Benzylidene-bis(tricyclohexylphosphine...
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Benzylidene-bis(tricyclohexylphosphine...
structure -
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CAS No:
172222-30-9
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Formula:
C43H72Cl2P2Ru
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Chemical Name:
Benzylidene-bis(tricyclohexylphosphine...
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CAS No:
Characteristics
27.18000
10.59820
Purple Solid
153 °C (dec.)(lit.)
383.4°C at 760 mmHg
195.6ºC
2-8°C
9.7E-06mmHg at 25°C
Safety Information
Ⅱ
4.1
1325
3
36/37/38-11
26-36
Xi,F
P210-P261-P305 + P351 + P338
H228-H315-H319-H335
Benzylidene-bis(tricyclohexylphosphine... Use and Manufacturing
Potassium bis(trimethylsilyl)amide (1 .4 g, 7.0 mmol, 1.23 equiv) was added to a suspension of dihydroimidazolium salt 4 (compound 4 of reaction scheme 3) (2.3 g, 6.7 mmol, 1.15 equiv) in toluene (57 mL) under argon. The reaction mixture was stirred at r.t. for 30 min, then compound 5 (4.7 g, 5.7 mmol) was added and stirring was continued for 1.5 h at r.t. The reaction mixture was then concentrated and catalyst 6 was isolated by column chromatography and dried in vacuo.SnCl4 (36ml 25mL, 0.2 mol) and 1, 2- dichloroethane(240ml 200ml) were added into a 1 L three-necked flask with drop funnel, stirrer bar and temperature indicator under Ar atmosphere and cooled to -50°C by dry ice acetone bath. Keep temperature at -50°C, tributylamine (72ml 50ml, 0.2mol) was added and stirred for 1 hr. Followed by inletting acetylene at -50°C for 6 hr, 2-chorophenol (6.50g, 50mmol) was added at room temperature. After finishing the addition, the mixture was heated at 70°C for 2 hrs, and ortho-vinylphenol was obtained. After the reaction was completed, K2CO3 (25g) and methanol (100ml) were added and heated to 60°C for 1 hr, dropped HCl (2N) with ice baths to adjust pH value lower than 2. Extracted with ethyl acetate (2 .x. 300ml), dried over Na2SO4, then the majority of ethyl acetate was removed by rotovap, extracted with the mixed solution of ethyl acetate and petroleum ether(1:1, 2 .x. 300ml), dried over Na2SO4, the mixed solvent was removed by rotovap, 4.83g of ortho-vinylphenol was obtained by silica gel column chromatography(yield: 63percent, purity: 98percent). It is certified that the product is ligand of Ru complex. 1H NMR (400 MHz, CDCl3: delta= 7.26 ppm): 7.87 (d, 1H, J=2.35Hz), 7.59 (dd, 1H, J=2.35, 8.22Hz), 7.14 (m, 2H), 6.86 (m, 2H), 5.82 (d, 1H, J=17.22Hz), 5.44 (d, 1H, J=11.35 Hz) (s = singlet, d = doublet, t = triplet, q = quartet, br = broad, m = multiplet). Molecular weight (M+H+): m/z calculated: 250.05, found: 250.1. Vinylated product (1.55g, 10 mmol) and 2-iodopropance (1.5ml, 15 mmol, 1.5 equiv) were dissolved in DMF (15ml), followed by adding K2CO3 (3.9g, 30 mmol) to DMF solution, then heated at 65°C overnight (15 hrs), monitored by HPLC until completed. After removing DMF, the mixture was washed with water, The aqueous layer was extracted with Et2O (2.x.100ml), and the combined organic layers were dried, and purified. The yellow solid product was obtained by purification. The product was purified by silica gel column chromatography to offer 1.69g of etherified product 4a (yield, : 82percent, purity: 98percent). It is certified that the ligand of Ru complex, 1HNMR (CDCl3: delta = 7.26 ppm): 7.42 (dd, 1H, J = 1.56, 7.82Hz), 7.29 (dd, 1H, J = 1.56, 7.83Hz), 7.02 (m, 2H), 5.73 (d, 1H, J = 17.60Hz), 5.56 (d, 1H, J = 11.34Hz), 4.43 (m, 1H), 1.32 (d, 6H, J = 6.26Hz). (M+H+): m/z calculated: 197.1, found: 197.2. Based on reference for the preparation of complexes (Hoveyda et al, J. Am. Chem. Soc. 2001, 123, 749), Ru complex 1a (290 mg, 0.30 mmol) and CuCl (75 mg, 0.75mmol) were added into a round-bottom flask under Ar atmosphere and dissolved in dichloromethane (DCM 5.0 ml). Ru complex ligand 4a (60mg, 0.30mmol) dissolved in DCM (1.0ml) was added into reaction system. The mixture was stirred for 30 min at room temperature, and then the reaction was completed. It is surprising that there were no any raw material in the solution; however, no any molecular ion peak was observed by Mass spectrograph (MS), which means corresponding complex product 5a can not be obtained during complexation reaction. And no any purple product of complex 5a was found and observed by TLC.
Catalysis of olefin metathesis including ring-closing of dienes, cross metathesis and ring-opening methathesis polymerizations (ROMP).
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