Name: 244187-81-3|1,3-Bis(2,6-diisopropylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene|98%
Brand: Ambeed
SKU: A299206
Rating: 91 (32 reviews)

1
[ 244187-81-3 ]
[ 258278-31-8 ]

Reference： [1]Tetrahedron,1999,vol. 55,p. 14523 - 14534
[2]Organometallics,2010,vol. 29,p. 394 - 402

2
[ 250285-32-6 ]
[ 244187-81-3 ]

Reference： [1]Journal of the American Chemical Society,2006,vol. 128,p. 5602 - 5603
[2]Angewandte Chemie - International Edition,2012,vol. 51,p. 11354 - 11357,4
Angewandte Chemie,2012,vol. 124,p. 11516 - 11519
[3]Chemical Communications,2019,vol. 55,p. 9355 - 9358
[4]Organometallics,2015,vol. 34,p. 3480 - 3496
[5]Tetrahedron,1999,vol. 55,p. 14523 - 14534
[6]Advanced Synthesis and Catalysis,2014,vol. 356,p. 2281 - 2292
[7]Advanced Synthesis and Catalysis,2016,vol. 358,p. 622 - 630
[8]Journal of Organometallic Chemistry,2000,vol. 606,p. 49 - 54
[9]ChemCatChem,2018,vol. 10,p. 2450 - 2457
[10]Organic and Biomolecular Chemistry,2010,vol. 8,p. 1695 - 1705
[11]Chemistry - A European Journal,2011,vol. 17,p. 9911 - 9914
[12]Organometallics,2012,vol. 31,p. 6312 - 6316
[13]Organic Process Research and Development,2014,vol. 18,p. 1041 - 1044
[14]Organic Letters,2015,vol. 17,p. 544 - 547
[15]Organic Process Research and Development,2016,vol. 20,p. 911 - 920
[16]Organometallics,2018,vol. 37,p. 4753 - 4762
[17]Journal of the American Chemical Society,2019,vol. 141,p. 17112 - 17116
[18]European Journal of Organic Chemistry,2019,vol. 2019,p. 6968 - 6972
[19]Organometallics,2022,vol. 41,p. 486 - 496

3
[ 244187-81-3 ]
C₂₇H₃₆N₂*BBr₃ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2007,vol. 129,p. 12412 - 12413

4
[ 24544-04-5 ]
[ 244187-81-3 ]

Reference： [1]Journal of Organometallic Chemistry,2000,vol. 606,p. 49 - 54
[2]Tetrahedron,1999,vol. 55,p. 14523 - 14534
[3]Organic Process Research and Development,2014,vol. 18,p. 1041 - 1044
[4]Organic Letters,2015,vol. 17,p. 544 - 547
[5]Advanced Synthesis and Catalysis,2016,vol. 358,p. 622 - 630
[6]Patent: JP5662491,2015,B2
[7]ChemCatChem,2018,vol. 10,p. 2450 - 2457
[8]Chemical Communications,2019,vol. 55,p. 9355 - 9358

5
[ 74663-75-5 ]
[ 244187-81-3 ]

Reference： [1]Tetrahedron,1999,vol. 55,p. 14523 - 14534
[2]Organic Process Research and Development,2014,vol. 18,p. 1041 - 1044
[3]Organic Letters,2015,vol. 17,p. 544 - 547
[4]ChemCatChem,2018,vol. 10,p. 2450 - 2457
[5]Chemical Communications,2019,vol. 55,p. 9355 - 9358

6
bis(acetylacetonato)palladium(II) [ No CAS ]
[ 244187-81-3 ]
(IPr)Pd(acac)2 [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	In toluene; at 20℃; for 2h;Product distribution / selectivity;	In a glove box, a Schlenk flask equipped with a magnetic bar was loaded with free carbene <strong>[244187-81-3]IPr</strong> (855 mg, 2.2 mmol), Pd(acac)2 (609 mg, 2 mmol) and dry toluene (30 mL), and sealed with a rubber cap. The mixture was stirred at room temperature for two hours. The solvent was evaporated in vacuo and THF (25 mL) was added. The solution was filtered and the solid washed with THF (2x5 mL). The solvent was evaporated in vacuo; the complex was then triturated with cold pentane (25 mL) and filtered out the solution. Recrystallization in a chloroform/pentane mixture (25/75) yielded 1.28 g (93%) of the desired compound. 1H-NMR (400 MHz, C6D6): 8D 7.28-7.24 (m, 2H), 7.18 (d, J= 8.0 Hz, 4H), 6.47 (s, 2H), 5.90 (s, IH), 4.78 (s, IH), 2.88 (q, J= 6.8 Hz, 4H), 2.63 (d, J= 0.8 Hz, 3H), 2.01 (d, J= 0.8 Hz, 3H), EPO <DP n="31"/>1.63 (s, 3H), 1.35 (d, J= 6.8, 12H)3 1.31 (s, 3H), 0.97 (d, J= 6.8, 12H). 13C-NMR (100 MHz, C6D6): 207.5, 192.9, 188.1, 185.6, 183.3, 161.2, 146.9, 135.9, 131.2, 130.4, 125.7, 125.2, 124.7, 124.5, 104.8, 100.3, 47.2, 31.9, 31.5, 29.3, 29.0, 28.9, 28.1, 27.0, 26.5, 26.2, 25.1, 24.0, 23.8, 23.4. Elemental Analysis: Anal. Calcd.: C, 64.11; H, 7.27; N, 4.04. Found: C, 63.89; H, 7.06; N: 3.86.; In comparison with the reported (PPh3)Pd(acac)2, a NHC-bearing analogue has been synthesized by the procedure of Scheme 1, shown below. Direct reaction of free carbene <strong>[244187-81-3]IPr</strong> with Pd(acac)2 at room temperature in dry toluene yielded (<strong>[244187-81-3]IPr</strong>)Pd(acac)2 (Pd Complex 1) in very high yield as a yellow powder. The presence of one oxygen-chelating ligand and one C-bound ligand in the complex was apparent by both 13C and 1H NMR. In the 13C NMR spectrum, 6 different signals above 160 ppm: 207.5 (C-bound acac), 192.9, 188.1, 185.6, 183.3 (carbonyl carbons) and 161.2 (carbenic carbon) were observed. In the 1H NMR spectrum, four methyl- proton singlet signals were observed each at 2.63, 2.01, 1.63 and 1.31, together with two signals at 5.90 and 4.78. The lowest-field methyl peaks are assigned to the carbon-bonded acac, together with the lowest-field methenic hydrogen, while the other three signals are assigned to the oxygen-chelating ligand. It is of note that the PPh3 analogue showed only one peak for the methyls of the carbon bound ligand, due to free rotation. Clearly, the sterically demanding NHC ligand inhibits this rotation. The disposition of the ligands was unequivocally assigned when the crystal structure was resolved by X-ray diffraction. A square planar configuration around EPO <DP n="13"/>the palladium center can be observed, with nearly no distortion. As expected, the Pd-C carbenic distance is in the range of a single Pd-C bond. The Pd-O bond opposite to the NHC is elongated compared to the other Pd-O bond due to a strong trans effect.Scheme 1. Synthetic path leading to (<strong>[244187-81-3]IPr</strong>)Pd(acac)2 (Pd Complex 1)1.1 equivalentsR = 2,6-diisopropylphenylPd Complex 1

Reference： [1]Patent: WO2006/128097,2006,A1 .Location in patent: Page/Page column 28-29, 10-11

7
[ 16853-85-3 ]
[ 244187-81-3 ]
[ 478971-10-7 ]

Yield	Reaction Conditions	Operation in experiment
760 mg	In diethyl ether; at -45 - 20℃; for 24h;	Complex AlH3·<strong>[244187-81-3]IDipp</strong>, [(CH3)2CH]2C6H3}2·N2C3H2AlH3, was prepared according to the procedure[23]. 1,3-Bis (2,6-diisopropylphenyl)-1,3-dihydro-2Himidazol-2-ylidene (<strong>[244187-81-3]IDipp</strong>) (0.8 g, 2.06 mmol) wasdissolved in 15 mL of diethyl ether and added to a solutionof LiAlH4 (0.08 g, 2.06 mmol) in 5 mL of diethyl etherat 45. The resulting mixture was stirred for 1 daywith spontaneous heating to room temperature. Afterremoving the ether, the reaction product was extractedthree times with toluene, and then LiH was filtering out.After removal of toluene, 760 mg of the reaction productwas obtained. 1 NMR spectrum (deuterobenzene-d6) δ,ppm: 1.07 d (12H, CH3,3J 6.9 Hz), 1.42 d (12H, CH3,3J 6.9 Hz), 2.71 br. s (4H, CH), 3.67 br. s (3H, AlH3),6.47 br. s (2H, N2C3H2), 7.12 d (4H, Hm, 3JHH 7.7 Hz),7.25 t (2H, , 3JHH 7.6 Hz).The results of NMR studiesare consistent with the published data [23].

Reference： [1]Journal of Organometallic Chemistry,2002,vol. 656,p. 203 - 210
[2]Chemistry - A European Journal,2017,vol. 23,p. 12387 - 12398
[3]Russian Journal of General Chemistry,2021,vol. 91,p. 1969 - 1976
Zh. Obshch. Khim.,2021,vol. 91,p. 1524 - 1532

8
[ 60-29-7 ]
[ 13465-09-3 ]
[ 244187-81-3 ]
C₃H₃N₂(C₆H₃(CH(CH₃)2)2)2⁽¹⁺⁾*[InBr₄]^(1-)*0.5(C₂H₅)2O [ No CAS ]

Reference： [1]Journal of Organometallic Chemistry,2002,vol. 656,p. 203 - 210

9
[ 13465-09-3 ]
[ 244187-81-3 ]
[ 478971-11-8 ]

Reference： [1]Journal of Organometallic Chemistry,2002,vol. 656,p. 203 - 210

10
[ 1295-35-8 ]
[ 2687-12-9 ]
[ 244187-81-3 ]
[Ni(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)(cin)Cl] [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2003,vol. 125,p. 872 - 873
[2]Chemistry - A European Journal,2014,vol. 21,p. 3906 - 3909

11
[ 1295-35-8 ]
[ 107-05-1 ]
[ 244187-81-3 ]
(IPr)Ni(π-allyl)Cl [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2003,vol. 125,p. 872 - 873
[2]Angewandte Chemie - International Edition,2017,vol. 56,p. 9048 - 9052
Angew. Chem.,2017,vol. 129,p. 9176 - 9180,5

12
bis(η3-allyl-μ-chloropalladium(II)) [ No CAS ]
[ 244187-81-3 ]
allylchloro[1,3-bis(2,6-di-isopropylphenyl)imidazol-2-ylidine]palladium(II) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran; for 4h;	2,6-Diisopropylaniline (15 g, 84.7 mmol) was dissolved in 67 ml of 1-propanol and 15 in of water, after which glyoxal (40% aqueous solution, 5.6 g, 38.5 mmol) was added thereto. The reaction was carried out at 70 C. for 1 hour, the temperature was lowered to room temperature, and then the reaction product was filtered. The remaining solid was dissolved in methylene chloride, added with anhydrous magnesium sulfate and then filtered, after which the filtered solution was decompressed to a vacuum thus removing the solvent. The compound (5.048 g, 12.73 mmol) thus obtained and para-formaldehyde (0.458 g, 15.27 mmol) were dissolved in 83 ml of toluene and stirred at 100 C. for 2 hours. Thereafter, the temperature was lowered to 40 C., and hydrochloric acid (4 N, d=1.05 g/ml dioxane solution, 4.01 g, 15.27 mmol) was added thereto and thus the resulting precipitate was filtered. The solid compound thus obtained was dissolved in methylene chloride and dried over anhydrous magnesium sulfate, and the filtered solution was decompressed to a vacuum, thus removing the solvent. The compound (1.753 g, 4.124 mmol) thus obtained and potassium tert-butoxide (0.508 g, 4.537 mmol) were dissolved in 24 ml of THF and allowed to react with stirring for 4 hours. The solvent was removed using vacuum decompression, after which the product was dissolved in toluene and filtered using celite. The filtered solution was decompressed to a vacuum thus removing the solvent. The compound (1.335 g, 3.435 mmol) thus obtained and palladium allyl chloride (0.629 g, 3.435 mmol) were dissolved in 8 in of THF and stirred for 4 hours. The reaction solution was passed through silica gel and filtered, after which the solution was decompressed to a vacuum thus removing the solvent, giving the title compound of Formula 10 in which R1═R4=2,6-diisopropylphenyl; R2═R3═H; X1=allyl; X2═Cl.

Reference： [1]Organometallics,2005,vol. 24,p. 439 - 445
[2]Organometallics,2002,vol. 21,p. 5470 - 5472
[3]European Journal of Inorganic Chemistry,2013,p. 4958 - 4969
[4]Patent: JP5662491,2015,B2 .Location in patent: Paragraph 0120-0122

13
[ 1295-35-8 ]
[ 29046-78-4 ]
[ 244187-81-3 ]
[Ni(μ-Cl)(IPr)]₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53%	In toluene; at 20℃; for 18h;Glovebox; Inert atmosphere;	Inside an Argon-filled glovebox, Ni(dme)Cl2 (280 mg, 1.27 mmol, 1.0 equiv.), Ni(cod)2 (350 mg, 1.27 mmol, 1.0 equiv.) and <strong>[244187-81-3]IPr</strong> (990 mg, 2.50 mmol, 1.97 equiv.) were suspended in toluene (20 mL). The resulting mixture was stirred at ambient temperature inside the glovebox for 18 h. The obtained mixture was filtered through a small pad of Celite in a fritted funnel and the filtrate concentrated to 8 mL under reduced pressure. Pentane (32 mL) was added to and the mixture was cooled at -25 C overnight. The formed crystals were collected by filtration and washed with cold pentane (3 x 2 mL) to afford Ni(I) dimer 1 as greenish yellow crystals in 53% yield (660 mg, 0.68 mmol).

