* 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.
With C126H91CoN12O10; tetrabutyl-ammonium chloride In dichloromethane at 25℃; for 96 h; Autoclave
General procedure: All reactions were conducted in a 100 mL stainless steel autoclave equipped with a magnetic stir bar, and submerged in anoil bath. The required catalyst, tetrabutylammonium chloride (TBAC) as the co‐catalyst, epoxide, and CH2Cl2 were added tothe reactor in turn. The reactor was then charged with CO2 and vented three times, and finally pressurized with CO2 to 1.0 MPa. The contents were then stirred at room temperature for an established period that depended on the selected substrate and catalyst, after which the reactor was carefully discharged to atmospheric pressure. The yield of cyclic carbonate was determinedby the subtraction method or by comparison betweenthe integral areas obtained by 1H NMR spectroscopy for thecyclic carbonate and epoxide.
31.6%
With C126H91CoN12O10; tetrabutyl-ammonium chloride In dichloromethane at 25℃; for 96 h; Autoclave
General procedure: All reactions were conducted in a 100 mL stainless steel autoclave equipped with a magnetic stir bar, and submerged in anoil bath. The required catalyst, tetrabutylammonium chloride (TBAC) as the co‐catalyst, epoxide, and CH2Cl2 were added tothe reactor in turn. The reactor was then charged with CO2 and vented three times, and finally pressurized with CO2 to 1.0 MPa. The contents were then stirred at room temperature for an established period that depended on the selected substrate and catalyst, after which the reactor was carefully discharged to atmospheric pressure. The yield of cyclic carbonate was determinedby the subtraction method or by comparison betweenthe integral areas obtained by 1H NMR spectroscopy for thecyclic carbonate and epoxide.
38.8 % ee
at 25℃; for 25 h; Autoclave
General procedure: A solution of freshly prepared SalenCo(III)Y (0.1 mmol) andepoxide (100 mmol) was introduced into a 100 mL stainless-steelautoclave, which was purged three times and charged with CO2to 1.2 MPa. The reaction mixture was stirred at room temperature.When the pressure of reactor was fall down to a presetting value, itwas then vented carefully. After removing the excess epoxide, theresidue was weighed to measure the conversion of epoxide, chiralcyclic carbonate (R = Me, Et, CH2Cl) was distilled under vacuum as asa colorless liquid or it (R = Ph, PhOCH2) was obtained by columnchromatography through a short silica–gel column to yield whitesolid product (ethyl acetate/petroleum ether = 5:1).
Reference：
[1] Dalton Transactions, 2013, vol. 42, # 27, p. 9930 - 9937
[2] Chinese Journal of Catalysis, 2018, vol. 39, # 5, p. 997 - 1003
[3] Chinese Journal of Catalysis, 2018, vol. 39, # 5, p. 997 - 1003
[4] Journal of the American Chemical Society, 2004, vol. 126, # 12, p. 3732 - 3733
[5] Chemical Communications, 2004, # 14, p. 1622 - 1623
[6] Tetrahedron Letters, 2007, vol. 48, # 2, p. 297 - 300
[7] Tetrahedron Letters, 2008, vol. 49, # 46, p. 6589 - 6592
[8] Advanced Synthesis and Catalysis, 2009, vol. 351, # 9, p. 1325 - 1332
[9] Advanced Synthesis and Catalysis, 2009, vol. 351, # 9, p. 1325 - 1332
[10] Green Chemistry, 2009, vol. 11, # 7, p. 935 - 938
[11] Green Chemistry, 2009, vol. 11, # 7, p. 935 - 938
[12] Science China Chemistry, 2011, vol. 54, # 7, p. 1044 - 1050
[13] Science China Chemistry, 2011, vol. 54, # 7, p. 1044 - 1050
[14] Catalysis Science and Technology, 2013, vol. 3, # 10, p. 2661 - 2667
[15] Journal of Molecular Catalysis A: Chemical, 2016, vol. 411, p. 34 - 39
[16] RSC Advances, 2016, vol. 6, # 4, p. 3243 - 3249
[17] Chemical Communications, 2017, vol. 53, # 79, p. 10930 - 10933
[18] Chemical Communications, 2017, vol. 53, # 79, p. 10930 - 10933
[19] Chinese Journal of Catalysis, 2018, vol. 39, # 5, p. 997 - 1003
2
[ 124-38-9 ]
[ 75-56-9 ]
[ 51260-39-0 ]
[ 15448-47-2 ]
[ 16606-55-6 ]
Yield
Reaction Conditions
Operation in experiment
66.7 % ee
at 25℃; for 8 h; Autoclave
General procedure: Catalyst of (S,R,R,S)-ZSS-2b (631 mg, 0.1 mmol), cocatalyst of tetrabutylammonium fluoride (TBAF, 0.0522 g, 0.2 mmol), and racemic propylene oxide (PO, 7 mL, 100 mmol) were introduced into a 100-mL stainless steel autoclave to form a brown solution. The reactor was purged thrice with carbon dioxide, and charged it to 0.8 MPa. Then, the asymmetric catalytic reaction took place at room temperature. After some time, the pressure in the reactor decreased to an expected value, and it was vented to terminate the reaction. After removing the unreacted epoxide, chiral cyclic carbonate (R=Me, Et, CH2Cl), weighed to calculate the yield of cyclic carbonate, was distilled under vacuum as a colorless liquid or it (R=Ph, PhOCH2) was obtained by column chromatography through a short silica gel column (ethyl acetate:petroleum ether = 5:1).
General procedure: Catalyst of (S,R,R,S)-ZSS-2b (631 mg, 0.1 mmol), cocatalyst of tetrabutylammonium fluoride (TBAF, 0.0522 g, 0.2 mmol), and racemic propylene oxide (PO, 7 mL, 100 mmol) were introduced into a 100-mL stainless steel autoclave to form a brown solution. The reactor was purged thrice with carbon dioxide, and charged it to 0.8 MPa. Then, the asymmetric catalytic reaction took place at room temperature. After some time, the pressure in the reactor decreased to an expected value, and it was vented to terminate the reaction. After removing the unreacted epoxide, chiral cyclic carbonate (R=Me, Et, CH2Cl), weighed to calculate the yield of cyclic carbonate, was distilled under vacuum as a colorless liquid or it (R=Ph, PhOCH2) was obtained by column chromatography through a short silica gel column (ethyl acetate:petroleum ether = 5:1).
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