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CAS No. : | 173035-11-5 | MDL No. : | MFCD11973794 |
Formula : | C21H26N2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 306.44 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P264-P280-P337+P313-P305+P351+P338-P302+P352-P332+P313-P362 | UN#: | |
Hazard Statements: | H315-H319 | Packing Group: | |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 88% 2: 67% | In hexane at 23℃; for 0.25h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | In tetrahydrofuran at 25℃; for 0.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With potassium <i>tert</i>-butylate; potassium hydride In tetrahydrofuran at 20℃; for 4h; | |
With sodium hexamethyldisilazane In tetrahydrofuran at 20℃; Inert atmosphere; | ||
With potassium hexamethylsilazane In diethyl ether Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | In benzene at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | In hexane byproducts: CO; (Ar); a soln. of ligand added to a soln. of Ni complex, stirred at room temp. for 2 h; volatiles removed in vac., washed (cold pentane); elem. anal.; | |
In hexane byproducts: CO; hexane soln. of ligand was treated with Ni(CO)4; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | In tetrahydrofuran at -78 - 20℃; Inert atmosphere; | |
74% | In dichloromethane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | In dichloromethane for 0.75h; Inert atmosphere; | |
89% | In dichloromethane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | In dichloromethane at -78℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | Stage #1: 4-(4-methylphenyl)methylene-2,6-di-tert-butyl-2,5-cyclohexanedien-1-one; 1,3-bis(2,4,6-trimethylphenyl)imidazolidin-2-ylidene In tetrahydrofuran at 20℃; Stage #2: With tetrafluoroboric acid In tetrahydrofuran; diethyl ether |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | In toluene at 20℃; for 1h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | In toluene at 20℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium t-butanolate In tetrahydrofuran at 30℃; for 2h; Inert atmosphere; | 3.2. Oxygen-atom insertion of in situ generated NHC-Copper complex 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. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | In toluene at 50℃; for 0.5h; Inert atmosphere; | 14 Synthesis of (S-I Mes)(PCy3)CI2Ru (3-2-methylphenyl-5-methyl-inden-1 -ylidene) A 10 mL vial was charged with (PCy3)2CI2Ru(3-2-methylphenyl-5-methyl-inden-1-ylidene) (10.3804 g, 0.4 mmol) and 5-IMes (1.1 eq., 0.134 g, 0.44 mmol). Dry toluene (3 ml) was added under inert atmosphere. The mixture was vigorously stirred at 50°C for 30 minutes and dried under vacuum followed by addition of 10 ml isopropanol. After filtration and washing (two times 5isopropanol), an orange powder was obtained; 0.33 g (Yield: 84%). The product was characterized by NMR spectra 1H, 13C, and 31P.1H NMR (300 MHz, CDCI3, TMS): 6 8.47 (d, 1 H), 7.44 (dd, 1 H), 7.20-7.28 (m, 2 H), 7.04-7.11 (m, 3 H), 6.99 (d, 1 H), 6.93 (s, 1 H), 6.88 (d, 1 H), 6.81 (s, 1 H), 6.05 (s, 1 H), 3.70-4.07 (m,4 H), 2.74 (s, 3 H), 2.68 (s, 3 H), 2.38 (s, 3 H), 2.33 (s, 3 H), 2.14 (s, 3 H), 2.02 (s, 3 H), 1.87 (s,3H), 0.86-1.83 (m, 36 H).13C NMR (75 MHz, CDCI3): 6 294.06, 293.96, 217.16, 216.19, 143.91, 140.11, 139.79,139.52, 139.39, 138.77, 138.29, 136.94, 136.85, 136.27, 135.69, 134.04, 130.70, 130.01, 129.88,129.57, 128.94, 128.58, 128.14, 127.25, 127.13, 126.27, 125.30, 125.05, 52.68, 52.64, 52.29,52.26, 33.09, 32.87, 29.47, 29.24, 27.70, 27.57, 26.20, 21.18, 20.91, 20.32, 20.15, 19.36, 18.97,18.92, 18.44.31P NMR(121.49 MHz, CDCI3): 626.75. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | In tetrahydrofuran at 50℃; for 24h; | I.2 SIMes (0.070 g, 0.228 minol) in 5 mL THF was added to a solution of Complex (3) (0.100 g, 0.1 14 mmol) in 5 mL of THF and the mixture was heated at 50 °C for 24 h. All volatiles were removed in vacuum. The product was extracted with toluene (10 mL) and filtered through celite. The solution was concentrated to 2 mL and penlane (15 mL) was added to the red solution to precipitate the product. Complex (4) was collected as red solid on a frit and dried under vacuum (0.076 g, 73%). NMR (400 MHz, CfiD6): δ 7.52 (t, %m = 8 Hz, 6H, Vl%), 6.94 (m, 1 I I I, PPh3 + Mes-CH), 6.82 (s. I I I. cs-C/7), 6.51 (s, I I I. Mes-C/7), 4.43 (dt, 2JW = 16 Hz, 3JHH = Hz, I I I. OCO-C//,), 3.60 (m, I H. OCO-CH2), 3.39-3.16 (in. 811, OCO-C + SIMes-CH2), 2.99 (s, 611, OCO-CH3 + Mes-CH,), 2.83 (br s, 5Η, Mes-C + OCO-C//2), 2.64 (s, 6Η, OCO-CH3 + Mes-C/7,), 2.33 (s, Η, Mes-C_), 2.13 i s. 3Η, Mes-CHj), 1.92 (s, 3Η, OCO-4,5-C// , 1.83 (s, 3Η, OCO-4.5-C//,), 1.59 (s, 311, Mes-CHj), -27.43 (d, 2Jm = 27 Hz, 1 H, Ru-//). 3 ,Ρ{} NMR (161 MHz, C6D6); δ 36.5 (s, PPh,). ,3C{'H} NMR (101 MHz, C6D6); δ 141.2 (d, lJPC = 29 Hz, Cips0, PPh3), 139.7 (Qpso), 135.0 (d. %c = 1 1 Hz, o-C, PPh3), 128.9 (d, 4JPC = 2 Hz, p-C, PPh3), 128.6 (Cipso)s 127.5 (d, %c = 8 Hz, m-C, PPh3), 125.7 (Cipso), 124.5 (OCO-4,5-C1pso), 122.2 (OCO-4,5-C,pso), 72.9 (0C0-C1 I2), 71.0 (OCO- CH2), 58.4 (OCO-CH3), 57.8 (OCO-CH3), 51.5 (SlMes-CI L), 50.8 (SIMes-C)5 46.5 (OCO~CH2)5 45.9 (OCO-CH2)5 21 .4 (Mes-CBj), 21.2 (Mes-CH3), 21.0 (Mes-CHj), 20.9 (Mes-C), 19.6 (Mes- C), 18.3 (Mes-CH3), 10.3 (OCO-4,5-CH3), 9.8 (OCO-4,5-CH3). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: dihydridotris(triphenylphosphine)ruthenium; C11H14OS2 In benzene at 50℃; for 2h; Stage #2: 1,3-bis(2,4,6-trimethylphenyl)imidazolidin-2-ylidene In benzene at 50℃; | III.3 Synthesis of Compound (2) To a C6H6 (1 mL) solution of Ru(PPh3)3(H)2 (20 mg, 0.0 174 mmol) was added the thioacetal (27) (5mg, 0.0221 mmol). The mixture was heated at 50°C in an oil bath for 2 hr and the yellow solutionturned dark red as bubbles were evolved. SiMes (6 mg, 0.0195 mmol) was added to the solution and the mixture was heated at 50°C for another hour. Pentane was added to the solution to crash out the red product which was washed with pentane. Spectral data match that of compound (2) previously reported. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Ru(PPh3)3HC1 (0.100 g, 0.108 mmol), thioacetal 27 (0.030 g, 0.130 mmol) and were dissolved in THF (5 mL) and toluene (5 mL) under N2. The solution was cooled to -78C and n-BuLi (0.068 mL, 1.6 M in hexanes) was added dropwise. The reaction mixture was stirred at -78C for 2 h and then allowed towarm to room temperature. After stirring at room temperature for another 2 h SiMes (0.050 g, 0.162 mmol) was added to the reaction mixture. The solution was then heated to 60C for 3 h. The solvent was removed and the resulting brown solid was dissolved in toluene (10 mL) and filtered through a plug of celite. The filtrate was concentrated and hexanes (20 mL) was added to precipitate 2 which was collected by filtration and washed with hexanes (3 x 5 mL) to give a red solid. All spectral datamatched that of compound (2). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: C11H14OS2; C36H68P2Ru*ClH; 1,3-bis(2,4,6-trimethylphenyl)imidazolidin-2-ylidene In toluene at -78℃; for 2h; Stage #2: With n-butyllithium In tetrahydrofuran; toluene at -78 - 25℃; for 2h; | II.3b Synthesis of Compound (2) SIMes was stirred with Ru(PCy3)2(H2)HC1 in toluene for 2 h. The solution was cooled to -78°C and nBuLi was added dropwise. The mixture was stirred for 2 h and allowed to warm to room temperatureand stirred for 2 h more. Compound (2) was isolated in an identical fashion to the procedure described inII.3a. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | In hexane at 50℃; for 18h; Inert atmosphere; | 1.7 Complex (Ib)-SIMes Complex (Ib)-SIMes was prepared from complex (3b)-PCy3 as follows:170mg of complex (3b)-PCy3 and 107mg of SIMes were dissolved in 13 mL of anhydrous hexane and the solution was stirred at 50°C for 18 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, 120 mg of yellow solid was obtained. The yield was 68.0%. The reaction was completely conducted under inert gas protection. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | In hexane at 50℃; for 17h; Inert atmosphere; | 1.11 Complex (Ic)-SIMes Complex (Ic)-SIMes was prepared from complex (3c)-PCy3 as follows:200mg of complex (3c)-PCy3 and 135 mg of SIMes were dissolved in 15 mL of anhydrous hexane and the solution was stirred at 50°C 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, 150 mg of yellow solid was obtained. The yield was 71%. The reaction was completely conducted under inert gas protection. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | In tetrahydrofuran at 23℃; for 3h; Inert atmosphere; | 1.14 Complex (Ib)-SIMes Complex (Ib)-SIMes was prepared from complex (3b)-PPh3 as follows:25 mg of complex (3b)-PPh3 and 13 mg of SIMes were dissolved in 4 mL of anhydrous THF and the solution was stirred at 23°C for 3 hours. Afterwards the solution was removed under vacuum. Then 0.5mL hexane was added to precipitate the yellow solid. The obtained precipitate was filtrated and washed two times with 0.5 mL hexane. After drying, 10 mg of yellow solid was obtained. The yield was 52%. The reaction was completely conducted under inert gas protection. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82.7% | In hexane at 50℃; for 17h; Inert atmosphere; | 1.3 Complex (Ia)-SIMes Complex (Ia)-SIMes is prepared from complex (3a)-PCy3 as follows:2 grams of complex (3a)-PCy3 and 1.45 grams of SIMes were dissolved in 100 mL of anhydrous hexane and the solution was stirred at 50°C for 17 hours. Afterwards the solution was cooled to room temperature and the obtained precipitate was filtered and washed three times with 3 mL hexane. After drying, 1.72 grams of yellow solid was obtained. The yield was 82.7%. The reaction was completely conducted under inert gas protection. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | In hexane at 50℃; for 18h; Inert atmosphere; | 1.1.7 Complex (Ib)-SIMes was prepared from complex (3b)-PCy3 as follows: 170 mg of complex (3b)-PCy3 and 107 mg of SIMes were dissolved in 13 mL of anhydrous hexane and the solution was stirred at 50°C for 18 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, 120 mg of yellow solid was obtained. The yield was 68.0%. The reaction was completely conducted under inert gas protection. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | In hexane at 50℃; for 17h; Inert atmosphere; | 1.1.11 Complex (Ic)-SIMes was prepared from complex (3c)-PCy3 as follows: 200 mg of complex (3c)-PCy3 and 135 mg of SIMes were dissolved in 15 mL of anhydrous hexane and the solution was stirred at 50°C 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, 150 mg of yellow solid was obtained. The yield was 71 %. The reaction was completely conducted under inert gas protection. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | In tetrahydrofuran at 23℃; for 3h; Inert atmosphere; | 1.1.14 Complex (Ib)-SIMes was prepared from complex (3b)-PPh3 as follows: 25 mg of complex (3b)-PPh3 and 13 mg of SIMes were dissolved in 4 ml . of anhydrous THF and the solution was stirred at 23 °C for 3 hours. Afterwards the solution was removed under vacuum. Then 0.5mL hexane was added to precipitate the yellow solid. The obtained precipitate was filtrated and washed two times with 0.5 ml. hexane. After drying, 10 mg of yellow solid was obtained. The yield was 52%. The reaction was completely conducted under inert gas protection. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82.7% | In hexane at 50℃; for 17h; Inert atmosphere; | 1.1.3 Complex (Ia)-SIMes is prepared from complex (3a)-PCy3 as follows: 2 grams of complex (3a)-PCy3 and 1 .45 grams of SIMes were dissolved in 100 ml. of anhydrous hexane and the solution was stirred at 50°C for 17 hours. Afterwards the solution was cooled to room temperature and the obtained precipitate was filtered and washed three times with 3 ml . hexane. After drying, 1.72 grams of yellow solid was obtained. The yield was 82.7%. The reaction was completely conducted under inert gas protection. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | In tetrahydrofuran for 24h; Reflux; | Synthesis of cyclic bent allene metal complex 3 - Ru(CBA)(SIMes)(CO)HCl To a solution of 1 (150 mg, 0.130 mmol) in THF (5 mL) was added SIMes (140 mg, 0.457 mmol) and the solution was re-fluxed for 24 hours. The solution was cooled to room temperature and concentrated to approximately 1 mL. Pentane (15 mL) was added to precipitate the product as a bright yellow-orange solid, which was washed with pentane (3 x 10 mL) and dried under high vacuum (111 mg, 92%). (0167) 1H-NMR(C6D6): 6.88 (br s, 2H, Mes), 6.86-6.77 (m, 6H), 6.75 (d, 3JH-H = 8.0 Hz, 4H, m-OAr), 6.65 (br s, 2H, Mes), 6.60-6.57 (m, 6H), 3.30 (m, 4H, NCH2CH2N), 2.73 (br s, MesCH3, 6H), 2.51 (br s, MesCH3, 6H), 2.15 (br s, OArCH3, 12H), 2.05 (br s, MesCH3, 6H), -26.04 (s, 1 H, Ru-H). (0168) 13C-NMR (CD2Cl2): 221.40 (CO), 203.37 (NCN), 171.39 (NCO), 152.38, 137.71, 137.64, 137.11, 136.81, 134.91, 130.38, 129.33, 129.30, 129.18, 128.93, 128.76 (br), 127.71, 125.41, 114.12 (CC(Ru)C), 51.18 (NCCN), 20.96 (MesCH3), 19.20 (MesCH3), 19.15 (MesCH3), 16.76 (br, XylCH3). (0169) IR(KBr): 1881 cm-1 (vCO). (0170) Anal. Calcd. for C53H55ClN4O3Ru (932.55): C, 68.26; H, 5.94; N, 6.01. Found: C, 68.22; H, 5.38; N, 5.83. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | In benzene for 3h; Inert atmosphere; | |
81% | In benzene for 3h; Inert atmosphere; | 6 Example 6 Preparation of Mo(N-2,6-Me2-C6H3) (IMesH2)-(CHCMe2Ph) (OTf)2 (6) Example 6 Preparation of Mo(N-2,6-Me2-C6H3) (IMesH2)-(CHCMe2Ph) (OTf)2 (6) (0105) Mo (N-2, 6-Me2-C6H3) (CHCMe2Ph) (OTf) 2 (DME) (0.20 g, 0.2720 mmol) was initially charged in 8 mL of benzene: 1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidin-2-ylidene (0.0830 g, 0.2720 mmol) was dissolved in 1 mL of benzene and added dropwise. In the course of this, a rapid color change from a yellow to dark red was observed with simultaneous formation of a precipitate. (0106) After stirring for three hours, the benzene was then decanted off, and the residue was washed with benzene and dried under reduced pressure. The product was isolated as a yellow solid (0.15 g, 81%). Alternatively, the yellow solid can be dissolved in a minimal amount of dichloromethane and crystallized at -30° C. for 24 h, giving a crystalline yellow material with 69% yield. 1H NMR (CD2Cl2): δ=13.11 (s, 1H, CHCMe2Ph, JCH=114 Hz), 7.19-6.95 (m, 9H, ArH), 6.51 (s, 2H, ArH), 3.97 (s, 4H, CHNC), 2.69-1.71 (s, 27H, Me), 1.25 (s, 3H, CHCMe2Ph) ppm; 19F NMR (CD2Cl2): δ=-74.59 (s, CF3SO3, trans to the NHC ligand), -76.53 (s, CF3SO3); 13C NMR (CD2Cl2): δ=317.4 (CHCMe3), 208.7 (CNcarbene), 154.6 (Cipso), 149.0, 140.4 (Cortho), 137.0 (Caryl), 136.4 (Caryl), 135.6 (Caryl), 130.9 (Caryl), 130.5 (Caryl), 130.2 (Caryl), 128.4 (Caryl), 128.2 (Caryl), 126.9 (Caryl), 125.9 (Caryl), 121.6 (q, CF3, J=319 Hz), 118.5 (q, CF3, J=320 Hz), 56.8 (CMe2Ph), 53.1 (CH2 imidazolylidene), 32.9 (CMe2Ph), 29.6 (CMe2Ph), 21.3 (CH3), 19.0 (CH3), 18.9 (CH3); elemental analysis: C41H47F6MoN3O6S2; calculated: C, 51.68; H, 5.02; N, 4.41. found: C, 51.81; H, 4.88; N, 4.35. |
at -35 - 20℃; for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | In tetrahydrofuran at 20℃; Glovebox; Schlenk technique; Sealed tube; | |