Reference： [1]Inorganic Chemistry,2005,vol. 44,p. 3774 - 3776
[2]Patent: WO2020/58505,2020,A1 .Location in patent: Page/Page column 20
[3]Organometallics,2022,vol. 41,p. 486 - 496

14
[ 29892-37-3 ]
[ 244187-81-3 ]
chloro(1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene)gold(I) [ No CAS ]

Reference： [1]Organometallics,2005,vol. 24,p. 2411 - 2418
[2]Angewandte Chemie - International Edition,2005,vol. 44,p. 5284 - 5288
[3]Inorganic Chemistry,2022,vol. 61,p. 357 - 367

15
[ 71564-36-8 ]
[ 244187-81-3 ]
tricarbonyl(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)nickel [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2005,vol. 127,p. 2485 - 2495

16
bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)] [ No CAS ]
[ 244187-81-3 ]
(3-phenylallyl)(chloro)-[1,3-bis(2,6-diisopropylphenyl)-4,5-dihydroimidazol-2-ylidene]palladium(II) [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2006,vol. 128,p. 4101 - 4111

17
bis[(1,2,3-η)-2-butenyl]di(μ-chloro)palladium(II) [ No CAS ]
[ 244187-81-3 ]
chloro(N,N'-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)(η3-1-methylallyl)palladium(II) [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2006,vol. 128,p. 4101 - 4111
[2]European Journal of Inorganic Chemistry,2013,p. 4958 - 4969

18
[ 12288-41-4 ]
[ 244187-81-3 ]
(N,N'-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)Pd(3,3-dimethylallyl)Cl [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2006,vol. 128,p. 4101 - 4111

19
[ 1109-15-5 ]
[ 244187-81-3 ]
[ 1082895-88-2 ]

Reference： [1]Angewandte Chemie - International Edition,2008,vol. 47,p. 7433 - 7437
[2]Angewandte Chemie - International Edition,2008,vol. 47,p. 7433 - 7437
[3]Dalton Transactions,2009,p. 7179 - 7188
[4]Inorganic Chemistry,2011,vol. 50,p. 7344 - 7359
[5]Inorganic Chemistry,2011,vol. 50,p. 7344 - 7359

20
[ 244187-81-3 ]
SiCl₂*NHC [ No CAS ]
[ 250285-32-6 ]

Reference： [1]Angewandte Chemie - International Edition,2009,vol. 48,p. 5683 - 5686
Angew. Chem., Int. Ed.,2009,vol. 121,p. 5793 - 5796

21
tetrachlorosilane [ No CAS ]
[ 244187-81-3 ]
[ 1070876-61-7 ]

Yield	Reaction Conditions	Operation in experiment
100%	In hexane; at 20℃;	Kuhn et al. synthesized hypervalent L':SiCl4 {where L': is :C[N(R)C(CH3)]2 and R is alkyl} complexes, which are neutral equivalents of [SiCl5]-. Consistently, we found that room-temperature reaction of a sterically demanding N-heterocyclic carbene ligand, R':, with SiCl4 in hexane, gives R'SiCl4, 7, in an essentially quantitative yield. The potassium graphite reduction of 7 (in a 1:KC8 ratio of 1:6) in hexane produced air-sensitive, orange-red, sheetlike crystals of 8(6.1% yield) and air-sensitive, dark red, block crystals of 9 (as a minor product) (FIG. 6). However, when the potassium graphite reduction of 7 is performed (with a 1:KC8 ratio of 1:4) in tetrahydrofuran (THF) (FIG. 1), compound 9 can be exclusively isolated and in higher yield (23.2%). In the 1H nuclear magnetic resonance (NMR) spectra, the imidazole resonances (in C6D6) of compounds 7, 8, and 9 appear at 6.40, 6.31, and 6.58 parts per million (ppm), respectively. The 1H-decoupled 29Si NMR spectra of compounds 7 to 9 were also determined. The 29Si NMR chemical shift of (in CD2Cl2), 108.9 ppm, is comparable to reported values (-104.7 to -105.9 ppm) of hypervalent Si compounds L':SiCl4 {where L': is :C[N(R)C(CH3)]2 and R is alkyl}. The 29Si NMR resonance of 8 (in C6D6), 38.4 ppm, compares with 78.3 ppm of [C(H)N(tBu)]2Si: and 14.6 ppm of [PhC(NtBu)2]SiCl, but is at a considerably lower field than the -48.6 to -57.4 ppm range of silylene-isocyanide complexes. The 29Si chemical shift of 3 (in C6D6), 224.5 ppm, resides at an even lower field than typical disilene resonances (50 to 155 ppm).

Reference： [1]Patent: US2010/41895,2010,A1 .Location in patent: Page/Page column 9

22
[ 13283-31-3 ]
[ 244187-81-3 ]
[ 956972-12-6 ]

Yield	Reaction Conditions	Operation in experiment
84%	In tetrahydrofuran; at 20℃; for 16h;Inert atmosphere; Schlenk technique;	To a dried Schlenk tube under argon was dissolved <strong>[244187-81-3]IPr</strong> carbene (800 mg, 2.05 mmol, 1.0 eq.)in THF (0.1 M), then BH3 (1M in THF, 2.15 mL, 2.15 mmol, 1.05 eq.) was added and themixture was stirred at room temperature for 16 hours. Solvent was removed in vacuo, and theresidue was purified by flash column chromatography (SiO2, pentane/AcOEt: 90/10) to affordI Pr-BH3 as a white solid (695 mg, 84 %). 1H NMR (400 MHz, THF-d8) δ 7.45 (dd, J = 8.3,7.2 Hz, 1H), 7.37 - 7.26 (m, 3H), 2.65 (quint, J = 6.9 Hz, 2H), 1.30 (d, J = 6.9 Hz, 6H), 1.20(d, J = 7.0 Hz, 6H). 13C NMR (101 MHz, THF-d8) δ 145.41, 135.00, 129.36, 123.38, 121.90,28.54, 23.65, 22.49. 11B NMR (128 MHz, THF-d8) δ -35.23.

Reference： [1]Journal of Organometallic Chemistry,2021,vol. 956
[2]Journal of the American Chemical Society,2010,vol. 132,p. 2350 - 2358

23
[ 244187-81-3 ]
[ 1213792-66-5 ]

Reference： [1]Chemistry - A European Journal,2010,vol. 16,p. 432 - 435

24
[ 244187-81-3 ]
[ 1228185-09-8 ]

Yield	Reaction Conditions	Operation in experiment
85%	With hexachloroethane; In tetrahydrofuran; at -40 - 23℃; for 24h;	Example 1.Preparation of Fluorinating ReagentsθCI A Bnew lluorinating reagentN, N'-l, 3-bis(2,6-diisopropylphenyl)-2,2-dicholoimidazolidene (A)To N,N'-l ,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene (1 1.6 g, 30.0 mmol, 1.00 equiv) in 200 mL of THF at -40 C was added 1 , 1 ,1 ,2,2,2-hexachloroethane (8.38 mg, 36.0 mmol, 1.20 equiv). The reaction mixture was warmed to 23 C and was stirred for 24 h. The reaction mixture was cooled to -40 C and filtered off and filter cake was washed with cold THF to afford 1 1.7 g of compound A as a colorless solid (85%).NMR Spectroscopy: NMR (500 MHz, CD3CN, 23 C, δ): 8.51 (s, 2H), 7.75 (t, J = 7.8 Hz, 2H), 7.56 (d, J = 7.8 Hz, 4H), 2.37 (m, 4 H), 1.31 (d, J = 6.8 Hz, 12H), 1.25 (d, J = 6.8 Hz, 12H). 13C NMR (500 MHz, CD3CN, 23 C, δ): 146.4, 133.8, 129.5, 127.8, 126.3, 1 18.3, 30.2, 24.3, 23.5.(See e.g., Mendoza-Espinosa et al., J. Am. Chem. Soc, 132:7264-7265 (2010)).

Reference： [1]Patent: WO2012/142162,2012,A2 .Location in patent: Page/Page column 20-21
[2]Journal of the American Chemical Society,2010,vol. 132,p. 7264 - 7265
[3]Organic Process Research and Development,2014,vol. 18,p. 1041 - 1044
[4]Organic Letters,2015,vol. 17,p. 544 - 547
[5]Organometallics,2018,vol. 37,p. 4753 - 4762

25
[ 244187-81-3 ]
[ 1228185-10-1 ]

Yield	Reaction Conditions	Operation in experiment
85%	With bromine; In toluene;Inert atmosphere; Schlenk technique; Glovebox;	To the solution of 0.776 g (2.0 mmol) <strong>[244187-81-3]IPr</strong> in toluene, 0.045mL Br2 (1.0 mmol) was added. The reaction mixture wasstirred for 6 h and then solvent was decanted and the whiteprecipitate was dried under vacuum. The recrystallization wasdone in acetonitrile. Yield: 0.470 g (85%). m.p. 225C; 1HNMR (400 MHz, DMSO-d6, ppm): 8.80 (s, 2H, -CH=CH-),7.70-7.60 (m, 6H, Ph), 2.20 (m, 4H, -CH-), 1.21 (d, J = 6.8Hz, 12H, -CH3), 1.17 (d, J = 6.9 Hz, 12H, -CH3); 13C NMR(101 MHz, DMSO-d6, ppm): 145.2, 133.1, 130.3, 128.3,128.0, 125.8, 29.5, 24.3, 23.4. MALDI MS: m/z 547.10 [M]+.

Reference： [1]Journal of the American Chemical Society,2010,vol. 132,p. 7264 - 7265
[2]Journal of the Indian Chemical Society,2018,vol. 95,p. 765 - 770

26
[ 244187-81-3 ]
[ 956972-12-6 ]

Reference： [1]Journal of Organic Chemistry,2010,vol. 75,p. 6983 - 6985
[2]European Journal of Inorganic Chemistry,2011,p. 3686 - 3689
[3]Journal of the American Chemical Society,2010,vol. 132,p. 2350 - 2358

27
[ 75-77-4 ]
[ 244187-81-3 ]
[ 1228185-20-3 ]

Reference： [1]Angewandte Chemie - International Edition,2015,vol. 54,p. 14075 - 14079
Angew. Chem.,2015,vol. 127,p. 14281 - 14285,5
[2]Journal of the American Chemical Society,2010,vol. 132,p. 14370 - 14372

28
[ 1295-35-8 ]
[ 79271-56-0 ]
[ 244187-81-3 ]
[(1,3-bis(2,6-di-isopropylphenyl)imidazol-2-ylidene)NiH]OTf [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		In some embodiments, the catalyst can be generatedas follow: 1 ,3-bis(2,6-di-isopropylphenyl)imidazol-2-ylidene (<strong>[244187-81-3]IPr</strong>) (0.05 mmol) and Ni(cod)2 (0.05 mmol) were added to an oven-dried test tube equipped with a stir bar in glove box. The tube was sealed with a septum, brought out of the glove box, and connected to a nitrogen line. The catalyst mixture was dissolved in degassed toluene (2 mL) under nitrogen and stirred at room temperature for 1 hout The 1-octene (10 mol %), triethylamine (0.3 mmol), p-anisaldehyde (0.05 mmol, 5 mol %), triethylsilyltriflate (0.1 mmol, 10 mol %) were then added sequentially to the reaction mixture,and the mixture was stirred for 15 mins at it.

Reference： [1]Angewandte Chemie - International Edition,2010,vol. 49,p. 9182 - 9186
[2]Patent: US2015/315169,2015,A1 .Location in patent: Paragraph 0094

29
[ 244187-81-3 ]
[ 1311297-12-7 ]

Reference： [1]Chemistry - A European Journal,2011,vol. 17,p. 5965 - 5971
[2]Journal of Organometallic Chemistry,2013,vol. 743,p. 44 - 48
[3]Chemical Communications,2018,vol. 54,p. 9753 - 9756
[4]Zeitschrift fur Anorganische und Allgemeine Chemie,2020,vol. 646,p. 574 - 579

30
[ 1295-35-8 ]
[ 111-66-0 ]
[ 79271-56-0 ]
[ 123-11-5 ]
[ 244187-81-3 ]
[ 930806-53-4 ]
[(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)NiH(OTf)] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		1,3-bis(2,6-di-isopropylphenyl)imidazol-2-ylidene (<strong>[244187-81-3]IPr</strong>) (0.05 mmol, 5 mol %) and Ni(cod)2 (0.05 mmol, 5 mol %) were added to an oven-dried test tube equipped with a stir bar in glove box. The tube was sealed with a septum, brought out of the glove box, and connected to a nitrogen line. The catalyst mixture was dissolved in degassed toluene (2 mL) under nitrogen and stirred at room temperature for 1 hour. The 1-octene (10 mol %), triethylamine (0.3 mmol), p-anisaldehyde (0.05 mmol, 5 mol %), triethylsilyltriflate (0.1 mmol, 10 mol %) were then added sequentially to the reaction mixture, and the mixture was stirred for 15 mins at rt.

