CN102225943A - Preparation method of N-heterocyclic carbine complex - Google Patents
Preparation method of N-heterocyclic carbine complex Download PDFInfo
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- CN102225943A CN102225943A CN2011101079604A CN201110107960A CN102225943A CN 102225943 A CN102225943 A CN 102225943A CN 2011101079604 A CN2011101079604 A CN 2011101079604A CN 201110107960 A CN201110107960 A CN 201110107960A CN 102225943 A CN102225943 A CN 102225943A
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Abstract
The invention provides a preparation method of an N-heterocyclic carbine complex. The method comprises: reacting imidazolium with chloroauric acid or chloroaurate for 2 -48 hours in a molar ratio of (1:1) to (1:5) in the presences of a base and a solvent at the temperature of 50 DEG C-150 DEG C so as to obtain the N-heterocyclic carbine complex, wherein the base is 1-10 times that the molar weight of imidazolium, and the volume molar ratio of solvent to imidazolium is 0.5-20ml/mmol. The obtained N-heterocyclic carbine complex is further purified so as to obtain a pure product. Through controlling reaction temperature and reaction time, a monovalent N-heterocyclic carbine complex or a mixture of monovalent N-heterocyclic carbine and a trivalent monovalent N-heterocyclic carbine complex can be selectively obtained. The preparation method in the invention is simple to operate and purify, is insensitive to air and water in the reaction process, and has the advantages of short synthesis steps, cheap and available raw materials and the like.
Description
Technical field
The present invention relates to the preparation technology of azepine Cabbeen gold complex, specifically, relate to the preparation method of azepine Cabbeen gold complex.
Background technology
Azepine Cabbeen gold complex has good catalytic efficiency for the catalyzed reaction of alkynes and the decomposition reaction of diazonium compound.The preparation method of azepine Cabbeen gold complex is synthetic through three steps by imidazole salts at present:
Method one (Chem.Soc.Dalton Trans. (2004) 1034):
Method two (Organometallics 2010,29,4448-4458, and Organometallics 2005,24, and 24112418):
In the above method, (Me
2S) AuCl is synthesized by raw material hydrochloro-auric acid or chlor(o)aurate, synthetic method see document (Transition Metal Chemistry (and Dordrecht, Netherlands), 27 (2), 177-183; 200):
2010), then need the gold complex oxidation of azepine Cabbeen monovalence is got, and the condition strictness:
Azepine Cabbeen monovalence gold complex in the aforesaid method and azepine Cabbeen trivalent gold complex all need 3 above reactions of step just can make, have that route is long, cost is high, complicated operation, to shortcomings such as air and water sensitive, yield are low.
Summary of the invention
For overcoming the deficiencies in the prior art and defective, the invention provides a kind of preparation method of advantages of simplicity and high efficiency azepine Cabbeen gold complex.
The reaction formula of azepine Cabbeen gold complex preparation of the present invention is as follows:
In the formula: R
1, R
4Be C
1～C
12Alkyl, aryl, heteroaryl in a kind of; R
2, R
3Be hydrogen atom, C
1～C
12Alkyl, C
1～C
12Alkoxyl group, aryl, heteroaryl in a kind of; Described n=1 or 3; Described X be halogen ,-OTf ,-BF
4,-PF
6In any; Described Y be halogen ,-BF
4In a kind of; Described m=02, M are any among H, Na, the K;
Concrete steps are: imidazole salts A and hydrochloro-auric acid or chlor(o)aurate B be with 1: 1～1: 5 mol ratio, under the effect of alkali and solvent, in 25 ℃～150 ℃ reaction 2h～48h down, obtains azepine Cabbeen gold complex C; The molar weight of described alkali is 1～10 times of imidazole salts A molar weight, and the volume mol ratio of described solvent and imidazole salts A is 0.5～20ml/mmol.
Described azepine Cabbeen gold complex is the mixture of azepine Cabbeen monovalence gold complex or azepine Cabbeen monovalence gold complex and azepine Cabbeen trivalent gold complex.
The azepine Cabbeen gold complex C of preparation after short filtered through silica gel, is spin-dried for the methylene dichloride in the filtrate after dissolving with methylene dichloride, and surplus solution is again at C
5～C
6Disperse in alkane or the ether, obtain pure product azepine Cabbeen gold complex C; The volume mol ratio of methylene dichloride and imidazole salts A is 1～20ml/mmol.