87% | In benzene at 20℃; for 72h; | Synthesis of 2 Tetrafluoroethylene was bubbled through a solution of 0.10 g(0.33 mmol) of 1 in 20 mL of benzene for 3 h at room temperature over which time a light yellow color developed. Themixture was stirred for 3 days at room temperature. Evaporation of the solvent gave 2 as a light yellow, oily solid. Yellow needles were obtained by recrystallization fromhexane at -25°C. Yield:0.117 g (87%); mp. 186°C. 1H NMR (C6D6) δ = 2.09, 2.10 (s,6 H, p-CH3), 2.26, 2.27 (s, 12 H, o-CH3), 3.06 (s, 4 H, Im H4/5),6.73, 6.76 (s, 4 H, PhH3/5); 13CNMR(C6D6) δ =18.04, 18.19 (s,o-CH3), 20.88, 20.92 (s, p-CH3), 49.92, 51.62 (s, ImC4/5), 119.29(dq, J=197.2Hz, J=43.9Hz, CF), 124.20 (qd, J=264.3Hz, J=33.6 Hz, CF3), 129.58, 129.89 (s, Ph C2/6), 135.67 (q, J = 1.2 Hz,Ph C2/6), 135.90 (d, J = 3.0 Hz, Ph C2/6), 136.59, 136.79 (s, PhC4), 138.25 (d, J = 3.1 Hz, Ph C1), 139.20 (q, J = 1.2 Hz, Ph C1),144.59 (dq, J = 17.1 Hz, J = 1.8 Hz, Im C2); 19F NMR (C6D6)δ =-205.0 (q, J = 15.5 Hz, 1 F, CF), -60.4 (d, J = 15.5 Hz, 3F, CF3); MS (EI, 70 eV); m/z (%): 406 (30) (M+), 405 (40) (M+- H), 391 (55) (M+ - CH3), 305 (100) (M+ - C2HF4), 246 (15)(M+ - C9H11). Anal. Calcd for C23H26F4N2: C, 67.96; H, 6.45;N, 6.89. Found: C, 67.89; H, 6.63; N, 6.89. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | In hexane at 20℃; | Synthesis of 3 Hexafluorocyclobutene (0.411 g, 2.5 mmol) was condensed at-196°Cvia a vacuum line to a solution of 0.115 g (0.38mmol) of 1 in 30mLof hexane. The reaction was warmed to room temperature after which point the mixture became cloudy and 3 precipitated as a colorless solid. After stirring for 20 h at room temperature,the precipitate was filtered off and dried in vacuo. Yield: 0.144 g (81%); mp. 242°C (dec); 1H NMR (C6D6) δ = 2.07 (s,6 H, p-CH3), 2.20 (s, 12 H, o-CH3), 2.98 (s, 4 H, Im H4/5), 6.77(s, 4 H, Ph H3/5); 13C{1H} NMR (C6D6) δ = 17.59 (s, o-CH3),21.02 (s, p-CH3), 49.42 (s, ImC4/5), 69.4-70.0 (m, C2-C), 111.7-120.5 (m, CF2CF2CF2, CF2CF2CF2), 129.80 (s, Ph C3/5), 133.25(s, Ph-C1), 137.16 (s, Ph C2/6), 139.02 (s, Ph C4), 156.9-157.3(m, Im C2); 13C{19F} NMR (C6D6) δ = 17.59 (q, J = 130.03 Hz,o-CH3), 20.97 (q, J = 130.60 Hz, p-CH3), 49.39 (t, J = 145.26Hz, ImC4/5), 69.73 (s, (C2-C), 115.97 (s, CF2CF2CF2), 116.42 (s,CF2CF2CF2), 129.94 (d, J = 140.19 Hz, Ph C3/5), 132.8-133.8(m, Ph C1), 137.14 (q, J = 6.12 Hz, Ph C2/6), 139.03 (q, J =6.12 Hz, Ph C4), 157.09 (s, Im C2); 19F{1H} NMR (C6D6): δ =-128.3 (quint, 2 F, J=8.0Hz, CF2CF2CF2),-94.9 (t, 4 F, J=7.7Hz, CCF2CF2); MS (EI, 70 eV) m/z (%) 468 (65) (M+), 467 (75)(M+ - H), 449 (15) (M+ - F), 367 (10) (M+ - C2HF4), 148 (100)(C10H14N+). Anal. Calcd for C25H26F6N2: C, 64.09; H, 5.59; N,5.98. Found: C, 63.76; H, 5.82; N, 5.90. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | In hexane; toluene at 20℃; for 1h; | Synthesis of 4 To a solution of 0.102 g (0.33 mmol) of 1 in 30 mL of hexane,0.120 g (0.57 mmol) of octafluorocyclopentene in 5 mL of toluene were added at room temperature. The color of the mixture turned to yellow immediately. After stirring for 1 h at room temperature, the solvents were evaporated and 4 was obtained as a crystalline yellow solid. Yield: 0.161 g (94%); mp. 203 - 204°C(dec); 1H NMR (C6D6): δ = 2.07 (s, 6 H, p-CH3), 2.21 (s, 12H, o-CH3), 2.94 (s, 4 H, ImH4/5), 6.71 (s, 4 H, Ph H3/5); 13C{1H}NMR(C6D6) δ =17.76 (s, o-CH3), 20.92 (s, p-CH3), 50.76 (s, ImC4/5), 66.07 (m,C2-C), 111.0-121.7 (m,CF2), 129.86 (s, PhC3/5),135.78 (q, Ph C2/6), 136.77 (m, Ph C1), 138.13 (q, Ph C4), 160.41(s, Im C2); 13C{19F} NMR (C6D6) δ = 17.76 (qt, J = 126.97 Hz,J = 2.42 Hz, o-CH3), 20.92 (qt, J = 126.30 Hz, J = 4.31 Hz, p-CH3), 50.77 (t, J = 148.62 Hz, Im C4/5), 66.07 (s, C2-C), 111.51,118.18 (s, CF2), 129.85 (dm, J = 156.3 Hz, Ph C3/5), 135.78 (q, J= 5.5 Hz, Ph C2/6), 136.78 (m, Ph C1), 138.13 (q, J = 6.1 Hz, PhC4), 160.41 (s, Im C2); 19F NMR (C6D6): δ = -135.0 to -134.0(m, 4 F, CF2CF2CF2), -92.6 to -92.2 (m, 4 F, CCF2CF2); MS(EI, 70 eV) m/z (%) 518 (80) (M+), 517 (95) (M+ - H), 499 (55)(M+ - F), 305 (100) (M+ - C5F8), 148 (70) (C10H14N+). Anal.Calcd for C26H26F8N2: C, 60.23; H, 5.05; N, 5.40. Found: C,60.24; H, 5.34; N, 5.27.Synthesis of 7 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | In diethyl ether; at 20℃; for 0.333333h;Inert atmosphere; | Bis(1,5-cyclooctadiene)nickel(0) (0.50 g, 1.82 mmol) wasdissolved in diethyl ether (20 mL). A solution of SIMes (1.12 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 for 20 minutes the volatiles were removed under reduced pressure. The solid was dissolved in 10 mL of n-pentane and cooled at -35 C to give 1.12 g (92 %) of 1-SIMes as dark purple crystals. 1H NMR (298 K, 500.13 MHz, C6D6): 6.73 (s, 8H, C6H2), 3.80 (s, 8H, NC2H4N), 2.30 (s,12H, C6H2(CH3)3), 1.94 (s, 24H, C6H2(CH3)3); 13C{1H} NMR (20C, 125.76 MHz, C6D6): 203.7, 144.4, 136.4, 131.3, 129.8, 54.4, 22.9, 19.5. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | In tetrahydrofuran at 20℃; Glovebox; Schlenk technique; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | In tetrahydrofuran at 20℃; Glovebox; Schlenk technique; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | In tetrahydrofuran at 20℃; for 2h; | 1 Embodiment 1:Ni[P (OR1)3] [(R2NCH2CH2NR2) C]X2(R1= CH2CH3, R2= 2, 4, 6-trimethyl phenyl, X =Br) synthesis of The n-heterocyclic carbene (R2NCH2CH2NR2) C (0.2464g, 0.8 mmol) is added to the b (triethyl phosphite) nickel (II) dibromide (0.4400 g, 0.8 mmol) in the thf solution, the reaction at room temperature 2 hours, vacuum to remove the solvent, washing the residue with n-hexane, the resulting residue in toluene extraction, solvent transfer supernatant fluid and removing toluene, to obtain red solid, yield is 68%. |
68% | In tetrahydrofuran at 20℃; for 2h; | 1 Example 1: Synthesis of Ni[P(OR1)3][(R2NCH2CH2NR2)C]X2 (R1=CH2CH3, R2=2,4,6-trimethylphenyl, X=Br) Add a nitrogen heterocyclic carbene (R2NCH2CH2NR2) C (0.2464 g, 0.8 mmol) to the solution of di(triethyl phosphite) nickel dibromide (0.4400 g, 0.8 mmol) in tetrahydrofuran, react at room temperature for 2 hours, the solvent was removed in vacuum, the residue was washed with n-hexane, and the obtained residue is extracted by toluene, and the clear liquid is transferred, and solvent toluene is removed, so as to obtain a red solid, wherein the yield is 68%. The results of elemental analysis of the product are shown in Table 1: |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | In benzene for 3h; Inert atmosphere; | 1 Example 1 Preparation of Mo(N-2,6-Me2-C6H3) (IMesH2) (CH-tBu) (OTf)2) (1) Example 1 Preparation of Mo(N-2,6-Me2-C6H3) (IMesH2) (CH-tBu) (OTf)2) (1) (0100) Mo(N-2,6-Me2-C6H3) (CH-tBu) (OTf)2 (DME) (0.300 g, 0.445 mmol) were dissolved in 8 mL of benzene, and a solution of 1,3-bis(2,4,6-trimethylphenyl)-2-imidazolinylidene (0.136 g, 0.445 mmol) in 5 mL of benzene was added. The reaction solution was stirred for three hours, the benzene was decanted off, and the residue was washed with benzene. Yield: 0.32 g (81%, yellow powder). It was possible to obtain crystalline material by recrystallization from CH2Cl2. 1H NMR (CD2Cl2): δ (syn isomer, 99.9%) 12.76 (s, 1, CHCMe3, JCH=118 Hz), 7.06-6.61 (7H, ArH), 3.98 (4H, CH2NC), 2.69-1.71 (24H, Me), 0.93 (s, 9H, CH2CMe3); 19F NMR (CD2Cl2): δ-74.65 (SO3CF3), -76.7 (SO3CF3). 13C NMR (CD2Cl2): δ 320.9 (CH-tBu), 208.7 (CNcarbene), 154.6 (Cipso), 140.4 (Cortho), 137.1 (Caryl), 136.8 (Caryl), 135.7 (Caryl), 131.1 (CHaryl), 130.5 (CHaryl), 130.1 (CHaryl), 128.2 (Caryl), 120.2 (q, CF3, J=319 Hz), 119.8 (q, CF3, J=320 Hz), 53.1 (CMe3), 50.7 (CH2-imidazolylene), 30.5 (CMe3), 21.3 (CH3), 19.0 (CH3), 18.9 (CH3); anal. calc. for C36H45F6MoN3O6S2.CH2Cl2: C, 45.54; H, 4.96; N, 4.31. Found: C, 45.52; H, 4.75; N, 4.37. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | In toluene at -40 - 20℃; for 2h; Glovebox; Schlenk technique; Inert atmosphere; | 5 Example 5 (Preparation of Mo(N-2,6-Cl2-C6H3) (CHCMe3)-(OTf)2(IMesH2)) (5) Example 5 (Preparation of Mo(N-2,6-Cl2-C6H3) (CHCMe3)-(OTf)2(IMesH2)) (5) (0104) In a glovebox, Mo(N-2,6-Cl-C6H3) (CHCMe3) (OTf)2(DME) (0.198 g, 0.277 mmol) was initially charged in a 25 mL Schlenk flask. The complex was dissolved in 15 mL of toluene and cooled at -40° C. for 30 min. 1,3-Dimesitylimidazol-2-ylidene (0.085 g, 0.277 mmol, 1 equiv.) was dissolved in 3 mL of toluene and likewise cooled. While stirring, the cold NHC solution was added dropwise to the metal complex. The color changed gradually to dark orange. The reaction mixture was stirred at room temperature for 2 h. After a few minutes, cloudiness set in and a precipitate formed. Subsequently, the solvent was concentrated to about 1/3 and the suspension was frozen for 30 min. The precipitated solids were filtered off and washed with a little cold toluene. The crude product is obtained as a yellow solid and can be recrystallized from dichloromethane (0.185 g, 72%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | In toluene at 20 - 45℃; for 5h; Inert atmosphere; | 1 Example 1 10.6 g of catalyst RuCl2(sIMes)(CHPh)(Py)2 (C727) (14.6 mmol) were placed in a round-bottomed flask, to which 6.7 g of sIMes (21.9 mmol) and 50 mL of anhydrous toluene were added under nitrogen. The round-bottomed flask was placed in a warm water bath at 45°C and after 1 h, the bath was allowed to cool at room temperature. The reaction mixture was stirred for 3 additional hours and the reaction progression was followed by NMR. Since the reaction was incomplete, additional sIMes (2.0 g, 6.5 mmol) was added. The solution was stirred at room temperature for another hour. The solvent was removed under high vacuum and MeOH (degassed, 150 mL) was added to the mixture. After stirring for 10 minutes, the reaction mixture was filtered and the solid was washed with MeOH until the filtrate became colorless. The crude compound was dissolved in CH2C12, filtered on a silica gel plug, and recrystallized from CH2Cl2/MeOH. C875bis was obtained in 80% yield as a light brown solid. Purity: 99+% by HPLC. The NMR matched the published data. |
63% | In benzene for 24h; Inert atmosphere; Glovebox; | |
63% | In benzene at 45℃; for 24h; Inert atmosphere; Glovebox; | 2.B.ii (ii) Synthesis of RuCl2(CHPh)(SIMes)2 RuCl2(CHPh)(SIMes)2 was prepared as described in Trnka, J. Am. Chem. Soc., 2003, 125, 2546-2558. In a glovebox, a 25 mL round bottom flask was charged with RuCl2(CHPh)(Py)2(SIMes) (196 mg, 270 μmol), SIMes (83 mg, 270 mmol) and benzene (9 mL). The brown reaction mixture was stirred at 45° C. for 24 h before being cooled to room temperature and concentrated under vacuum. The crude residue was then precipitated from cold pentane (-20° C.), filtered and washed with cold pentane (-20° C.). To improve its purity, the complex was extracted multiple times with boiling hexanes. The precipitate was therefore taken up in boiling hexanes and filtrated through a collection frit. This was repeated multiple times to recover most of the desired complex. The combined organic layers were finally concentrated under vacuum to furnish the desired RuCl2(CHPh)(SIMes)2 as a brown solid (150 mg, 171 μmol, 63% yield). The NMR data are in agreement with the literature values. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | In toluene for 2h; Inert atmosphere; | 2 6.2 g of catalyst RuCl2(sIMes)(CHCH=C(CH3)2)(Py)2 (C705) (8.8 mmol) were placed in a round bottomed flask together with 4.0 g of sIMes (13.2 mmol) and 100 mL of anhydrous toluene, under nitrogen. After stirring the reaction mixture for 2 hours, the solvent was removed under vacuum. The residue was dissolved in degassed CH2CI2 (25 mL), filtered on a silica gel plug. The filtrate was concentrated and dissolved in 100 mL of degassed MeOH, the mixture was further concentrated under vacuum until a significant amount of crystalline material crashed out of the solution. The crystals were filtered and washed with MeOH, dried under high vacuum and recrystallized from CLhCh/MeOH. C853Bis was obtained in 65% yield as an olive crystalline solid. Purity: 98+% by HPLC. MR (CD2CI2): δ 18.50 (d, J = 10 Hz, Ru=CH, 1 H), 6.94 (d, J = 11 Hz), 6.71 (b, 8 H), 3.49 (b, 8 H), 2.7 - 1.9 (b, 36 H), 0.78 (s, 3 H), 0.48 (s, 3 H). 13C MR (CD2C12): δ 289.39 (m, Ru=CH), 221.22, 145.87, 145.84, 138.16, 136.94, 139.0 - 136.5 (b), 130.43, 131.0 - 129.0 (b), 129.26, 52.92, (b), 27.72, 21.47, 20.26, 19.06. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | In toluene at 20 - 50℃; for 19h; Inert atmosphere; | 3 Example 3 RuCl2(sIMes)2(Ph-Indenylidene) (C975Bis) 10.1 g of catalyst [RuCk(sIMes)(Phenyl-Indenylidene)(Py)] FontWeight="Bold" FontSize="10" (Py)2.o (C748 · (Py)2.o) (16.7 mmol) were placed in a round bottomed flask under N2, together with 5.1 g of sIMes (16.7 mmol) and 40 mL of anhydrous toluene, under nitrogen. The reaction mixture was stirred for 3 hours, in a water bath at 30-50°C and for 16 additional hours at RT. The solvent was removed under vacuum. The residue was dissolved in degassed MeOH (80 mL), filtered and the solid was washed with MeOH. The solid was dried under high vacuum, then dissolved in CH2Cl2/EtOAc and filtered on a silica gel plug. The filtrate was diluted with MeOH and the crystalline solid obtained was dried under vacuum. C975bis was obtained as a dark purple crystalline material in 80% yield. The MR matched the published data. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | In toluene; at 20 - 45℃; for 19h;Inert atmosphere; | 2.0 g of catalyst RuCl2(sIMes)(CH-o-CPrO)C6H4) (C627) (3.2 mmol) and 1.46 g of sIMes (4.8 mmol) were placed in a round bottomed flask under nitrogen, in 10 ml of anhydrous toluene. The reaction mixture was heated in a water bath at 45 C and stirred for 3 h and another 16 h at room temperature. The formed suspension was filtered and washed with MeOH. C933Bis was obtained as a light pink solid in 40% yield. Purity: 99+% by HPLC. NMR (CD2CI2): delta 20.04 (s, 1 H), 8.46 (d, J = 10 Hz, 1 H), 7.17 (t, J = 8 Hz, 1 H), 7.1 - 6.3 (b, 6 H), 6.40 (t, J = 7 Hz, 1 H), 6.21 (d, J = 8 Hz, 1 H), 6.1 - 5.7 (b, 2 H), 4.07 (septet, J = 6 Hz, 1 H), 3.7 - 3.3 (b, 8 H), 2.7 - 1.7 (b, 36 H), 1.48 (d, J = 6 Hz, 6 H). 13C NMR (CD2CI2): delta 289.16 (m, Ru=CH), 220.80, 148.12, 142.58, 139.0 - 135.0 (b, m), 134.43, 130.15 (b), 129.33, 119.53, 119.78, 70.08, 55.0 - 52.0 (b), 23.40, 21.46, 19.47, 20.0 - 18.0 (b). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | In tetrahydrofuran at 25℃; for 2h; Inert atmosphere; Glovebox; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With potassium graphite In benzene at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With La(O-C6H3-2,6-(t-Bu)2)3; hydrogen In benzene-d6 at 20℃; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | In toluene at 20℃; Inert atmosphere; Glovebox; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | In toluene at 20℃; Inert atmosphere; Glovebox; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
36% | In benzene at 20℃; Inert atmosphere; Glovebox; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | In dichloromethane at 20℃; for 1h; |
Tags: 173035-11-5 synthesis path| 173035-11-5 SDS| 173035-11-5 COA| 173035-11-5 purity| 173035-11-5 application| 173035-11-5 NMR| 173035-11-5 COA| 173035-11-5 structure
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H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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