Reference： [1]Patent: US2011/201840,2011,A1 .Location in patent: Page/Page column 7

31
[ 244187-81-3 ]
[ 905931-87-5 ]

Reference： [1]Angewandte Chemie - International Edition,2012,vol. 51,p. 11354 - 11357,4
Angewandte Chemie,2012,vol. 124,p. 11516 - 11519

32
[ 244187-81-3 ]
[ 1187680-47-2 ]

Reference： [1]Inorganic Chemistry,2015,vol. 54,p. 9611 - 9618
[2]Angewandte Chemie - International Edition,2013,vol. 52,p. 1801 - 1805
Angew. Chem.,2013,vol. 125,p. 1845 - 1850,6

33
[ 1428586-19-9 ]
[ 244187-81-3 ]
ClPd(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)(η¹-allenyl)(PMe3) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%		To a Schlenk flask containing 1 (0.170 g, 0.51 mmol) was added <strong>[244187-81-3]IPr</strong> (0.198 g, 9.51 mmol) dissolved in THF (6 ml). After stirring the reaction mixture for 3 h at room temperature, the solvent was completely removed. To the resulting oily residue was added a diethyl ether/n-hexane (3:1) solution and then stored in the freezer to give crude solids. The solids were filtered, washed with hexane (2 ml × 2), and recrystallized from diethyl ether to give white crystals of [ClPd(<strong>[244187-81-3]IPr</strong>)(CH=C=CH2)(PMe3)], (18, 0.291 g, 88%). Anal. Calc for C33H48ClN2PPd: C, 61.39; H, 7.49; N, 4.34. Found: C, 60.95; H, 7.94; N, 4.29%. IR (KBr, cm-1): ν(=C=) 1916. 1H NMR (300 MHz, CDCl3, δ): 1.10 (d, 2JHP = 9.5 Hz, 9H, P(CH3)3), 1.11 (d, 2JHH = 6.6 Hz, 12H, CH(CH3)2), 1.42 (d, 2JHH = 6.6 Hz, 12 H, CH(CH3)2), 3.13 (sep, 2JHH = 6.6 Hz, 4 H, CH(CH3)2), 3.63 (dd, 4JHH = 6.6 Hz, 5JHP = 3.3 Hz, 2H, =CH2), 4.54 (dt, 4JHH = 6.6 Hz, 3JHP = 2.2 Hz, 1H, =CH), 7.05 (d, 3JHH = 1.5 Hz, 2H, =CH), 7.28 (m, 3H, Ar-H), 7.44 (m, 3 H, Ar-H). 13C{1H} NMR (75 MHz, CDCl3, δ): 13.3 (d, 1JPC = 29 Hz, P(CH3)3), 23.2 (s, CH(CH3)2), 25.9 (s, CH(CH3)2), 28.6 (s, CH(CH3)2), 64.6 (s, =CH2), 77.9 (d, 2JPC = 9.9 Hz, Pd-CH), 123.5 123.6, 123.7, 129.4, 136.1, 145.9 (s, Ar), 181.7 (d, 2JPC = 168 Hz, NCN), 200.1 (d, 3JPC = 5.6 Hz, =C=). 31P{1H} NMR (120 MHz in CDCl3, δ): -15.0 (s).

Reference： [1]Inorganica Chimica Acta,2013,vol. 398,p. 54 - 63

34
[ 1428586-25-7 ]
[ 244187-81-3 ]
ClPd(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)(η¹-propargyl)(PMe3) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%		To a Schlenk flask containing complex 7 (0.224 g, 0.55 mmol) was added <strong>[244187-81-3]IPr</strong> (0.213 g, 0.55 mmol) in THF (5 ml). After stirring the reaction mixture for 3 h at room temperature, the solvent was completely removed. To the resulting oily residue was added a diethyl ether/n-hexane (2:4) solution and then stored in the freezer to give crude solids. The solids were filtered, washed with hexane (2 ml × 2), and recrystallized from (diethyl ether)/hexane to give yellow crystals of [ClPd(<strong>[244187-81-3]IPr</strong>)(CH2C≡CPh)(PMe3)], (19, 0.328 g, 83%). Anal. Calc. for C39H52ClN2PPd: C, 64.90; H, 7.27; N, 3.88. Found: C, 64.87; H, 7.68; N, 3.84%. IR (KBr, cm-1): ν(C≡C) 2184. 1H NMR (300 MHz, CDCl3, δ): 1.12 (d, 2JHH = 6.6 Hz, 12H, CH(CH3)2), 1.20 (d, 2JHP = 9.5 Hz, 9H, P(CH3)3), 1.44 (d, 2JHH = 6.6 Hz, 12H, CH(CH3)2), 1.46 (d, 3JHP = 5.5 Hz, 2 H, CH2), 2.88 (br, 4H, CH(CH3)2), 3.32 (br, 4H, CH(CH3)2), 7.03-7.38 (m, 11H, Ar-H). The 1H signal of CH in the heterocyclic ring was overlapped to the aromatic signals. 13C{1H} NMR (75 MHz, CDCl3, δ): -9.7 (d, 2JPC = 1.9 Hz, CH2), 12.9 (d, 1JPC = 27 Hz, P(CH3)3), 23.2 (s, CH2), 26.1 (s, CH(CH3)2), 28.7 (s, CH(CH3)2), 31.6 (s, CH(CH3)2), 78.7 (d, 3JPC = 3.7 Hz, C≡C-Ph), 98.5 (d, 4JPC = 2.7 Hz, C≡C-Ph), 123.6 123.7, 125.7, 126.5, 127.8, 129.6, 130.6, 130.7, 146.5 (s, Ar), 184.6 (d, 2JPC = 159 Hz, NCN). 31P{1H} NMR (120 MHz in CDCl3, δ): -13.2 (s).

Reference： [1]Inorganica Chimica Acta,2013,vol. 398,p. 54 - 63

35
[ 7550-45-0 ]
[ 244187-81-3 ]
[titanium(IV)tetrachloride(C₃H₂N₂(2,6-diisoprpylphenyl)2)] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
54%	In diethyl ether; at -78 - 25℃; for 48h;Inert atmosphere; Schlenk technique;	<strong>[244187-81-3]IPr</strong> [<strong>[244187-81-3]IPr</strong> = :C{N(2,6-iPr2C6H3)CH}2] (0.614 g, 1.580 mmol) was dissolved in diethyl ether (20 mL) and cooled to -78 C (Acetone/Liq N2 bath). TiCl4 (0.300 g, 1.580 mmol) was slowly added over a period of 5 min while stirring. The resulting mixture was warmed to room temperature and stirred for two days. After filtration, the solvent was evaporated under reduced pressure to remove the all volatiles, and the residue was extracted with dry toluene (8 mL). After cooling to -30 C for three days, the resulting yellow crystalline solid was isolated and dried in vacuum. Yield (0.490 g, 54%). M.p.: 218-220 C. 1H NMR (C6D6, 250 MHz, 25 C): δ = 7.26-7.13 (m, 6H, Ar CH), 6.57 (s, 2H, -C=CH), 3.21 (sept, 4H, 3JH-H = 6.8 Hz, CH(Me)2), 1.52 (d, 3JH-H = 6.7 Hz, 12H, CH3), 1.01 (d, 3JH-H = 6.7 Hz, 12H, CH3) ppm; 13C NMR (C6D6, 62.8952 MHz, 25 C): δ = 188.8 (C-Ti), 146.9 (C=C), 133.2 (C(Dipp)-N), 131.8 (o-C(Dipp)), 124.6 (m-C(Dipp)), 123.6 (p-C(Dipp)), 29.4 (CHMe2), 26.8 (CHMe2), 22.2 (CHMe2). IR (ν, cm-1): 2939 (s), 2904 (w), 2846 (w), 1526 (s), 1449(s), 1375 (w), 1354 (w), 1318 (s), 1190 (s), 1173 (w), 1091 (s), 1050 (vs), 965 (w), 927 (w), 795 (vs), 746 (vs), 672(s), 509 (s), 430 (vs). Elemental analysis calc. (%) for C27H36N2Cl4Ti (576.11 g/mol): C, 56.23, H, 6.29, N, 4.86. Found: C, 56.13; H, 7.14; N, 4.72%.

Reference： [1]Polyhedron,2013,vol. 52,p. 1103 - 1108

36
[ 7550-45-0 ]
[ 244187-81-3 ]
[titanium(IV)tetrachloride(C₃H₂N₂(2,6-diisoprpylphenyl)2)2] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
28%	at -78 - 25℃; for 60h;Inert atmosphere; Schlenk technique;	Compound 1 (3.00 g, 7.726 mmol) was dissolved in diethyl ether (50 mL) and cooled to -78 C (Acetone/Liq N2 bath). To this stirred solution TiCl4 (0.732 g, 3.860 mmol) was slowly added through a syringe. The resultant mixture was warmed to room temperature and stirred for 60 h. After removal of all volatiles in vacuum the solid residue was extracted with THF (20 mL) and the resulting solution was cooled to -30 C for three days to give bright yellow crystals of 3 which were filtered and quickly washed with cold n-hexane (5 × 2 mL) and dried under vacuo. Yield (1.04 g, 28%). M.p.: 162 C (dec.). 1H NMR (C6D6, 250 MHz, 25 C): δ = 7.23-7.12 (m, 6H, Ar-CH), 6.42 (s, 4H, -C=CH), 3.14 (sept, 8H, 3JH-H = 6.7 Hz, CH(Me)2), 1.41 (d, 3JH-H = 6.6 Hz, 24H, CH3), 0.98 (d, 3JH-H = 6.8 Hz, 24H, CH3) ppm; 13C NMR (C6D6, 62.8952 MHz, 25 C): δ = 193.1 (C-Ti), 146.4 (C=C), 137.3 (C(Dipp)-N), 129.3 (o-C(Dipp)), 123.5 (m-C(Dipp)), 122.5 (p-C(Dipp)), 28.8 (CHMe2), 26.3 (CHMe2), 23.1 (CHMe2). IR (ν, cm-1): 2939 (vs), 2905 (w), 2843 (w), 1520 (vw), 1451 (s), 1373 (s), 1350 (w), 1318 (s), 1226 (w), 1106 (w), 1091 (w), 1052 (s), 930 (s), 795 (vs), 750 (vs), 689 (s), 628 (w), 504 (w), 432 (w). Elemental analysis calc. (%) for C54H72N4TiCl4 (966.854 g/mol): C, 67.08; H, 7.50; N, 5.79. Found: C, 66.47; H, 7.90; N, 5.76%

Reference： [1]Polyhedron,2013,vol. 52,p. 1103 - 1108

37
[ 7783-63-3 ]
[ 244187-81-3 ]
[titanium(IV)tetrafluoride(C₃H₂N₂(2,6-diisoprpylphenyl)2)2] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
43%	In tetrahydrofuran; at -78 - 25℃; for 20h;Inert atmosphere; Schlenk technique;	TiF4 (0.500 g, 4.036 mmol) in THF (10 mL) was added to a stirred solution of <strong>[244187-81-3]IPr</strong> [<strong>[244187-81-3]IPr</strong> = : C{N(2,6-iPr2C6H3)CH}2] (3.13 g, 8.073 mmol) in THF (15 mL) at -78 C. The brown reaction mixture was stirred for additional one hour at -78 C and then allowed to warm to room temperature. After stirring for 20 h, the reaction mixture was filtered, concentrated to 20 mL and stored at -30 C overnight. The colorless crystals formed were filtrated, washed with cold n-hexane (5 × 2 mL) and dried under reduced pressure to get 4 as a white solid. Further crystallization of the filtrate at -30 C for four days gave a second crop of crystals. Overall yield (1.57 g, 43% with respect to TiF4). M.p.: 237 C (dec). 1H NMR (C6D6, 250 MHz, 25 C): δ = 7.35-7.29 (2H, m, Ar CH), 7.13-7.18 (4H, m, Ar CH), 6.34 (s, 2H, -C=CH), 2.78 (s, 4H, 3JH-H = 6.6 Hz, CH(Me)2), 1.25 (d, 3JH-H = 6.6 Hz, 12H, CH3), 1.07 (d, 3JH-H = 6.6 Hz, 12H, CH3) ppm; 13C NMR (C6D6, 62.8952 MHz, 25 C): δ = 188.5 (quintet, 2JC-F = 6.8 Hz, C-Ti), 146.3 (C=C), 136.5 (C(Dipp)-N), 129.1 (o-C(Dipp)), 123.0 (m-C(Dipp)), 122.5 (p-C(Dipp)), 28.8 (CHMe2), 25.9(CHMe2), 22.9 (CHMe2). 19F NMR (C6D6, 235.357 MHz): δ = 169.76 (s) ppm. IR (ν, cm-1): 2938 (s), 2904(w), 2845(w), 1526(w), 1445(s), 1388(w), 1374(w), 1352(w), 1319(s), 1265(w), 1246(w), 1193(w), 1171(s), 1096(s), 1051(s), 939 (w), 930(w), 794(vs),749(vs), 689(w), 673(s), 616(vs), 430(w). Elemental analysis calc. (%) for C54H72N4F4Ti (901.103 g/mol): C, 71.98; H, 8.05; N, 6.21. Found: C, 71.74; H, 7.07; N, 6.42%.