Described alkali is any in yellow soda ash, salt of wormwood, cesium carbonate, sodium bicarbonate, saleratus, potassiumphosphate, sodium hydroxide, the potassium hydroxide.
Described solvent is pyridine, 3-chloropyridine, ethylene dichloride, water, 1, any in 4-dioxane, acetonitrile, toluene, chlorobenzene, the dimethylbenzene.
Change above-mentioned preparation method's temperature of reaction and reaction times,, obtain the mixture of azepine Cabbeen monovalence gold complex and azepine Cabbeen trivalent gold complex at 25 ℃～80 ℃ down during reaction 2h～10h; React 10h～48h down at 80 ℃～150 ℃, obtain azepine Cabbeen monovalence gold complex.
Compared with prior art, the present invention has the following advantages:
(1) preparation process of the present invention is simple, only can synthesize azepine Cabbeen gold complex efficiently by a simple step;
(2) the present invention is simple to operate, and reaction process is insensitive to empty G﹠W, and synthesis step is short, and the raw material that is adopted is cheap and easy to get, and the azepine Cabbeen gold complex purifying of preparation is simple.
Embodiment
Below in conjunction with embodiment the present invention is further detailed, but protection scope of the present invention is not limited to this.
Embodiment 1:[AuCl (IMes)] and [AuCl
3(IMes)] preparation
In flask, add magneton, and adding imidazole salts IMesHCl (47.7mg, 0.14mmol), KAuCl
42H
2O (58.1mg, 0.14mmol), Na
2CO
3(72.1mg, 0.68mmol), 3-chloropyridine (0.5ml), mixed solution reacts 2h down at 80 ℃.After the question response system is cooled to room temperature, add 1mlCH
2Cl
2Dissolving is filtered fast with short silica gel, gets filtrate, revolves the CH in the filtrate
2Cl
2After, surplus solution disperses to obtain white powdery solid 73.5mg in Skellysolve A, reaction yield: [AuCl (IMes)] is 28%; [AuCl
3(IMes)] be 60%.
Embodiment 2: in flask, add magneton, adding imidazole salts IMesHCl (47.7mg, 0.14mmol), KAuCl
42H
2O (290.5mg, 0.60mmol), Na
2CO
3(95.4mg, 0.90mmol), 3-chloropyridine (1.0ml), mixed solution reacts 10h down at 25 ℃.After the question response system is cooled to room temperature, add 1.5mlCH
2Cl
2Dissolving is filtered fast with short silica gel, gets filtrate, revolves the CH in the filtrate
2Cl
2After, surplus solution disperses to obtain white powdery solid 75.5mg in Skellysolve A, reaction yield: [AuCl (IMes)] is 30%; [AuCl
3(IMes)] be 63%.
The nuclear magnetic data of [AuCl (IMes)]: 1HNMR (CDCl3,400MHz): δ 2.10 (s, 12H), 2.35 (s, 6H), 6.99 (s, 4H), 7.10 (s, 2H); 13CNMR (CDCl3,100MHz): δ 17.8,21.1, and 122.2,129.5,134.6,134.7,139.8,173.4.
The nuclear magnetic data of [AuCl3 (IMes)]: 1HNMR (CDCl3,400MHz): δ 2.26 (s, 12H), 2.37 (s, 6H), 7.03 (s, 4H), 7.30 (s, 2H); 13CNMR (CDCl3,100MHz): δ 18.5,21.1, and 125.6,129.9,132.3,135.3,141.0,144.6.
Embodiment 3: in flask, add magneton, adding imidazole salts IMesHCl (47.7mg, 0.14mmol), KAuCl
4 2H
2O (58.1mg, 0.14mmol), K
2CO
3(14.8mg, 0.14mmol), 3-chloropyridine (2.5ml), mixed solution reacts 16h down at 80 ℃.After the question response system is cooled to room temperature, add 2.5mlCH
2Cl
2Dissolving is filtered fast with short silica gel, gets filtrate, revolves the CH in the filtrate
2Cl
2After, surplus solution disperses to obtain white powdery solid 48.7mg in Skellysolve A, reaction yield: [AuCl (IMes)] is 65%.
