol and pinacol borine 1.2mmol is moved out glove box, react 10min, pass through nuclear magnetic spectrogram Obtain the rate of output 99%.
Embodiment 6
N- (4- isopropyls -2,6- bis- (benzhydryl) phenyl) -3,5- di-t-butyl -2- oxygen condensate Schiff base rare-earth ytterbium iodide Catalysis 4- chlorobenzaldehydes are reacted with pinacol borine, and process is as follows：
In glove box, equipped with 0.5mL C6D6Nuclear magnetic tube in sequentially add schiff bases ytterbium iodide 0.001mmol, Then 4- chlorobenzaldehydes 1mmol and pinacol borine 1.2mmol is moved out glove box, react 80min, pass through nuclear magnetic spectrogram Obtain the rate of output 98%.
Embodiment 7
N- (4- isopropyls -2,6- bis- (benzhydryl) phenyl) -3,5- di-t-butyl -2- oxygen condensate Schiff base rare-earth ytterbium iodide Catalysis o fluorobenzaldehyde is reacted with pinacol borine, and process is as follows：
In glove box, equipped with 0.5mL C6D6Nuclear magnetic tube in sequentially add schiff bases ytterbium iodide 0.001mmol, Then o fluorobenzaldehyde 1mmol and pinacol borine 1.2mmol is moved out glove box, react 10min, pass through nuclear magnetic spectrogram Obtain the rate of output 99%.
Embodiment 8
N- (4- isopropyls -2,6- bis- (benzhydryl) phenyl) -3,5- di-t-butyl -2- oxygen condensate Schiff base rare-earth ytterbium iodide Catalysis 4- fluorobenzaldehydes are reacted with pinacol borine, and process is as follows：
In glove box, equipped with 0.5mL C6D6Nuclear magnetic tube in sequentially add schiff bases ytterbium iodide 0.001mmol, Then 4- fluorobenzaldehydes 1mmol and pinacol borine 1.2mmol is moved out glove box, react 50min, pass through nuclear magnetic spectrogram Obtain the rate of output 98%.
Embodiment 9
N- (4- isopropyls -2,6- bis- (benzhydryl) phenyl) -3,5- di-t-butyl -2- oxygen condensate Schiff base rare-earth ytterbium iodide Catalysis 4- (dimethylamino) benzaldehydes are reacted with pinacol borine, and process is as follows：
In glove box, equipped with 0.5mL C6D6Nuclear magnetic tube in sequentially add schiff bases ytterbium iodide 0.001mmol, Then 4- (dimethylamino) benzaldehyde 1mmol and pinacol borine 1.2mmol is moved out glove box, react 10min, leads to It crosses nuclear magnetic spectrogram and obtains the rate of output 99%.
Embodiment 10
N- (4- isopropyls -2,6- bis- (benzhydryl) phenyl) -3,5- di-t-butyl -2- oxygen condensate Schiff base rare-earth ytterbium iodide Catalysis p-tolyl aldehyde is reacted with pinacol borine, and process is as follows：
In glove box, equipped with 0.5mL C6D6Nuclear magnetic tube in sequentially add schiff bases ytterbium iodide 0.001mmol, Then p-tolyl aldehyde 1mmol and pinacol borine 1.2mmol is moved out glove box, react 10min, composed by nuclear-magnetism Scheme to obtain the rate of output 99%.
Embodiment 11
N- (4- isopropyls -2,6- bis- (benzhydryl) phenyl) -3,5- di-t-butyl -2- oxygen condensate Schiff base rare-earth ytterbium iodide Catalysis 4- nitrobenzaldehydes are reacted with pinacol borine, and process is as follows：
In glove box, equipped with 0.5mL C6D6Nuclear magnetic tube in sequentially add schiff bases ytterbium iodide 0.001mmol, Then 4- nitrobenzaldehydes 1mmol and pinacol borine 1.2mmol is moved out glove box, react 10min, composed by nuclear-magnetism Scheme to obtain the rate of output 99%.
Embodiment 12
N- (4- isopropyls -2,6- bis- (benzhydryl) phenyl) -3,5- di-t-butyl -2- oxygen condensate Schiff base rare-earth ytterbium iodide Catalysis p-anisaldehyde is reacted with pinacol borine, and process is as follows：
In glove box, equipped with 0.5mL C6D6Nuclear magnetic tube in sequentially add schiff bases ytterbium iodide 0.001mmol, Then p-anisaldehyde 1mmol and pinacol borine 1.2mmol is moved out glove box, react 10min, obtained by nuclear magnetic spectrogram The rate of output 99%.
Embodiment 13
N- (4- isopropyls -2,6- bis- (benzhydryl) phenyl) -3,5- di-t-butyl -2- oxygen condensate Schiff base rare-earth ytterbium iodide Catalysis cyclohexyl formaldehyde is reacted with pinacol borine, and process is as follows：
In glove box, equipped with 0.5mL C6D6Nuclear magnetic tube in sequentially add schiff bases ytterbium iodide 0.001mmol, Then cyclohexyl formaldehyde 1mmol and pinacol borine 1.2mmol is moved out glove box, react 10min, composed by nuclear-magnetism Scheme to obtain the rate of output 99%.
Embodiment 14
N- (4- isopropyls -2,6- bis- (benzhydryl) phenyl) -3,5- di-t-butyl -2- oxygen condensate Schiff base rare-earth ytterbium iodide Spirit catalytic of cinnamaldehyde is reacted with pinacol borine, and process is as follows：
In glove box, equipped with 0.5mL C6D6Nuclear magnetic tube in sequentially add schiff bases ytterbium iodide 0.001mmol, Then cinnamic acid 1mmol and pinacol borine 1.2mmol is moved out glove box, react 10min, obtained by nuclear magnetic spectrogram Yield 99%.
Embodiment 15
N- (4- isopropyls -2,6- bis- (benzhydryl) phenyl) -3,5- di-t-butyl -2- oxygen condensate Schiff base rare-earth ytterbium iodide Catalysis 9- anthraldehydes are reacted with pinacol borine, and process is as follows：
In glove box, equipped with 0.5mL C6D6Nuclear magnetic tube in sequentially add schiff bases ytterbium iodide 0.001mmol, Then 9- anthraldehydes 1mmol and pinacol borine 1.2mmol is moved out glove box, react 10min, obtained by nuclear magnetic spectrogram The rate of output 99%.
Embodiment 16
N- (4- isopropyls -2,6- bis- (benzhydryl) phenyl) -3,5- di-t-butyl -2- oxygen condensate Schiff base rare-earth ytterbium iodide Catalysis 2 thiophene carboxaldehyde is reacted with pinacol borine, and process is as follows：
In glove box, equipped with 0.5mL C6D6Nuclear magnetic tube in sequentially add schiff bases ytterbium iodide 0.001mmol, Then 2 thiophene carboxaldehyde 1mmol and pinacol borine 1.2mmol is moved out glove box, react 60min, pass through nuclear magnetic spectrogram Obtain the rate of output 98%.
Embodiment 17
N- (4- isopropyls -2,6- bis- (benzhydryl) phenyl) -3,5- di-t-butyl -2- oxygen condensate Schiff base rare-earth ytterbium iodide Catalysis m-hydroxybenzaldehyde is reacted with pinacol borine, and process is as follows：
In glove box, equipped with 0.5mL C6D6Nuclear magnetic tube in sequentially add schiff bases ytterbium iodide 0.001mmol, Then m-hydroxybenzaldehyde 1mmol and pinacol borine 1.2mmol is moved out glove box, react 60min, composed by nuclear-magnetism Scheme to obtain the rate of output 98%.
Embodiment 18
N- (4- isopropyls -2,6- bis- (benzhydryl) phenyl) -3,5- di-t-butyl -2- oxygen condensate Schiff base rare-earth ytterbium iodide Catalysis acetophenone is reacted with pinacol borine, and process is as follows：
In glove box, equipped with 0.5mL C6D6Nuclear magnetic tube in sequentially add schiff bases ytterbium iodide 0.005mmol, Then acetophenone 1mmol and pinacol borine 1.2mmol is moved out glove box, react 50min, obtained by nuclear magnetic spectrogram Yield 98%.
Embodiment 19
N- (4- isopropyls -2,6- bis- (benzhydryl) phenyl) -3,5- di-t-butyl -2- oxygen condensate Schiff base rare-earth ytterbium iodide Catalysis o-fluoro acetophenone is reacted with pinacol borine, and process is as follows：
In glove box, equipped with 0.5mL C6D6Nuclear magnetic tube in sequentially add schiff bases ytterbium iodide 0.005mmol, Then o-fluoro acetophenone 1mmol and pinacol borine 1.2mmol is moved out glove box, react 15min, pass through nuclear magnetic spectrogram Obtain the rate of output 99%.