Reference： [1]Polyhedron,2013,vol. 52,p. 1103 - 1108

38
[ 109-99-9 ]
[ 7646-85-7 ]
[ 244187-81-3 ]
[zinc(II)dichloride(C₃H₂N₂(2,6-diisoprpylphenyl)2)(tetrahydrofuran)] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	at 25℃; for 24h;Inert atmosphere; Schlenk technique;	Method B: A Schlenk tube containing both ZnCl2 (0.300 g, 2.202 mmol) and <strong>[244187-81-3]IPr</strong> (0.855 g, 2.202 mmol), THF was added (8 mL). The resultant reaction mixture became clear and the formation of a white precipitate was observed after 15 min stirring at room temperature. The suspension was then stirred at room temperature for 24 h, after which the white precipitate was filtered, washed with n-hexane (2 × 4 mL) and dried in vacuum to give 5 as a white powder. Yield: 225 mg (19%). After evaporation of the solvent of the filtrate, extraction of the residual solid with benzene and removal of the benzene in vacuum, a second batch of product was obtained (630 mg). Overall yield: 0.855 g (74%). M.p.: 280 C (dec). 1H NMR (C6D6, 250 MHz, 25 C): δ = 7.25-7.20 (m, 4H, Ar-CH), 7.13 (m, 2H, Ar-CH), 6.46 (s, 2H, -C=CH), 2.88 (sept, 4H, 3JH-H = 6.7 Hz, CH(Me)2), 1.54 (d, 3JH-H = 6.1 Hz, 12H, CH3), 1.00 (d, 3JH-H = 6.7 Hz, 12H, CH3) ppm; 13C NMR (C6D6, 62.8952 MHz, 25 C): δ = 176.4 (C-Zn), 146.2 (C=C), 134.6 (C(Dipp)-N), 130.8 (o-C(Dipp)), 124.5 (m-C(Dipp)), 124.2 (p-C(Dipp)), 29.0 (CHMe2), 26.1 (CHMe2), 23.4 (CHMe2) ppm. IR (ν, cm-1): 2937 (vs), 2906 (w), 2845 (w), 1581 (s), 1541 (s), 1456 (s), 1446 (w), 1261 (w), 1171 (w), 1110 (s), 1098 (w), 1035 (w), 941 (w), 927 (w), 793 (vs), 749 (vs), 695 (w), 629 (w), 451 (w). Elemental analysis calc. (%) for C27H36N2Cl2Zn (524.88 g/mol): C, 61.78; H, 6.91; N, 5.33. Found: C, 61.23; H, 7.11; N, 5.40%.

Reference： [1]Polyhedron,2013,vol. 52,p. 1103 - 1108

39
[ 77066-67-2 ]
[ 244187-81-3 ]
C₂₇H₃₉N₂Si⁽¹⁺⁾*CF₃O₃S^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
2.5 g	In toluene; at 0 - 20℃;Inert atmosphere; Schlenk technique;	To phenylsilane (0:62 mL, 97%, d = 0:88 g mL-1, 4:9 mmol) was added dropwise trifluoromethanesulfonic acid (0:44 mL, 98%, d = 1:71 g mL-1, 4:9 mmol) at 50 C under stirring. After 10 min a solution of NHC (1:90 g, 4:9 mmol) in toluene (50 mL) was added in situ into the solution of produced H3Si(OTf). A colorless precipitate was formed immediately. The solvent toluene was replaced by dichloromethane, from which compound 4 crystallized as colorless plates with a yield of 2:5 g(4:4 mmol, 90%).

Reference： [1]Zeitschrift fur Naturforschung, B: Chemical Sciences,2013,vol. 68,p. 445 - 452

40
[ 244187-81-3 ]
C₂₇H₃₈Cl₂N₂Si [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With Dichlorosilane; In toluene; at -10 - 20℃; for 0.5h;Inert atmosphere; Schlenk technique;	A molar excess of SiH2Cl2 was introduced into the solution of NHC (0:63 g, 1:6 mmol) in toluene (20 mL) at -10 C. The reaction mixture was allowed to warm to room temperature and stirred at room temperature for 30 min.The excess of SiH2Cl2 and the solvent were evaporated in a vacuum, and the residue was washed with n-hexane (5 mL) and extracted with toluene to afford compound 1 with a yield of 0.67 g (85%).

Reference： [1]Zeitschrift fur Naturforschung, B: Chemical Sciences,2013,vol. 68,p. 445 - 452

41
copper(l) chloride [ No CAS ]
[ 244187-81-3 ]
[ 578743-87-0 ]

Yield	Reaction Conditions	Operation in experiment
45%	With sodium t-butanolate; In tetrahydrofuran; at 30℃; for 2h;Inert atmosphere;	General procedure: To a stirred solution of imidazolium salts (0.045 mmol), NaOtBu (4.3 mg, 0.045 mmol) and CuCl (4.5mg, 0.045 mmol) was added THF (0.5 mL, 0.09 M) at 30 oC under argon atmosphere. After stirring for 2 h, the solution of K+[CF3B(OMe)3]- (63.5 mg, 0.3 mmol, 6.0 equiv) in DMF (0.5 mL) was added dropwise. Then the mixture was kept stirring at 30 oC for 10 h. After that, the reaction was quenched with water. Aqueous layer was extracted with EtOAc (15 mL x 3), and the combined organic layers was washed with brine, dried over Na2SO4 and concentrated under reduced pressure. Then the crude product was purified by column chromatography on silica gel to give the imidazolinone 3b-d.

Reference： [1]Journal of Organometallic Chemistry,2013,vol. 743,p. 44 - 48

42
C₁₄H₁₁Cl₂FeN₂Pd [ No CAS ]
[ 244187-81-3 ]
C₄₁H₄₇ClFeN₄Pd [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2014,vol. 12,p. 3114 - 3122

43
C₃₈H₂₆Br₂Cl₂Fe₂N₂Pd₂ [ No CAS ]
[ 244187-81-3 ]
C₄₆H₄₉BrClFeN₃Pd [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With potassium tert-butylate; In tetrahydrofuran; at 20℃; for 3h;Schlenk technique; Inert atmosphere;	General procedure: A Schlenk tube was charged with the above dimer (0.5 mmol),the corresponding imidazolium salt (1.2 mmol) and KtOBu(2.0 mmol) under nitrogen. Dry THF was added by a cannula andthe solution was stirred for 3 h at rt. The product was separatedby passing through a short silica gel column with CH2Cl2 as eluent,the second band was collected and afforded the correspondingNHC-palladacycles 2 and 3.

Reference： [1]Inorganica Chimica Acta,2014,vol. 423,p. 11 - 15

44
[ 766-08-5 ]
[ 557-20-0 ]
[ 244187-81-3 ]
[(IPr)ZnH(μ-H)]₂ [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2014,vol. 53,p. 9347 - 9351,5
Angew. Chem.,2014,vol. 126,p. 9501 - 9505,5
Angewandte Chemie,2014,vol. 126,p. 9501 - 9505,5

45
[ 1295-35-8 ]
C₈H₁₇F₃O₃SSi [ No CAS ]
[ 244187-81-3 ]
[(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)NiH(OTf)] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		(a) [NHC-NiH(OTf)] catalyst generation.In a glove box, Ni(cod)2 (0.05 mmol) and <strong>[244187-81-3]IPr</strong> or S<strong>[244187-81-3]IPr</strong> or IMes (0.05 mmol) wereadded to an oven-dried test tube equipped with a stir bar. After being sealed with aseptum and brought out of the glove box, the tube was connected to a N2 line. Themixture was dissolved in dried degassed toluene (2 mL, or indicated amount) andstirred at r.t. for 1 h. 1-octene (0.2 mmol), NEt3 (0.3 mmol), p-anisaldehyde (0.05mmol), and TESOTf (0.1 mmol) were then added sequentially and stirred for 45 minsat r.t.

Reference： [1]Synlett,2014,vol. 25,p. 2738 - 2742

46
C₃₄H₄₇BrNO₂PRu [ No CAS ]
[ 244187-81-3 ]
C₄₃H₅₀BrN₃O₂Ru [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40.4%	In hexane; at 50℃; for 17h;Inert atmosphere;	200 mg of complex (3b)-PCy3 and 160 mg of <strong>[244187-81-3]IPr</strong> were dissolved in 15 mL of anhydrous hexane and the solution was stirred at 50C for 17 hours. Afterwards the solution was cooled to room temperature and the obtained precipitate was filtrated and washed three times with 3 mL hexane. After drying, 90 mg of yellow solid was obtained. The yield was 40.4%. The reaction was completely conducted under inert gas protection.

Reference： [1]Patent: WO2014/198658,2014,A1 .Location in patent: Page/Page column 53

47
C₃₄H₄₈NO₂PRu [ No CAS ]
[ 244187-81-3 ]
C₄₃H₅₁N₃O₂Ru [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69.8%	In hexane; at 50℃; for 17h;Inert atmosphere;	200 mg of complex (3a)-PCy3 and 183 mg of <strong>[244187-81-3]IPr</strong> were dissolved in 15 mL of anhydrous hexane and the solution was stirred at 50C for 17 hours. Afterwards the solution was cooled to room temperature and the obtained precipitate was filtrated and washed three times with 3 ml . hexane. After drying, 160 mg of yellow solid was obtained. The yield was 69.8%. The reaction was completely conducted under inert gas protection.

Reference： [1]Patent: WO2014/198658,2014,A1 .Location in patent: Page/Page column 51

48
C₃₈H₂₆Br₂Cl₂Fe₂N₂Pd₂ [ No CAS ]
[ 244187-81-3 ]
C₄₆H₄₉BrClFeN₃Pd [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With potassium tert-butylate; In tetrahydrofuran; at 20℃; for 3h;Schlenk technique; Inert atmosphere;	General procedure: A Schlenk tube was charged with the above dimer (0.5 mmol),the corresponding imidazolium salt (1.2 mmol) and KtOBu(2.0 mmol) under nitrogen. Dry THF was added by a cannula andthe solution was stirred for 3 h at rt. The product was separatedby passing through a short silica gel column with CH2Cl2 as eluent,the second band was collected and afforded the correspondingNHC-palladacycles 2 and 3. (2): Red solid, yield 89%. Anal. Calc.for C40H37BrClFeN3Pd: C, 57.37; H, 4.45; N, 5.02. Found: C, 57.52;H, 4.26; N, 5.15%. IR (KBr, cm1): 2916, 1592, 1548, 1480, 1402,1321, 1103, 1018, 920, 731. 1H NMR (400 MHz, CDCl3): d 9.36(s, 1H, ArH), 7.79 (d, 1H, ArH), 7.66 (s, 1H, ArH), 7.59 (m, 1H,ArH), 7.07-7.22 (m, 5H, ArH), 6.85 (s, 1H, ArH), 6.71 (s, 1H, ArH),4.59 (s, 1H, C5H3), 4.20 (s, 1H, C5H3), 3.97 (s, 1H, C5H3), 3.43 (s,5H, C5H5), 2.91 (s, 3H, CH3), 2.52 (s, 3H, CH3), 2.35 (s, 6H, CH3),2.17 (s, 3H, CH3), 1.92 (s, 3H, CH3). (3): Red solid, yield 88%. Anal.Calc. for C46H49BrClFeN3Pd: C, 59.95; H, 5.36; N, 4.56. Found: C,60.12; H, 5.18; N, 4.73%. IR (KBr, cm1): 2957, 1589, 1547, 1462,1361, 1329, 1259, 1103, 1040, 920, 819, 810, 699. 1H NMR(400 MHz, CDCl3): d 9.51 (s, 1H, ArH), 7.79 (d, 1H, ArH), 7.68 (s,1H, ArH), 7.47-7.55 (m, 4H, ArH), 7.18-7.26 (m, 5H, ArH), 7.15(d, 1H, ArH), 4.95-5.02 (m, 1H, CH), 4.56 (s, 1H, C5H3), 4.25(s, 1H, C5H3), 3.89 (s, 1H, C5H3), 3.27 (m, 6H, C5H5+CH), 2.87-2.98 (m, 2H, CH), 1.84 (d, 3H, CH3), 1.61 (d, 3H, CH3), 1.52 (d, 3H,CH3), 1.45 (d, 3H, CH3), 1.25 (d, 3H, CH3), 1.08 (d, 3H, CH3), 0.83(s, 3H, CH3), 0.62 (s, 3H, CH3).

Reference： [1]Inorganica Chimica Acta,2014,p. 11 - 15

49
[ 244187-81-3 ]
C₂₇H₃₆N₃O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	With nitrogen(II) oxide; In toluene; at 23 - 78℃; for 1h;Glovebox; Inert atmosphere;	In a glove box maintaining a nitrogen atmosphere, A 40 mL vial was charged with 25 mL of toluene1,3-bis- (2,6-diisopropylphenyl) imidazolylidene (<strong>[244187-81-3]IPr</strong> (1a), 1.00 g, 2.57 mmol, 1.00 equiv) the solution was heated to 78 C.Nitric oxide (1.00 equiv) was supplied to the solution in gaseous form over several times, and a colorless solution turned dark brown. The solution was heated to 23 C and reacted for 1 hour. The solvent was removed in vacuo and the resulting solid suspended in 5 mL of ether (Et2O), then filtered and washed with ether (3 x 1 mL). And then vacuum dried to give a light orange solid (560 mg). The solidAt 30 CLeft for 48 hoursObtain a brown solid,It was washed with ether (Et2O) (3 x 0.5 mL)And dried under vacuum to give the desired compound (2a). (172 mg, yield = 68%).

Reference： [1]Journal of the American Chemical Society,2015,vol. 137,p. 4642 - 4645
[2]Patent: KR2019/11615,2019,A .Location in patent: Paragraph 0082-0088

50
C₁₈H₁₄Cl₂Pd₂ [ No CAS ]
[ 244187-81-3 ]
C₃₆H₄₃ClN₂Pd [ No CAS ]

Reference： [1]ACS Catalysis,2015,vol. 5,p. 3680 - 3688

51
C₂₀H₁₈Cl₂Pd₂ [ No CAS ]
[ 244187-81-3 ]
C₃₇H₄₅ClN₂Pd [ No CAS ]

Reference： [1]ACS Catalysis,2015,vol. 5,p. 3680 - 3688

52
C₂₄H₂₆Cl₂Pd₂ [ No CAS ]
[ 244187-81-3 ]
C₃₉H₄₉ClN₂Pd [ No CAS ]

Reference： [1]ACS Catalysis,2015,vol. 5,p. 3680 - 3688

53
[Pd(η³-tBu-indenyl)(μ-Cl)]₂ [ No CAS ]
[ 244187-81-3 ]
(IPr)Pd(1-t-Bu-indenyl)Cl [ No CAS ]

Reference： [1]ACS Catalysis,2015,vol. 5,p. 3680 - 3688

54
di(rhodium)tetracarbonyl dichloride [ No CAS ]
[ 244187-81-3 ]
cis-[(N,N-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)dicarbonylchlororhodium(I)] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	In toluene; for 12h;Inert atmosphere;	This procedure is a modified version of what was previously published [22] . To [Rh(CO)2Cl]2 (25 mg, 0.064 mmol) in 5 mL of toluene was added dropwise a solution of <strong>[244187-81-3]IPr</strong> (50 mg, 0.12 mmol) in 5 mL of toluene. After combining the reagents, the resulting mixture was stirred for 12 h. After this time a precipitate of <strong>[244187-81-3]IPr</strong>CH2·RhCl(CO)2 was formed and was separated from the mother liquor. The product was dried under vacuum and X-ray quality crystals were subsequently obtained by cooling a solution of <strong>[244187-81-3]IPr</strong>·RhCl(CO)2 in hexanes and dichloromethane to -35 C. The resulting NMR spectra were consistent with previously reported data [22] for this product (27mg, 73%). 1H NMR (498.1MHz, CDCl3): δ=1.28 (d, 3JHH=7.0Hz, 12H, CH(CH3)2), 1.39 (d, 3JHH=6.5Hz, 12H, CH(CH3)2), 2.90 (septet, 3JHH=7.0Hz, 4H, CH(CH3)2), 7.18 (s, 2H, N-CH-), 7.32 (d, 3JHH=8.0Hz, 4H, ArH), 7.50 (t, 3JHH=7.0Hz, 2H, ArH); 13C{1H} NMR (125.7MHz, CDCl3): δ=22.7 (CH(CH3)2), 26.4 (CH(CH3)2), 28.8 (CH(CH3)2), 124.1 (ArC), 124.7 (-NCH-), 130.4 (ArC), 135.0 (ArC), 180.2 (d, 1JCRh=45.5Hz,N-C-N), 183.0 (d, 1JCRh=73.5Hz, CO), 184.7 (d, 1JCRh=54.4Hz, CO); IR (Nujol, cm-1): 2073 (νCO) and 1990 (νCO).

Reference： [1]Polyhedron,2016,vol. 108,p. 8 - 14

55
[ 244187-81-3 ]
[ 2344-80-1 ]
[ 1315461-59-6 ]

Yield	Reaction Conditions	Operation in experiment
79%	In toluene; at 20℃; for 168h;Inert atmosphere;	To <strong>[244187-81-3]IPr</strong> (5.510 g, 14.18 mmol) dissolved in 150 mL of toluene was added ClCH2Si(CH3)3 (8.300 g, 67.93 mmol). After 168 h of stirring a small amount of precipitate formed and the mixture was filtered through a pad of Celite. The volatiles were then removed from the filtrate under vacuum to yield <strong>[244187-81-3]IPr</strong>CH2 as a spectroscopically pure off-white solid (4.511 g, 79%). 1H NMR (498.1 MHz, C6D6): δ = 1.22 (d, 3JHH = 6.9 Hz, 12H, CH(CH3)2), 1.36 (d, 3JHH = 6.9 Hz, 12H, CH(CH3)2), 2.42 (s, 2H, =CH2), 3.35 (septet, 3JHH = 6.9 Hz, 4H, CH(CH3)2), 5.85 (s, 2H, N-CH-), 7.17 (d, 3JHH = 7.0 Hz, 4H, ArH), 7.22 (t, 3JHH = 7.0 Hz, 2H, ArH); 13C{1H} NMR (125.7 MHz, C6D6): δ = 23.8 (CH(CH3)2), 24.3 (CH(CH3)2), 28.8 (CH(CH3)2), 44.3 (=CH2), 114.6 (-NCH-), 124.5 (ArC), 129.3 (ArC), 134.9 (ArC), 148.9 (ArC), 152.5 (N-C-N).

Reference： [1]Polyhedron,2016,vol. 108,p. 8 - 14

56
[ 1295-35-8 ]
[ 244187-81-3 ]
[ 386742-84-3 ]

Yield	Reaction Conditions	Operation in experiment
	In diethyl ether; at 20℃;Inert atmosphere;	Method A: Bis(1,5-cyclooctadiene)nickel(0) (0.50 g, 1.82 mmol) was dissolved in diethyl ether (20 mL). A solution of <strong>[244187-81-3]IPr</strong> (1.41 g, 3.64 mmol) in diethyl ether (20 mL) was slowly added at room temperature. A very dark purple colored solution was obtained. After the mixture was stirred overnight the volatiles were removed under reduced pressure. The solid was dissolved in 10 mL of n-pentane and cooled at -35 C to give a mixture of 1-<strong>[244187-81-3]IPr</strong> and starting materials. Spectroscopic characterization matched the previously reported data

Reference： [1]Journal of Organometallic Chemistry,2016,vol. 813,p. 46 - 54

57
[ 39716-73-9 ]
[ 244187-81-3 ]
trans-(1,3-bis(2,6-diisopropylphenyl)imidazolin-2-yliden)2NiCl2 [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	In tetrahydrofuran; at 20℃; for 12h;Inert atmosphere;	Bis(triphenylphosphine)nickel(II)dichloride (1.00 g, 1.53 mmol) was suspended in thf (20 mL). A solution of <strong>[244187-81-3]IPr</strong> (1.19 g, 3.06 mmol) in thf (20 mL) was slowly added at room temperature. Upon addition the blue suspension became a light pink suspension, which was stirred for an additional 12 hours. The pale pink solid was filtered and washed with warm thf (2 x 20mL). The solids of 2 were then dried under vacuum for 2 hours. Yield: 1.31 g, 95 %. Spectroscopic characterization matched the previously reported data.

Reference： [1]Journal of Organometallic Chemistry,2016,vol. 813,p. 46 - 54

58
[ 90624-27-4 ]
[ 244187-81-3 ]
(η3-Ind)Pd(1,3-bis(2,6-diisopropylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene)Cl [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	In diethyl ether; for 1.5h;Schlenk technique;	(r3-indenyl)2(ji-Cl)2Pd2 (3a) (0.600 g, 1.17 mmol) and <strong>[244187-81-3]IPr</strong> (0.900 g, 2.34 mmol) were added to a 100 mL Schlenk flask. Diethyl ether (40 mL) was added to the flask via cannula. The resulting solution was stirred for 90 minutes, during which time the reaction mixture became homogeneous. The solution was passed through a pad of silica gel, followed by the removal of solvent using a rotary evaporator to give 4a-<strong>[244187-81-3]IPr</strong> as an orange powder.Yield: 1.33 g, 88%. The ‘H NMR data was consistent with that published in the literature (Bielinski, et al., 2013, Organomet. 32:4025).

Reference： [1]Patent: WO2016/57600,2016,A1 .Location in patent: Page/Page column 38; 39

59
C₂₀H₁₈Cl₂Pd₂ [ No CAS ]
[ 244187-81-3 ]
C₃₇H₄₅ClN₂Pd [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	In diethyl ether; for 1.5h;Schlenk technique;	(r3-1-Me-indenyl)2(ji-Cl)2Pd2 (3b) (0.300 g, 0.502 mmol) and <strong>[244187-81-3]IPr</strong> (0.3 90 g,1.00 mmol) were added to a 100 mL Schlenk flask. Diethyl ether (30 mL) was added to theflask via cannula. The resulting solution was stirred for 90 minutes, during which time the reaction mixture became homogeneous. The solution was passed through a pad of silica gel, followed by the removal of solvent using a rotary evaporator to give 4b-<strong>[244187-81-3]IPr</strong> as an orange powder. Yield: 0.550 g, 81%. X-ray quality crystals were grown by slow evaporation from asaturated pentane solution.‘H NMR (C6D6, 600 MHz): 7.22 (t J = 7.6 Hz, 2H,para-HArjpr), 7.11 (d, J =6.5 Hz, 2H, meta-HArjpr), 7.07 (d, J = 7.3 Hz, 2H, meta-HArjpr), 6.81 (t, J = 8.0 Hz, 1H,md), 6.77 (t, J = 7.7 Hz, 1H, md), 6.41 (t, J = 8.1 Hz, 1H, md), 6.03 (br, 1H, md) 5.87 (d, J =7.1 Hz, 1H, md), 5.21 (br, 1H, md), 3.39 (sept, J = 6.8 Hz, 2H, (CH3)2C1]), 2.83 (sept, J = 6.8Hz, 2H, (CH3)2Cfl), 1.58 (s, 3H, CH3-Ind), 1.48 (d, J = 6.6 Hz, 6H, (CH3)2CH), 1.19 (d, J =6.6 Hz, 6H, (CH3)2CH), 1.06 (d, J = 6.7 Hz, 6H, (CH3)2CH), 0.93 (d, J = 6.7 Hz, 6H,(CH3)2CH). ‘3C{’H} NMR (C6D6, 150 MHz): 179.9, 146.6, 140.0, 138.4, 137.1, 130.5,125.5, 124.9, 124.8, 124.6, 117.0, 116.1, 110.1, 101.0, 66.1, 29.1, 29.0, 26.7, 26.0, 24.1, 22.9,12.4. Anal. Calcd for C37H45C1N2Pd: C, 67.37; H, 6.88; N, 4.25. Found: C, 67.15; H, 7.00;N, 4.27.

Reference： [1]Patent: WO2016/57600,2016,A1 .Location in patent: Page/Page column 39

60
C₂₄H₂₆Cl₂Pd₂ [ No CAS ]
[ 244187-81-3 ]
C₃₉H₄₉ClN₂Pd [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	In diethyl ether; for 1.5h;Schlenk technique;	(i3-1-’Pr-indenyl)2(ji-Cl)2Pd2 (3c) (0.300 g, 0.502 mmol) and <strong>[244187-81-3]IPr</strong> (0.3 90 g, 1.00 mmol) were added to a 100 mL Schlenk flask. Diethyl ether (30 mL) was added to theflask via cannula. The resulting solution was stirred for 90 minutes, during which time the reaction mixture became homogeneous. The solution was passed through a pad of silica gel, followed by the removal of solvent using a rotary evaporator to give 4c-<strong>[244187-81-3]IPr</strong> as an orange powder. Yield: 0.5 50 g, 81%. X-ray quality crystals were grown by slow evaporation from a saturated pentane solution.‘HNMR(C6D6, 600 MHz): 7.25 (t, J = 7.7 Hz, 2H,para-HArjpr), 7.15 (obscured by solvent, 2H, meta-HArjpr), 7.09 (dd, J = 1.4, 6.3 Hz, 2H, meta-HArjpr), 6.89 (d,7.4 Hz, 1H, md), 6.83 (t, J = 8.4 Hz, 1H, md), 6.55 (s, 2H, HCCH), 6.42 (t, J = 7.4 Hz,md), 6.05 (d, J = 2.7 Hz, 1H, md), 5.89 (d, J = 7.4 Hz, 1H, md), 5.29 (d, J = 2.8Hz, 1H,3.36 (sept, J = 6.8 Hz, 2H, (CH3)2C1]), 2.86 (sept, J = 6.8 Hz, 1H, (CH3)2CH-Ind), 2.82 (sept, J = 6.8 Hz, 2H, (CH3)2C1]), 1.48 (d, J = 6.7 Hz, 2H, (CH3)2CH), 1.19 (d, J = 6.9 Hz,(CH3)2CH), 1.18 (d, J = 5.2 Hz, 3H, (CH3)2CH-Ind), 1.16 (d, J = 4.5 Hz, 3H, (CH3)2CH- md), 1.06 (d, J = 6.8 Hz, 6H, (CH3)2CH), 0.93 (d, J = 6.8 Hz, 6H, (CH3)2CH). ‘3C{’H} NMR(C6D6, 150 MHz): 179.6, 146.8, 146.7, 138.1, 137.2, 137.0, 130.3, 125.1, 125.0, 124.8,124.6, 124.5, 117.4, 116.5, 110.5, 105.2, 67.4, 29.2, 29.1, 26.8, 26.0, 24.1, 22.9, 22.1, 21.0. Anal. Calcd for C39H49C1N2Pd: C, 68.11; H, 7.18; N, 4.07. Found: C, 67.89; H, 7.42; N,4.04.