Embodiment 4: in flask, add magneton, adding imidazole salts IMesHCl (47.7mg, 0.14mmol), KAuCl
42H
2O (290.5mg, 0.60mmol), K
2CO
3(124.2mg, 0.90mmol), 3-chloropyridine (1.5ml), mixed solution reacts 24h down at 90 ℃.After the question response system is cooled to room temperature, add 1.0mlCH
2Cl
2Dissolving is filtered fast with short silica gel, gets filtrate, revolves the CH in the filtrate
2Cl
2After, surplus solution disperses to obtain white powdery solid 49.3mg in Skellysolve A, reaction yield: [AuCl (IMes)] is 69%.
Embodiment 5: in flask, add magneton, adding imidazole salts IMesHCl (47.7mg, 0.14mmol), NaAuCl
42H
2O (55.7mg, 0.14mmol), Na
2CO
3(159.0mg, 1.50mmol), 3-chloropyridine (0.5ml), mixed solution reacts 16h down at 100 ℃.After the question response system is cooled to room temperature, add 1.5mlCH
2Cl
2Dissolving is filtered fast with short silica gel, gets filtrate, revolves the CH in the filtrate
2Cl
2After, surplus solution disperses to obtain white powdery solid 59.5mg in Skellysolve A, reaction yield: [AuCl (IMes)] is 79%.
Embodiment 6: in flask, add magneton, adding imidazole salts IMesHCl (47.7mg, 0.14mmol), NaAuCl
42H
2O (278.5mg, 0.60mmol), Na
2CO
3(95.4mg, 0.90mmol), 3-chloropyridine (2.0ml), mixed solution reacts 48h down at 150 ℃.After the question response system is cooled to room temperature, add 1.5mlCH
2Cl
2Dissolving is filtered fast with short silica gel, gets filtrate, revolves the CH in the filtrate
2Cl
2After, surplus solution disperses to obtain white powdery solid 66.4mg in Skellysolve A, reaction yield: [AuCl (IMes)] is 85%.
Embodiment 7: in flask, add magneton, adding imidazole salts IMesHCl (47.7mg, 0.14mmol), NaAuCl
42H
2O (55.7mg, 0.14mmol), K
2CO
3(19.3mg, 0.14mmol), 3-chloropyridine (1.5ml), mixed solution reacts 10h down at 90 ℃.After the question response system is cooled to room temperature, add 2.5mlCH
2Cl
2Dissolving is filtered fast with short silica gel, gets filtrate, revolves the CH in the filtrate
2Cl
2After, surplus solution disperses to obtain white powdery solid 71.7mg in Skellysolve A, reaction yield: [AuCl (IMes)] is 58%, [AuCl
3(IMes)] be 32%.
Embodiment 8: in flask, add magneton, adding imidazole salts IMesHCl (47.7mg, 0.14mmol), NaAuCl
42H
2O (278.5mg, 0.60mmol), K
2CO
3(124.2mg, 0.90mmol), 3-chloropyridine (1.5ml), mixed solution reacts 40h down at 120 ℃.After the question response system is cooled to room temperature, add 2.0mlCH
2Cl
2Dissolving is filtered fast with short silica gel, gets filtrate, revolves the CH in the filtrate
2Cl
2After, surplus solution disperses to obtain white powdery solid 71.8mg in Skellysolve A, reaction yield: [AuCl (IMes)] is 58%, [AuCl
3(IMes)] be 32%.
Embodiment 9:[AuCl (SIMes)] preparation
In flask, add magneton, and adding imidazole salts SIMesHCl (48.0mg, 0.14mmol), NaAuCl
42H
2O (55.7mg, 0.14mmol), Na
2CO
3(159.0mg, 1.50mmol), 3-chloropyridine (2.5ml), mixed solution reacts 35h down at 90 ℃.After the question response system is cooled to room temperature, add 1.0mlCH
2Cl
2Dissolving is filtered fast with short silica gel, gets filtrate, revolves the CH in the filtrate
2Cl
2After, surplus solution disperses to obtain white powdery solid 46.6mg in Skellysolve A, reaction yield: pure [AuCl (SIMes)] is 72%.