Embodiment 20
N- (4- isopropyls -2,6- bis- (benzhydryl) phenyl) -3,5- di-t-butyl -2- oxygen condensate Schiff base rare-earth ytterbium iodide Catalysis p-nitroacetophenone is reacted with pinacol borine, and process is as follows：
In glove box, equipped with 0.5mL C6D6Nuclear magnetic tube in sequentially add schiff bases ytterbium iodide 0.005mmol, Then p-nitroacetophenone 1mmol and pinacol borine 1.2mmol is moved out glove box, react 15min, composed by nuclear-magnetism Scheme to obtain the rate of output 99%.
Embodiment 21
N- (4- isopropyls -2,6- bis- (benzhydryl) phenyl) -3,5- di-t-butyl -2- oxygen condensate Schiff base rare-earth ytterbium iodide Catalysis 4-Acetylbenzonitrile is reacted with pinacol borine, and process is as follows：
In glove box, equipped with 0.5mL C6D6Nuclear magnetic tube in sequentially add schiff bases ytterbium iodide 0.005mmol, Then 4-Acetylbenzonitrile 1mmol and pinacol borine 1.2mmol is moved out glove box, react 3h, obtained by nuclear magnetic spectrogram The rate of output 92%.
Embodiment 22
N- (4- isopropyls -2,6- bis- (benzhydryl) phenyl) -3,5- di-t-butyl -2- oxygen condensate Schiff base rare-earth ytterbium iodide Catalysis benzophenone is reacted with pinacol borine, and process is as follows：
In glove box, equipped with 0.5mL C6D6Nuclear magnetic tube in sequentially add schiff bases ytterbium iodide 0.005mmol, Then benzophenone 1mmol and pinacol borine 1.2mmol is moved out glove box, react 1h, must be produced by nuclear magnetic spectrogram Rate 98%.
Embodiment 23
N- (4- isopropyls -2,6- bis- (benzhydryl) phenyl) -3,5- di-t-butyl -2- oxygen condensate Schiff base rare-earth ytterbium iodide Catalyzing iso-butane base phenyl ketone is reacted with pinacol borine, and process is as follows：
In glove box, equipped with 0.5mL C6D6Nuclear magnetic tube in sequentially add schiff bases ytterbium iodide 0.005mmol, Then isobutyl phenyl ketone 1mmol and pinacol borine 1.2mmol is moved out glove box, react 10min, composed by nuclear-magnetism Scheme to obtain the rate of output 99%.
Embodiment 24
N- (4- isopropyls -2,6- bis- (benzhydryl) phenyl) -3,5- di-t-butyl -2- oxygen condensate Schiff base rare-earth ytterbium iodide Catalysis acetanisole is reacted with pinacol borine, and process is as follows：
In glove box, equipped with 0.5mL C6D6Nuclear magnetic tube in sequentially add schiff bases ytterbium iodide 0.005mmol, Then acetanisole 1mmol and pinacol borine 1.2mmol is moved out glove box, react 50min, pass through nuclear-magnetism Spectrogram obtains the rate of output 98%.
Embodiment 25
N- (4- isopropyls -2,6- bis- (benzhydryl) phenyl) -3,5- di-t-butyl -2- oxygen condensate Schiff base rare-earth ytterbium iodide It is catalyzed 2', 4', 6'- trimethylacetophenones are reacted with pinacol borine, and process is as follows：
In glove box, equipped with 0.5mL C6D6Nuclear magnetic tube in sequentially add schiff bases ytterbium iodide 0.005mmol, Then 2', 4', 6'- trimethylacetophenone 1mmol and pinacol borine 1.2mmol are moved out glove box, react 48h, pass through Nuclear magnetic spectrogram obtains the rate of output 97%.
Embodiment 26
N- (4- isopropyls -2,6- bis- (benzhydryl) phenyl) -3,5- di-t-butyl -2- oxygen condensate Schiff base rare-earth ytterbium iodide Catalysis of pimelinketone is reacted with pinacol borine, and process is as follows：
In glove box, equipped with 0.5mL C6D6Nuclear magnetic tube in sequentially add schiff bases ytterbium iodide 0.005mmol, Then cyclohexanone 1mmol and pinacol borine 1.2mmol is moved out glove box, react 10min, obtained by nuclear magnetic spectrogram Yield 99%.