Reference： [1]Patent: WO2016/57600,2016,A1 .Location in patent: Page/Page column 39; 40

61
η³-1-tert-butylindenyl palladium chloride dimer [ No CAS ]
[ 244187-81-3 ]
[(η³-1-^tBu-indenyl)Pd(1,3-bis(2,6-diisopropylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene)(Cl)] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	In diethyl ether; for 2h;Schlenk technique;	(rI31tBuindenyl)2(,1Cl)2Pd2 (id) (6.00 g, 9.58 mmol) and <strong>[244187-81-3]IPr</strong> (7.44 g, 19.16 mmol) were added to a 500 mL Schlenk flask. Diethyl ether (200 mL) was added to the flask via cannula. The resulting solution was stirred for 120 minutes. The solution was passed through a pad of silica gel, followed by the removal of solvent using a rotary evaporator to give 4d-<strong>[244187-81-3]IPr</strong> as an orange powder. Yield: 12.1 g, 91%.

Reference： [1]Patent: WO2016/57600,2016,A1 .Location in patent: Page/Page column 47; 48

62
[ 244187-81-3 ]
[ 1445-79-0 ]
(1,3-di-diisopropylphenylimidazol-2-ylidene)Ga(methyl)3 [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	In toluene; at -35 - 20℃;Glovebox; Inert atmosphere;	4.5 (<strong>[244187-81-3]IDipp</strong>)GaMe3 (4) In a N2-filled glovebox, a precooled (-35 C) toluene solution (10 mL) of GaMe3 (29.6 mg, 0.26 mmol) was added dropwise via a pipette to a precooled toluene solution (-35 C, 10 mL) of free carbene 1,3-di-diisopropylphenylimidazolin-2-ylidene (100.0 mg, 0.26 mmol) under stirring. The solution was stirred at room temperature overnight and then evaporated to dryness to give a colorless solid. The latter solid was washed twice with pentane (10 mL) to yield complex 4 in a pure form (128 mg, 99% yield). Anal. Calcd for C30H45GaN2 (503.41): C 71.58; H 9.01; found: C, 71.27; H 9.19. H NMR (300 MHz, CD2Cl2): δ = -1.33 (s, 9H, GaMe3), 1.21 (d, 12H, 3J = 6.9 Hz, CH3-iPr), 1.23 (d, 12H, 3J = 6.9 Hz, CH3-iPr), 2.66 (m, 4H, 3J = 6.9 Hz, CH-iPr), 7.13 (s, 2H, NCHCHN), 7.32 (d, 4H, 3J = 8.1 Hz, CH-Ar), 7.49 (t, 2H, 3J = 8.1 Hz, CH-Ar). 13C{1H} NMR (75 MHz, CD2Cl2): δ = -6,3 (GaMe3), 22.8 (CH3-iPr), 25.9 (CH3-iPr), 29.0 (CH-iPr), 124.1 (NCHCHN), 125.9 (CH-Ar), 130.5 (CH-Ar), 135.7 (C-Ar), 146.3 (Cipso-N), 182.9 (Ccarbene).

Reference： [1]Journal of Organometallic Chemistry,2016,vol. 820,p. 8 - 13

63
[ 50-00-0 ]
[ 74663-75-5 ]
[ 244187-81-3 ]

Yield	Reaction Conditions	Operation in experiment
		2,6-Diisopropylaniline (15 g, 84.7 mmol) was dissolved in 67 ml of 1-propanol and 15 in of water, after which glyoxal (40% aqueous solution, 5.6 g, 38.5 mmol) was added thereto. The reaction was carried out at 70 C. for 1 hour, the temperature was lowered to room temperature, and then the reaction product was filtered. The remaining solid was dissolved in methylene chloride, added with anhydrous magnesium sulfate and then filtered, after which the filtered solution was decompressed to a vacuum thus removing the solvent. The compound (5.048 g, 12.73 mmol) thus obtained and para-formaldehyde (0.458 g, 15.27 mmol) were dissolved in 83 ml of toluene and stirred at 100 C. for 2 hours. Thereafter, the temperature was lowered to 40 C., and hydrochloric acid (4 N, d=1.05 g/ml dioxane solution, 4.01 g, 15.27 mmol) was added thereto and thus the resulting precipitate was filtered. The solid compound thus obtained was dissolved in methylene chloride and dried over anhydrous magnesium sulfate, and the filtered solution was decompressed to a vacuum, thus removing the solvent. The compound (1.753 g, 4.124 mmol) thus obtained and potassium tert-butoxide (0.508 g, 4.537 mmol) were dissolved in 24 ml of THF and allowed to react with stirring for 4 hours. The solvent was removed using vacuum decompression, after which the product was dissolved in toluene and filtered using celite. The filtered solution was decompressed to a vacuum thus removing the solvent. The compound (1.335 g, 3.435 mmol) thus obtained and palladium allyl chloride (0.629 g, 3.435 mmol) were dissolved in 8 in of THF and stirred for 4 hours. The reaction solution was passed through silica gel and filtered, after which the solution was decompressed to a vacuum thus removing the solvent, giving the title compound of Formula 10 in which R1═R4=2,6-diisopropylphenyl; R2═R3═H; X1=allyl; X2═Cl.

Reference： [1]Patent: JP5662491,2015,B2 .Location in patent: Paragraph 0120-0122

64
[ 244187-81-3 ]
1,3-bis(2,6-diisopropylphenyl)imidazolium fluoride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hydrogenfluoride; In acetonitrile; for 16h;Inert atmosphere; Schlenk technique;	(LDipp) (n = 1.03 mmol; m = 400 mg) was weighed into 100 mL Schlenk flask and dissolved in 40 mL of THF or 20 mL MeCN. Solution was then cooled to 193 K, to which Et3N*3HF (n = 0.34 mmol (1 eq. of HF); m = 55.31 mg; ς = 0.989 mg mL-1; V = 55.9 mL) was added dropwise via syringe and left to warm up to R.T. and stirred for 16 h. Solvent was then slowly removed under vacuum. Solid residue was washed with toluene to afford single crystals of [(LDipp)H]+[F]- (1) in quantitative yields. Yield 370 mg (88 %). Melting point [C] = 130 (decomposition) 1H NMR (303 MHz, CD3CN, 25 C): δ 7.53-7.37 (m, 7H, ArH), 2.59 (singlet (broad), 4H, CH), 1.22 (d, J = 6.8 Hz, 12H, (CH3)2), 1.16 (d, J = 6.9 Hz, 12H, (CH3)2) ppm. 19F NMR (285.05 MHz, CD3CN, 25 C): δ -147.94 (s, 1F, F) ppm. Free fluoride determination: 4.4% (experimental), 4.6% (theoretical) Alternative synthesis of (1): (LDipp) (n = 2.57 mmol; m = 1000 mg) was weighed into 100 mL Schlenk flask and dissolved in 35 mL of MeCN. KHF2 (n = 2.56 mmol; m = 200 mg) was added and stirred for 16 h. Reaction mixture was then filtered through 0.45 mm syringe PTFE fliter, and the filtrate was left to slowly evaporate at room temperature, to afford single crystals of [(LDipp)H]+[F]- (1).

Reference： [1]Journal of Fluorine Chemistry,2016,vol. 192,p. 141 - 146
[2]Inorganic Chemistry,2017,vol. 56,p. 10070 - 10077

65
[ 244187-81-3 ]
F₂H^(1-)*C₂₇H₃₇N₂⁽¹⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With triethylamine tris(hydrogen fluoride); In tetrahydrofuran; at -80.16 - 20℃;Inert atmosphere; Schlenk technique;	(LDipp) (n = 0.51 mmol; m = 200 mg) was weighed into 100 mL Schlenk flask and dissolved in 20 mL of THF. Solution was then cooled to 193 K, to which a THF solution of Et3N*3HF (n = 0.34 mmol (2 eq. of HF); m = 55.31 mg; r = 0.989 mg mL-1; V = 55.9 mL) was added dropwise via syringe and left to warm up to room temperature and stirred for an additional hour. Solvent was then removed under vacuum. Compound (2) was then crystalized with slow evaporation of chloroform. Yield 201 mg (91 %) Melting point [C] = 223.4 - 227.1 (decomposition) 1H NMR (303 MHz, CD3CN, 25 C): δ 16.44-15.68 (t, 1H,1JHF = 115 Hz, [(HF)F]-), 10.01 (s, 1H, C(2)H), 7.83 (s, 2H, CHCH), 7.66-7.60 (m, 2H, ArH), 7.47-7.44 (m, 4H, ArH), 2.43 (hept, J = 6.5 Hz, 4H, CH), 1.26 (d, J = 6.9 Hz, 12H, (CH3)2), 1.19 (d, J = 6.9 Hz, 12H, (CH3)2) ppm. 19F NMR (285.05 MHz, CD3CN, 25 C): δ -147.50 (d, 2F, 1JHF =114 Hz, [(HF)F]-) ppm. Free fluoride determination: 8.6% (experimental), 8.8% (theoretical).

Reference： [1]Journal of Fluorine Chemistry,2016,vol. 192,p. 141 - 146

66
[ 244187-81-3 ]
F₃H₂^(1-)*C₂₇H₃₇N₂⁽¹⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With hydrogen fluoride; at 20℃;Cooling with liquid nitrogen; Inert atmosphere;	(LDipp) (n = 6.43 mmol; m = 2500 mg) was weighed to FEP vessel and frozen in liquid nitrogen. Approximately 10 mL of aHF was condensed over the frozen (LDipp) and left to warm to room temperature. Clear red-brown solution was evaporated on the vacuum line after 30 min. Single crystals of (3) were obtained from crystallization in FEP crystallization vessel where a small temperature gradient (10 K) was used for evaporation of aHF from the crystallization part. Yield 2300 mg (80 %) Melting point [C] = 232.1-235.1 (decomposition) 1H NMR (303 MHz, CD3CN, 25 C): δ 13.36 (s (broad), 2H, [(HF)2F]-) , 9.10 (t, J = 1.5 Hz, 1H, C(2)H), 7.90 (d, J = 1.5 Hz, 2H, CHCH), 7.69-7.64 (m, 2H, ArH), 7.50-7.47 (m, 4H, ArH), 2.43 (hept, J = 6.7 Hz, 4H, CH), 1.28 (d, J = 6.7 Hz, 12H, (CH3)2), 1.20 (d, J = 6.9 Hz, 12H, (CH3)2) ppm. 19F NMR (285.05 MHz, CD3CN, 25 C): δ -167.28 (s, 2F, [(HF)2F]-) ppm. Free fluoride determination: 13.3 % (experimental), 12.7 %(theoretical). Alternative synthesis of (3): (LDipp) (n = 0.51 mmol; m = 200 mg) was weighed into 100 mL Schlenk flask and dissolved in 20 mL of THF. Solution was then cooled to 193 K, to which a THF solution of Et3N*3HF (n = 1.02 mmol (6 eq. of HF); m = 164.4 mg; r = 0.989 mg mL-1; V = 167 mL) was added dropwise via syringe and left to warm to room temperature and stirred for an additional hour. Solvent and excess reagent wast hen removed under vacuum which afforded spectroscopically pure product (3).

Reference： [1]Journal of Fluorine Chemistry,2016,vol. 192,p. 141 - 146

67
manganese(ll) chloride [ No CAS ]
[ 244187-81-3 ]
[Mn₂Cl₂(μ-Cl)₂(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)₂] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	In tetrahydrofuran; at 20℃;Inert atmosphere;	The reaction of MnCl2 (0.30g, 2.4mmol) with IiPr (0.43g, 2.4mmol) was performed in THF (30mL) at room temperature overnight. The resulting yellow solution was evaporated to dryness, and the residue was washed with hexane (15mL×3). After extraction of the residue with THF (10mL), the extract was filtered with a syringe filter (0.2μm) to remove a small amount of insoluble solid and evaporated under reduced pressure. The residue was washed with hexane (10mL×2) and dried under vacuum to give 1a as a white solid (0.68g, 1.1mmol, 93%).

Reference： [1]Journal of Organometallic Chemistry,2016,vol. 820,p. 14 - 19

68
[ 244187-81-3 ]
C₂₇H₃₅N₆O₂^(1-)*Li⁽¹⁺⁾ [ No CAS ]

Reference： [1]Chemical Communications,2017,vol. 53,p. 4331 - 4334

69
[ 12427-42-8 ]
[ 244187-81-3 ]
C₃₇H₄₅CoN₂⁽¹⁺⁾*F₆P^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%		In a glovebox keeping the nitrogen atmosphere, a solution of 1,3-bis- (2,6- Diisopropylphenyl) imidazolylidene (IPr (1a), 0.12 g, 0.31 mmol, 1.00 equiv) The temperature was lowered to -20 while stirring for the liver. To the solution was added ferrocenium hexafluorophosphate (0.5 g, 1.00 Equiv), the solution was heated to 23 and reacted for 1.5 hours. Then, to purify the reactants Potassium tert-butoxide (0.13 g, 1.00 equiv) was added thereto and reacted for 0.5 hour. After termination of reaction The solids were removed in vacuo and the resulting solid was washed with toluene and filtered (5 x 5 mL). Then vacuum dried to brown A solid was obtained, taken out from the glovebox, washed with water (5 x 5 mL), and then transferred back to the glove box. The residue was dissolved in a small amount of dichloromethane (CH2Cl2), layered with ether (Et2O), and recrystallized at -20 to obtain the target compound (2a) (386.2 mg, yield = 71%).