Embodiment 10: in flask, add magneton, adding imidazole salts SIMesHCl (48.0mg, 0.14mmol), NaAuCl
42H
2O (278.5mg, 0.60mmol), Na
2CO
3(95.4mg, 0.90mmol), 3-chloropyridine (1.5ml), mixed solution reacts 25h down at 110 ℃.After the question response system is cooled to room temperature, add 1.5mlCH
2Cl
2Dissolving is filtered fast with short silica gel, gets filtrate, revolves the CH in the filtrate
2Cl
2After, surplus solution disperses to obtain white powdery solid 56.6mg in Skellysolve A, reaction yield: pure [AuCl (SIMes)] is 82%.
The nuclear magnetic data of [AuCl (SIMes)]:
1HNMR (CDCl
3, 400MHz): δ 2.30 (s, 6H), 2.32 (s, 12H), 3.99 (s, 4H), 6.94 (s, 4H);
13CNMR (CDCl
3, 100MHz): δ 18.0,21.1, and 50.7,129.8,134.6,135.5,139.0,195.1.
Embodiment 11: in flask, add magneton, adding imidazole salts SIMesHCl (48.0mg, 0.14mmol), KAuCl
42H
2O (58.1mg, 0.14mmol), Na
2CO
3(61.7mg, 0.45mmol), 3-chloropyridine (0.5ml), mixed solution reacts 30h down at 110 ℃.After the question response system is cooled to room temperature, add 2.0mlCH
2Cl
2Dissolving is filtered fast with short silica gel, gets filtrate, revolves the CH in the filtrate
2Cl
2After, surplus solution disperses to obtain white powdery solid 69.0mg in Skellysolve A, reaction yield: pure [AuCl (SIMes)] is 91%.
Embodiment 12: in flask, add magneton, adding imidazole salts SIMesHCl (48.0mg, 0.14mmol), KAuCl
42H
2O (290.5mg, 0.60mmol), Na
2CO
3(95.4mg, 0.90mmol), 3-chloropyridine (1.0ml), mixed solution reacts 15h down at 80 ℃.After the question response system is cooled to room temperature, add 2.0mlCH
2Cl
2Dissolving is filtered fast with short silica gel, gets filtrate, revolves the CH in the filtrate
2Cl
2After, surplus solution disperses to obtain white powdery solid 69.4mg in Skellysolve A, reaction yield: pure [AuCl (SIMes)] is 92%.
Embodiment 13:[AuCl (IPr)] preparation
In flask, add magneton, and adding imidazole salts IPrHCl (59.5mg, 0.14mmol), NaAuCl
42H
2O (55.7mg, 0.14mmol), Na
2CO
3(72.1mg, 0.68mmol), 3-chloropyridine (1.0ml), mixed solution reacts 35h down at 105 ℃.After the question response system is cooled to room temperature, add 2.5mlCH
2Cl
2Dissolving is filtered fast with short silica gel, gets filtrate, revolves the CH in the filtrate
2Cl
2After, surplus solution disperses to obtain white powdery solid 65.2mg in Skellysolve A, reaction yield: pure [AuCl (IPr)] is 75%.
Embodiment 14: in flask, add magneton, adding imidazole salts IPrHCl (59.5mg, 0.14mmol), NaAuCl
42H
2O (278.5mg, 0.60mmol), Na
2CO
3(72.1mg, 0.68mmol), 3-chloropyridine (1.0ml), mixed solution reacts 18h down at 125 ℃.After the question response system is cooled to room temperature, add 1.0mlCH
2Cl
2Dissolving is filtered fast with short silica gel, gets filtrate, revolves the CH in the filtrate
2Cl
2After, surplus solution disperses to obtain white powdery solid 67.7mg in Skellysolve A, reaction yield: pure [AuCl (IPr)] is 78%.
The nuclear magnetic data of [AuCl (IPr)]:
1HNMR (CDCl
3, 400MHz): δ 1.21 (d, 12H, J=6.8), 1.34 (d, 12H, J=6.8), 2.50-2.61 (m, 4H), 7.17 (s, 2H), 7.28 (d, 4H, J=8), 7.50 (t, 2H, J=8);
13CNMR (CDCl
3, 100MHz): δ 24.0,24.5, and 28.8,123.1,124.3,130.7,134.0,145.6,175.3.
Embodiment 15: in flask, add magneton, adding imidazole salts IPrHCl (59.5mg, 0.14mmol), KAuCl
42H
2O (58.1mg, 0.14mmol), Na
2CO
3(72.1mg, 0.68mmol), 3-chloropyridine (0.5ml), mixed solution reacts 45h down at 135 ℃.After the question response system is cooled to room temperature, add 1.5mlCH
2Cl
2Dissolving is filtered fast with short silica gel, gets filtrate, revolves the CH in the filtrate
2Cl
2After, surplus solution disperses to obtain white powdery solid 77.0mg in Skellysolve A, reaction yield: pure [AuCl (IPr)] is 89%.