Embodiment 27
N- (4- isopropyls -2,6- bis- (benzhydryl) phenyl) -3,5- di-t-butyl -2- oxygen condensate Schiff base rare-earth ytterbium iodide Catalysis cyclohexyl ketone is reacted with pinacol borine, and process is as follows：
In glove box, equipped with 0.5mL C6D6Nuclear magnetic tube in sequentially add schiff bases ytterbium iodide 0.005mmol, Then cyclohexyl ketone 1mmol and pinacol borine 1.2mmol is moved out glove box, react 10min, pass through nuclear magnetic spectrogram Obtain the rate of output 99%.
Embodiment 28
N- (4- isopropyls -2,6- bis- (benzhydryl) phenyl) -3,5- di-t-butyl -2- oxygen condensate Schiff base rare-earth ytterbium iodide Catalysis 4'- aminoacetophenones are reacted with pinacol borine, and process is as follows：
In glove box, equipped with 0.5mL C6D6Nuclear magnetic tube in sequentially add schiff bases ytterbium iodide 0.005mmol, Then 4'- aminoacetophenones 1mmol and pinacol borine 1.2mmol is moved out glove box, react 4.5h, composed by nuclear-magnetism Scheme to obtain the rate of output 98%.

Claims (6)

1. a kind of condensate Schiff base rare-earth ytterbium iodide, are：Bis- tertiary fourths of N- (4- isopropyls -2,6- bis- (benzhydryl) phenyl) -3,5- Base -2- oxygen condensate Schiff base rare-earth ytterbium iodide, structural formula are as follows：
2. a kind of method preparing schiff bases ytterbium iodide described in claim 1, which is characterized in that include the following steps：
(1) under the conditions of anhydrous and oxygen-free, in single port reaction tube, by N- (4- isopropyls -2,6- bis- (benzhydryl) phenyl) -3,5- bis- Tertiary butyl-Benzaldehyde,2-hydroxy imines is dissolved in tetrahydrofuran solution, -80--40 DEG C, and the tetrahydrofuran solution of hydrofining is dropwise Above-mentioned solution is added, reacts at room temperature 2-4h；Obtain N- (4- isopropyls -2,6- bis- (benzhydryl) phenyl) -3,5- di-t-butyls - 2- oxygen schiff bases sylvite；Wherein, N- (4- isopropyls -2,6- bis- (benzhydryl) phenyl) -3,5- di-t-butyl -2- hydroxy benzenes first Aldimine, hydrofining molar ratio be 1:1-1.5；
(2) under the conditions of anhydrous and oxygen-free, in single port reaction tube, triiodide ytterbium is dissolved in tetrahydrofuran, -80--40 DEG C, is added dropwise (1) solution reacts 10-20h, and solvent is drained, and toluene extraction is added, and concentration obtains yellow crystals N- (4- after standing a couple of days Isopropyl -2,6- bis- (benzhydryl) phenyl) -3,5- di-t-butyl -2- oxygen condensate Schiff base rare-earth ytterbium iodide；Wherein, (4- is different by N- Propyl -2,6- bis- (benzhydryl) phenyl) -3,5- di-t-butyl -2- oxygen schiff bases sylvite and triiodide ytterbium molar ratio be 1:1- 1.5。
3. N- (4- isopropyls -2,6- bis- (benzhydryl) phenyl) -3,5- di-t-butyl -2- oxygen Schiffs described in claim 1 Application of the alkali rare earth ytterbium iodide as catalyst in the hydroboration of catalysis aldehydes or ketones.
4. application according to claim 3, which is characterized in that include the following steps：Under the conditions of anhydrous and oxygen-free, by N- (4- isopropyls -2,6- bis- (benzhydryl) phenyl) -3,5- di-t-butyl -2- oxygen condensate Schiff base rare-earth ytterbium iodide are dissolved in solvent In, pinacol borine is added, adds aldehydes or ketones, reacts at room temperature 30min.
5. application according to claim 4, it is characterised in that：The molar ratio of aldehyde and catalyst is 1000:1.
6. application according to claim 4, it is characterised in that：The molar ratio of ketone and catalyst is 200:1.
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