Reference： [1]Patent: KR2017/51260,2017,A .Location in patent: Paragraph 0109-0111; 0120

70
ferrocenium hexafluorophosphate [ No CAS ]
[ 244187-81-3 ]
C₃₇H₄₅FeN₂⁽¹⁺⁾*F₆P^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%		In a glovebox keeping the nitrogen atmosphere, a solution of 1,3-bis- (2,6- Diisopropylphenyl) imidazolylidene (<strong>[244187-81-3]IPr</strong> (1a), 0.12 g, 0.31 mmol, 1.00 equiv) The temperature was lowered to -20 while stirring for the liver. To the solution was added ferrocenium hexafluorophosphate (0.5 g, 1.00 Equiv), the solution was heated to 23 and reacted for 1.5 hours. Then, to purify the reactants Potassium tert-butoxide (0.13 g, 1.00 equiv) was added thereto and reacted for 0.5 hour. After termination of reaction The solids were removed in vacuo and the resulting solid was washed with toluene and filtered (5 x 5 mL). Then vacuum dried to brown A solid was obtained, taken out from the glovebox, washed with water (5 x 5 mL), and then transferred back to the glove box. The residue was dissolved in a small amount of dichloromethane (CH2Cl2), layered with ether (Et2O), and recrystallized at -20 to obtain the target compound (2a) (386.2 mg, yield = 71%).

Reference： [1]Patent: KR2017/51260,2017,A .Location in patent: Paragraph 0109-0111

71
[ 1295-35-8 ]
[ 106-38-7 ]
[ 244187-81-3 ]
[ 613-33-2 ]
2C₃₄H₄₃N₂⁽¹⁺⁾*Br₄Ni^(2-) [ No CAS ]

Reference： [1]Dalton Transactions,2017,vol. 46,p. 12027 - 12031

72
cobalt pivalate [ No CAS ]
[ 244187-81-3 ]
C₃₇H₅₄CoN₂O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40%	In toluene; at 25℃; for 12h;Schlenk technique; Inert atmosphere;	[Synthesis Example 5] Synthesis of Cobalt Complex A (0209) A 20 mL Schlenk flask was charged with 0.20 g (0.77 mmol) of cobalt pivalate in Synthesis Example 3, 0.60 g (1.53 mmol) of 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene (abbreviated as <strong>[244187-81-3]IPr</strong>, hereinafter) and 20 mL of toluene, which were stirred at 25 C. for 12 hours. Then the solvent was distilled off in vacuum, followed by extraction with a diethyl ether/hexane mixture (10 mL/10 mL). The solution was vacuum concentrated to about 5 mL and recrystallized at -30 C., obtaining a clear crystal (0.20 g, yield 40%). The result of x-ray crystallography analysis on cobalt complex A is depicted in FIG. 1 and 1H-NMR spectrum is shown in FIG. 2. (0210) FT-IR (KBr) ν: 3158, 3123, 3077, 2962, 2924, 2871, 1586, 1565 [ν(COCtBu3-κ2)], 1549, 1530, 1482, 1463, 1447, 1413, 1358, 1331, 1258, 1222, 1181, 1117, 1100, 1061, 1028, 947, 938, 900, 807, 793, 752, 695, 610, 546, 536 cm-1 (0211) 1H-NMR (600 MHz, CDCl3) δ: -15.59 (s, 12H), 2.54 (br, 4H), 3.78 (s, 12H), 6.16 (br, 4H), 6.55 (br, 2H), 15.64 (s, 18H), 53.88 (s, 2H)

Reference： [1]Patent: US2017/260215,2017,A1 .Location in patent: Paragraph 0209; 0210; 0211

73
iron(II) pivalate [ No CAS ]
[ 244187-81-3 ]
C₃₇H₅₄FeN₂O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
26%	In toluene; at 25℃; for 12h;Schlenk technique; Inert atmosphere;	[Synthesis Example 6] Synthesis of Iron Complex B (0212) A 20 mL Schlenk flask was charged with 0.10 g (0.39 mmol) of iron pivalate in Synthesis Example 1, 0.18 g (0.46 mmol) of <strong>[244187-81-3]IPr</strong>, and 10 mL of toluene, which were stirred at 25 C. for 12 hours. Then hexane was added, followed by extraction. The solution was vacuum concentrated to about 5 mL and recrystallized at -30 C., obtaining a clear crystal (0.06 g, yield 26%). The result of x-ray crystallography analysis on iron complex B is depicted in FIG. 3 and 1H-NMR spectrum is shown in FIG. 4. (0213) 1H-NMR (600 MHz, CDCl3) δ: -38.68 (br, 4H), -7.07 (br, 12H), -4.05 (s, 12H), 22.99 (s, 4H), 24.32 (s, 2H), 26.18 (s, 2H), 33.68 (s, 18H)

Reference： [1]Patent: US2017/260215,2017,A1 .Location in patent: Paragraph 0212; 0213

74
[ 40935-25-9 ]
[ 244187-81-3 ]
[RuHCl(CO)(1,3-bis-(2,6-diisopropylphenyl)imidazole)(PCy₃)] [ No CAS ]

Reference： [1]Organic Letters,2017,vol. 19,p. 5204 - 5207

75
[ 124-38-9 ]
[ 244187-81-3 ]
C₂₇H₃₆N₂*CO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	In tetrahydrofuran; at 20℃; for 5h;Inert atmosphere;	General procedure: To a solution of free carbene IMes (0.6 g, 2 mmol) in THF (20 mL) was bubbled with CO2 to give a white precipitate immediately. After the reaction was being stirred for 5 h at room temperature, the mixture was filtered. The obtained white solid was washed withTHF for 3 times, and dried in vacuum. Yield: 0.45 g, 65%.

Reference： [1]Journal of Organometallic Chemistry,2016,vol. 808,p. 104 - 108

76
[ 7721-01-9 ]
[ 244187-81-3 ]
C₂₇H₃₈Cl₅N₂Ta [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	In toluene; at -40 - 0℃;Inert atmosphere;	To a solution of <strong>[244187-81-3]IPr</strong> (0.78 g, 2 mmol) in cold toluene (20mL, -40C ) was added TaCl5 (0.72 g, 2 mmol). The reaction was kept stirring overnight at 0C to give a yellow solid, which was filtered, washed three times by toluene and dried under the reduced pressure. Recrystalliztion of the crude residue in CH2Cl2 (15 mL) gave yellow crystals. Yield: 1.12 g, 75%. Anal. calcd forC27H37Cl5N2Ta(%): C, 43.37; H, 4.99; N, 3.75. Found(%): C, 43.47; H, 4.99; N 3.76. 1H NMR (600 MHz, CD2Cl2): δ 1.12 (d, 12H, J = 6.7, CH3), 1.37 (d, 12H, J = 6.9,CH3), 2.76 (m, 4H, J = 13.6, 6.8, CHMe2), 7.21 (s, 2H, NCH=), 7.30 (d, 4H, J = 7.8,m-C6H3) 7.49 (t, 2H , J = 7.8, p-C6H3); 13C{1H} NMR (150MHz, CD2Cl2): δ 22.95,25.94 (s, CH3), 29.24 (s, CHMe2), 124.45 (s, NCH=), 126.08 (s, m-C6H3), 131.06 (s,p-C6H3), 136.99 (s, o-C6H3), 146.36 (s, ipso-C6H3), 190.57 (s, NCN)

Reference： [1]Journal of Organometallic Chemistry,2016,vol. 808,p. 104 - 108

77
di-μ-tosyloxy-bis(3,3-dimethylureido-m-tolyl-2C,O)dipalladium (II) [ No CAS ]
[ 244187-81-3 ]
(tosyloxy)(3,3-dimethylureido-m-tolyl-2C,O)(IPr)palladium (II) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	In tetrahydrofuran; at 20℃;Inert atmosphere;	General procedure: General Procedure B for Preparation of mono-ligated arylpalladacycle Precatalysts of Formula I (0140) [0037] A flask (e.g. 25 mL) equipped with a magnetic stir bar, a nitrogen pad, and a rubber septum is charged with a palladacycle dimmer of Formula II (e.g. 0.5 mmol) and a solvent, such as THF (e.g. 5 mL) under nitrogen atmosphere. A ligand (1.0 mmol) in a solution or neat is then added. The mixture is stirred at room temperature until the reaction is deemed complete (30 min to 20 h) by H-NMR or 31P-NMR analysis. When the product precipitates out from the mixture, hexane (10 mL) is added to the reaction mixture and stirred for 10 min. The mixture is filtered, rinsed with hexane, and dried to afford the desired mono- ligated palladacycle precatalyst. If product does not precipitate, the solvent is evaporated under reduced pressure. The resulting residue is tritrated with hexane, filtered, rinsed with hexane, and dried to afford the desired mono-ligated palladacycle precatalyst. (0141Example 6- (Tosyloxy)(3,3-dimethylureido-m-tolyl-2C,0)(<strong>[244187-81-3]IPr</strong>)palladium (II) (6) (0152) [0041] Following substantially General Procedure B, compound 6 below was obtained as a gray solid in 94% yield from palladacycle dimer 1 and <strong>[244187-81-3]IPr</strong> in. In a 25-mL flask was added palladacycle dimer I (0.445 g, 0.82 mmol), <strong>[244187-81-3]IPr</strong> (0.34 g, 0.875 mmol), and THF (5 mL). The mixture was stirred at ambient temperature under nitrogen overnight. Hexane (10 mL) was added and stirred for 10 min. The solid was collected by filtering, rinsing with hexane, and drying at reduced pressure. It gave 0.65 g (94% yield) of product as a gray solid.

Reference： [1]Patent: WO2018/106336,2018,A1 .Location in patent: Paragraph 0037; 0038; 0041

78
[ 12079-65-1 ]
[ 244187-81-3 ]
Mn(η⁵-C₅H₅)(CO)₂(1,3-bis(2,6-diisopropylphenyl)imidazole-2-ylidene) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56%	In tetrahydrofuran;Inert atmosphere; UV-irradiation;	The synthetic and electrochemical work was carried out under a nitrogen atmosphere, using either standard Schlenk or drybox procedures. Dichloromethane and THF were purified by passing them down alumina columns under argon. [NBu4][PF6] supplied by Tokyo Kasei was recrystallized from 95% ethanol and dried at 100C under vacuum. Ferrocenium hexafluorophosphate, [FcH][PF6], was prepared as reported earlier [20]. 1,3-Bis(2,6-diisopropylphenyl)imidazole-2-ylidene (IDipp) (Fig. 1 ) and 1,3-bis(2,6-diisopropylphenyl)-4,5-dihydroimidazole-2-ylidene (IDippH2) were obtained from Strem Chemicals and used as received. MnCp(CO)3 (Strem) was purified by vacuum sublimation. Elemental analyses were carried out by the Robertson Laboratories. The cymantrenyl carbene complexes MnCp(CO)2(IDipp) (1) (Fig. 1) and MnCp(CO)2(IDippH2) were prepared by a modification of the photochemical process reported previously for 1 by Zheng et al. [7] Thus, a mixture of 90mg (0.44mmol) <strong>[12079-65-1]cymantrene</strong> and 205mg (0.53mmol) IDipp in 50mL THF was irradiated with a low pressure (12W) UV lamp. The progress of the substitution reaction was followed by taking samples for CO-range IR measurements, the photolysis being terminated when the intensity of the 2020cm-1 band for <strong>[12079-65-1]cymantrene</strong> was only a few percent of its original value. After the solvent was removed, the remaining brown solid was passed through a silica gel column using 1:1 petroleum ether:dichloromethane as the eluent. The second yellow band was collected and evaporated, giving 105mg (56%) of a yellow powder that analyzed for MnCp(CO)2(IDiip), 1: C, 72.49 (calc. 72.31), H 7.38 (calc. 7.33), N 4.92 (calc. 4.96); 1H NMR (CDCl3): δ (ppm) 1.12 (d, 12H), 1.40 (d, 12H), 2.80 (m, 4H), 3.87 (s, 5H), 6.96 (s, 2H), 7.32 (d, 4H), 7.48 (t, 2H). IR (CH2Cl2) νCO 1840, 1912cm-1. When an identical photochemical reaction was carried out on a mixture of <strong>[12079-65-1]cymantrene</strong> and the saturated NHC ligand IDippH2, less than 10mg of the yellow solid assumed to be MnCp(CO)2(IDiipH2) was obtained. The carbonyl-region IR spectrum of this sample (1844 and 1916cm-1) compared well with that of 1. A reversible one-electron oxidation (E1/2=-0.25V) was observed for this sample, but further studies were not carried out.