Embodiment 16: in flask, add magneton, adding imidazole salts IPrHCl (59.5mg, 0.14mmol), KAuCl
42H
2O (290.5mg, 0.60mmol), Na
2CO
3(95.4mg, 0.90mmol), 3-chloropyridine (1.5ml), mixed solution reacts 24h down at 100 ℃.After the question response system is cooled to room temperature, add 1.0mlCH
2Cl
2Dissolving is filtered fast with short silica gel, gets filtrate, revolves the CH in the filtrate
2Cl
2After, surplus solution disperses to obtain white powdery solid 78.9mg in Skellysolve A, reaction yield: pure [AuCl (IPr)] is 90%.
Embodiment 17:[AuCl (SIPr)] preparation
In flask, add magneton, and adding imidazole salts SIPrHCl (59.8mg, 0.14mmol), NaAuCl
42H
2O (55.7mg, 0.14mmol), Na
2CO
3(159.0mg, 1.50mmol), 3-chloropyridine (2.5ml), mixed solution reacts 16h down at 80 ℃.After the question response system is cooled to room temperature, add 1.0mlCH
2Cl
2Dissolving is filtered fast with short silica gel, revolves CH
2Cl
2, surplus solution disperses to obtain white powdery solid 65.2mg in Skellysolve A, reaction yield: pure [AuCl (SIPr)] is 55%.
Embodiment 18: in flask, add magneton, adding imidazole salts SIPrHCl (59.8mg, 0.14mmol), NaAuCl
42H
2O (278.5mg, 0.60mmol), Na
2CO
3(95.4mg, 0.90mmol), 3-chloropyridine (1.0ml), mixed solution reacts 12h down at 100 ℃.After the question response system is cooled to room temperature, add 2.0mlCH
2Cl
2Dissolving is filtered fast with short silica gel, gets filtrate, revolves the CH in the filtrate
2Cl
2After, surplus solution disperses to obtain white powdery solid 76.1mg in Skellysolve A, reaction yield: pure [AuCl (SIPr)] is 76%.
The nuclear magnetic data of [AuCl (SIPr)]:
1HNMR (CDCl
3, 400MHz): δ 1.33 (d, 12H, J=6.8), 1.41 (d, 12H, J=6.8), 3.00-3.10 (m, 4H), 4.04 (s, 4H), 7.22 (d, 4H, J=7.6), 7.41 (t, 2H, J=7.6);
13CNMR (CDCl
3, 100MHz): δ 24.1,25.1, and 29.0,53.5,124.6,130.0,134.0,146.5,196.0.
Embodiment 19: in flask, add magneton, adding imidazole salts SIPrHCl (59.8mg, 0.14mmol), KAuCl
42H
2O (58.1mg, 0.14mmol), Na
2CO
3(82.3mg, 0.60mmol), 3-chloropyridine (0.5ml), mixed solution reacts 16h down at 100 ℃.After the question response system is cooled to room temperature, add 1.5mlCH
2Cl
2Dissolving is filtered fast with short silica gel, revolves CH
2Cl
2, surplus solution disperses to obtain white powdery solid 77.0mg in Skellysolve A, reaction yield: pure [AuCl (SIPr)] is 74%.
Embodiment 20: in flask, add magneton, adding imidazole salts SIPrHCl (59.8mg, 0.14mmol), KAuCl
42H
2O (278.5mg, 0.60mmol), Na
2CO
3(95.4mg, 0.90mmol), 3-chloropyridine (1.0ml), mixed solution reacts 12h down at 80 ℃.After the question response system is cooled to room temperature, add 2.0mlCH
2Cl
2Dissolving is filtered fast with short silica gel, revolves CH
2Cl
2, surplus solution disperses to obtain white powdery solid 77.5mg in Skellysolve A, reaction yield: pure [AuCl (SIPr)] is 75%.
Claims (7)
1. the preparation method of azepine Cabbeen gold complex, it is characterized in that: the preparation feedback formula of described azepine Cabbeen gold complex is:
In the formula: R
1, R
4Be C
1~ C
12A kind of in alkyl, aryl, the heteroaryl; R
2, R
3Be hydrogen atom, C
1~ C
12Alkyl, C
1~ C
12A kind of in alkoxyl group, aryl, the heteroaryl; Described n=1 or 3; Described X be halogen ,-OTf ,-BF
4,-PF
6In any; Described Y be halogen ,-BF
4In any; Described m=0 ~ 2, M is any among H, Na, the K;
Concrete steps are: imidazole salts A and hydrochloro-auric acid or chlor(o)aurate B are with the mol ratio of 1:1 ~ 1:5, and under the effect of alkali and solvent, reaction 2h ~ 48h obtains azepine Cabbeen gold complex C under 25 ℃ ~ 150 ℃; Described alkali molar weight is 1 ~ 10 times of imidazole salts A molar weight, and the volume mol ratio of described solvent and imidazole salts A is 0.5 ~ 20ml/mmol.
2. preparation method according to claim 1 is characterized in that: described alkali is any in yellow soda ash, salt of wormwood, cesium carbonate, sodium bicarbonate, saleratus, potassiumphosphate, sodium hydroxide, the potassium hydroxide.
3. synthetic method according to claim 1 is characterized in that: described solvent is pyridine, 3-chloropyridine, ethylene dichloride, water, 1, any in 4-dioxane, acetonitrile, toluene, chlorobenzene, the dimethylbenzene.
4. preparation method according to claim 1 is characterized in that: described azepine Cabbeen gold complex is the mixture of azepine Cabbeen monovalence gold complex or azepine Cabbeen monovalence gold complex and azepine Cabbeen trivalent gold complex.
5. according to each described preparation method of claim 1 ~ 3, it is characterized in that: under 25 ℃ ~ 80 ℃, react 2h ~ 10h, obtain the mixture of azepine Cabbeen monovalence gold complex and azepine Cabbeen trivalent gold complex.
6. according to each described preparation method of claim 1 ~ 3, it is characterized in that: reaction 10h ~ 48h under 80 ℃ ~ 150 ℃ obtains azepine Cabbeen monovalence gold complex.
7. preparation method according to claim 1 is characterized in that: described azepine Cabbeen gold complex C dissolves through methylene dichloride, again after short filtered through silica gel, remove the methylene dichloride in the filtrate after, surplus solution is again through C
5~ C
6Alkane or ether disperse, obtain pure product azepine Cabbeen gold complex C; The volume mol ratio of described methylene dichloride and imidazole salts A is 1 ~ 20ml/mmol.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107501372A (en) * | 2017-09-07 | 2017-12-22 | 赣南师范大学 | Chiral N-heterocyclic carbine gold compound and its production and use |
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|---|---|---|---|---|
| CN101402644A (en) * | 2008-10-31 | 2009-04-08 | 浙江大学 | Production method for metal aza ring carbene complex |
| CN101454329A (en) * | 2006-05-25 | 2009-06-10 | 宇部兴产株式会社 | Substituted phenylethynyl gold-nitrogenated heterocyclic carbene complex |
| WO2009152219A1 (en) * | 2008-06-11 | 2009-12-17 | Henkel Corporation | (n-heterocyclic carbene) copper salt complex as latent click catalyst |
| US7767841B1 (en) * | 2007-04-05 | 2010-08-03 | University Of New Orleans Research And Technology Foundation, Inc. | Gold complexes for catalysIS and preparation thereof |
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2011
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101454329A (en) * | 2006-05-25 | 2009-06-10 | 宇部兴产株式会社 | Substituted phenylethynyl gold-nitrogenated heterocyclic carbene complex |
| US7767841B1 (en) * | 2007-04-05 | 2010-08-03 | University Of New Orleans Research And Technology Foundation, Inc. | Gold complexes for catalysIS and preparation thereof |
| WO2009152219A1 (en) * | 2008-06-11 | 2009-12-17 | Henkel Corporation | (n-heterocyclic carbene) copper salt complex as latent click catalyst |
| CN101402644A (en) * | 2008-10-31 | 2009-04-08 | 浙江大学 | Production method for metal aza ring carbene complex |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN107501372A (en) * | 2017-09-07 | 2017-12-22 | 赣南师范大学 | Chiral N-heterocyclic carbine gold compound and its production and use |
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