Reference： [1]Polyhedron,2019,vol. 157,p. 442 - 448

79
[ 244187-81-3 ]
[:(2,6-Prⁱ₂C₆H₃)]₂CHCLi}] [ No CAS ]

Reference： [1]Organometallics,2019,vol. 38,p. 375 - 384

80
tetraphenyiphosphonium trans-bis(trifluoromethyl)dichloroaurate [ No CAS ]
[ 244187-81-3 ]
trans-chlorobis(trifluoromethyl)-1,3-bis(2,6-diisopropylphenyl)-1,3-dihydro-2H-imidazol-2-ylidenegold(III) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	In toluene; for 1.13333h;Inert atmosphere; Sealed tube; Sonication; Glovebox; Darkness;	In a nitrogen-filled glovebox, Si (3.8 g, 5.04 mmol, 1 equiv) was slurried in Toluene (30 mL) and a solution of lPr free carbene (1.96 g, 5.04 mmol, 1 equiv) in Toluene (70 mL) was added. The mixture was sealed and brought out of the glovebox, sonicated for 8 minutes, and then stirred for an additional 1 hour. The mixture was concentrated onto Silica, and purified by chromatography eluting with 50% dichloromethane in hexanes, affording a pale yellow solid which was washed with hexanes to remove the co-eluting color impurity. This afforded the desired product as a colorless solid (3.2 g, 84% yield). X-ray quality crystals were obtained by vapor diffusion of hexanes into a saturated THF solution. A three dimensional molecule model is illustrated inFIG. 8.

Reference： [1]Patent: WO2018/217637,2018,A1 .Location in patent: Paragraph 0054; 0063

81
tetraphenyiphosphonium trans-bis(trifluoromethyl)methyliodoaurate [ No CAS ]
[ 244187-81-3 ]
trans-methylbis(trifluoromethyl)-1,3-bis(2,6-diisopropylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene-gold(III) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	In toluene; for 0.466667h;Inert atmosphere; Sealed tube; Sonication; Glovebox; Darkness;	In a nitrogen-filled glovebox, S2 (245 milligrams (mg), 0.30 mmol, 1.05 equiv) was slurried in Toluene (5 mL) and a solution of lPr free carbene (113 mg, 0.29 mmol, 1.0 equiv) in Toluene (15 mL) was added. The mixture was sealed and brought out of the glovebox, sonicated for 8 minutes, and then stirred for an additional 20 minutes. The mixture was concentrated onto Silica, and purified by chromatography eluting with 5% diethyl ether in hexanes,affording the desired product as a colorless solid (179 mg, 81% yield). X-ray quality crystals were obtained by layering hexanes onto a solution of la in diethyl ether. A three dimensional molecule model is illustrated in FIG. 5.

Reference： [1]Patent: WO2018/217637,2018,A1 .Location in patent: Paragraph 0054; 0058

82
[ 244187-81-3 ]
[ 1870-71-9 ]
C₂₉H₄₀BClN₂S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	In toluene; at 0 - 20℃; for 0.5h;Inert atmosphere;	IMes (7b, 1.61 g, 5.28 mmol) in toluene (15 mL) was added to a solution of chloro dithioborolane(6, 730 mg, 5.28 mmol) in toluene (10 mL) at 0 C.A bright yellowish solid was precipitated. The reaction mixture was stirred for 30 min at room temperature. After filtration, washing with toluene (30 mL) and subsequent drying in vacuo, the product was obtained as a white solid (93% yield). If required,further purification can be performed by slow diusion of pentane into a solution of the crude productin CHCl3.1H NMR (600.1 MHz, CDCl3): δ (ppm) = 7.10 (s, 2 H, NCH), 7.01 (s, 4 H, Mes-CH), 2.77 (s, 4 H,CH2), 2.36 (s, 6 H, Mes-para-CH3), 2.21 (s, 12 H, Mes-ortho-CH3).13C{1H} NMR (150.9 MHz, CDCl3): δ (ppm) = 158.4 (m, NCN), 140.7 (s, Mes-ipso-C), 136.1 (s,Mes-para-C), 133.5 (s, Mes-ortho-C), 129.4 (s, Mes-meta-CH), 123.3 (s, NCH), 37.3 (s, CH2), 21.4 (s,Mes-para-CH3), 18.5 (s, Mes-ortho-CH3).11B{1H} NMR (128.5 MHz, CDCl3): (ppm) = δ 5.5 (s, 12= 80 Hz).Elemental Analysis: Calcd. for C23H28BClN2S2: C 62.38, H 6.37, N 6.33, S 14.48. Found: C 62.04,H 6.16, N 5.89, S 14.25.

Reference： [1]Molecules,2019,vol. 24

83
[ 7783-68-8 ]
[ 244187-81-3 ]
C₂₇H₃₆F₅N₂Nb [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88.9%	In toluene; at 20℃; for 14h;Glovebox; Schlenk technique; Inert atmosphere;	NbF5 (200mg; 1.06mmol) and LDipp (414mg; 1.06mmol) were weighted into a Schlenk flask. Reactants were dissolved with 25mL of toluene. Reaction mixture was stirred for 14h at ambient temperature. Insoluble content was filtered off. Solvent was removed under dynamic vacuum. Remaining solid was used for elemental analysis, NMR and Raman spectroscopy. Slow evaporation of the solvent under static vacuum yields single crystals suitable for X-ray analysis. Yield: 546mg (88.9%). Elemental analysis requires for C27H36N2F5Nb (Mw=576.50g/mol): C 56.25, H 6.29, N 4.86%; found: C 56.47, H 6.39, N 4.91%. 1H NMR (303.0MHz, 25C, C6D6): δ 7.24 (t, J=7.7Hz, 2H, p-ArH), 7.10 (d, J=7.8Hz, 4H, m-ArH), 6.43 (s, 2H, CH=CH), 2.73 (sept, J=6.8Hz, 4H, CHMe2), 1.36 (d, J=6.7Hz, 12H, CH3), 1.00 (d, J=6.8Hz, 12H, CH3) ppm; 19F NMR (285.1MHz, 25C, C6D6): δ 152.5 (s, w1/2=207.0Hz) ppm.

Reference： [1]Journal of Fluorine Chemistry,2019,vol. 227

84
[ 7783-71-3 ]
[ 244187-81-3 ]
C₂₇H₃₆F₅N₂Ta [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83.6%	In toluene; at 20℃; for 14h;Glovebox; Schlenk technique; Inert atmosphere;	General procedure: NbF5 (200mg; 1.06mmol) and LDipp (414mg; 1.06mmol) were weighted into a Schlenk flask. Reactants were dissolved with 25mL of toluene. Reaction mixture was stirred for 14h at ambient temperature. Insoluble content was filtered off. Solvent was removed under dynamic vacuum. Remaining solid was used for elemental analysis, NMR and Raman spectroscopy. Slow evaporation of the solvent under static vacuum yields single crystals suitable for X-ray analysis. Yield: 546mg (88.9%).

Reference： [1]Journal of Fluorine Chemistry,2019,vol. 227

85
C₅₂H₈₀Au₂Cl₂O₄Si₄ [ No CAS ]
[ 244187-81-3 ]
C₅₃H₇₆AuClN₂O₂Si₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56%	In dichloromethane; for 12h;Inert atmosphere; Sealed tube; Glovebox;	In a glovebox, SI 4 and DCM (12 mL, 0.10 M) in an oven dried 20 mL vial was added free <strong>[244187-81-3]IPr</strong> carbene(1,3-Bis(2,6-diisopropylphenyl)-1,3- dihydro-2H-imidazol-2-ylidene) (0.46 g, 1.2 mmol, 1.0 equiv) in one portion. The reaction mixture was then stirred for 12 h and was then taken out of the glovebox. The reaction mixture was then filtered through a pad of celite and concentrated under reduced pressure.The crude product was then purified by column chromatography (3:2 DCM/Hexanes), yielding the title compound as an amorphous colorless solid (0.70 g, 56% yield). 1H NMR (500 MHz, Methylene Chlorided2)d 7.75 (d, J = 1.7 Hz, 1H), 7.42 (d, J = 7.9 Hz, 2H), 7.41 (s, 2H), 7.30 (dd, J = 7.8, 1.5 Hz, 2H), 7.24 (d,J = 7.9 Hz, 1H), 7.20 (dd, J = 7.8, 1.5 Hz, 2H), 7.15 (d, J = 7.8 Hz, 1H), 7.09 (dd, J = 7.9, 1.5 Hz, 1H),7.02 (dd, J = 7.7, 1.7 Hz, 1H), 6.71 (s, 1H), 4.61 (s, 2H), 4.56 (s, 2H), 3.20 (hept, J = 7.1 Hz, 2H), 2.95(hept, J = 6.5 Hz, 2H), 1.44 (d, J = 6.6 Hz, 6H), 1.17 (d, J = 6.8 Hz, 6H), 1.04 (d, J = 6.9 Hz, 6H), 0.97 (s,9H), 0.88 (s, 9H), 0.69 (d, J = 6.7 Hz, 6H), 0.16 (s, 6H), 0.04 (s, 6H) ppm. 13C NMR (101 MHz, MethyleneChloride-d2) d 188.40, 158.90, 153.23, 151.99, 151.93, 147.92, 145.50, 139.53, 138.96, 134.53, 131.72,131.11, 130.87, 126.52, 125.13, 124.98, 124.69, 121.37, 120.41, 65.73, 65.51, 29.48, 29.06, 26.90,26.64, 26.36, 26.17, 18.90, 18.71, -5.04, -5.15 ppm. HRMS (ESI+) m/z calcd for C53H76O2N2AuClNaSi2[M+Na]+: 1083.4692, found: 1083.4716. IR (neat, cm-1) 2957, 2929, 2858, 1592, 1462, 1402, 1363, 1325,1255, 1200, 1092, 1006, 939, 837, 804, 777, 757, 706, 667.

Reference： [1]Chem,2020,vol. 6,p. 142 - 152

86
[ 75732-01-3 ]
[ 244187-81-3 ]
C₃₆H₄₇CuN₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	In toluene; at 20℃; for 16h;Inert atmosphere; Schlenk technique;	A solution of 1,3-bis-(2,6-di-iso-propylphenyl)imidazolin-2-ylidene (4.15 g, 10.7 mmol) in 30 mL of toluene was transferred toa solution of mesityl copper(I) (1.96 mg, 10.7 mmol) in 100mL oftoluene via cannula and the solution was stirred overnight at roomtemperature. The solvent was removed under reduced pressure toobtain the crude product, which was washed with n-hexane anddried in vacuo. Yield: 5.07 g (8.88 mmol, 83%) of a colorless solid.Elemental analysis for [C36H47CuN2] [571.32 g/mol]: Calc. (obs.) C75.68 (76.28), H 8.29 (8.44), N 4.90 (5.32). Although the presentresults are outside the range viewed as established for analyzedpurity, they are provided to illustrate the best values obtained todate. In addition, the 1H and the 13C{1H} NMR spectra as given inthe SI provide some evidence for the purity of the compound. 1HNMR (200 MHz, 25 C, C6D6): δH/ppm = 1.10 (d, 12 H, 3JHH = 7 Hz,CHCH3), 1.37 (d, 12 H, 3JHH = 7 Hz, CHCH3), 2.08 (s, 6 H, m-CH3), 2.29(s, 3 H, p-CH3), 2.63 (sept, 4 H, 3JHH = 7 Hz, CHCH3), 6.31 (s, 2 H,NCHCHN), 6.91 (s, 2 H, m-CH), 7.08-7.12 (m, 4 H, mDipp-CH),7.23-7.31 (m, 2 H, p-CH). 13C{1H} NMR (50 MHz, 25 C, C6D6): δC/ppm = 21.7 (p-CH3), 23.8 (CHCH3), 25.1 (CHCH3), 28.0 (m-CH3), 29.1(CHCH3), 122.1 (NCCN), 124.2 (mDipp-CH), 124.6 (pDipp-CH), 130.4 (m-CH), 132.9 (p-Cq), 135.6 (iDipp-Cq), 146.1 (oDipp-Cq), 147.2 (o-Cq),163.3 (i-Cq), 186.4 (NCN). HRMS-ASAP (m/z): [M + H]+ calc. forC36H48CuN2, 571.3108 found, 571.3101.

Reference： [1]Journal of Organometallic Chemistry,2020,vol. 919

87
1,3-bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazolium tetrafluoroborate [ No CAS ]
[ 244187-81-3 ]
[ 258278-28-3 ]
1,3-bis(2,6-diisopropylphenyl)-4,5-dihydroimidazole trafluoroborate [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2021,vol. 60,p. 27253 - 27257
Angew. Chem.,2021,vol. 133,p. 27459 - 27463

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
{[ item.p_purity ]}	{[ item.pr_size ]}	{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]}	{[ getRatePrice(item.pr_usd, 1,1) ]}	Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]}	{[ item.pr_usastock ]}	Inquiry -	{[ item.pr_chinastock ]}	Inquiry -

CAS No. :	244187-81-3	MDL No. :	MFCD07781991
Formula :	C₂₇H₃₆N₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	VYCIHDBIKGRENI-UHFFFAOYSA-N
M.W :	388.59	Pubchem ID :	11271730
Synonyms :

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313	UN#:	N/A
Hazard Statements:	H315-H319	Packing Group:	N/A
GHS Pictogram:

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 244187-81-3 ] {[proInfo.proName]}

Quality Control of [ 244187-81-3 ]

Related Doc. of [ 244187-81-3 ]

Product Details of [ 244187-81-3 ]

Safety of [ 244187-81-3 ]

Application In Synthesis of [ 244187-81-3 ]

[ 244187-81-3 ] Synthesis Path-Upstream 1~3

[ 244187-81-3 ] Synthesis Path-Downstream 1~87

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry