As a common heterocyclic compound, it belong copper-catalyst compound,[1,3-Bis(2,6-diisopropylphenyl)imidazol-2-ylidene]copper chloride,578743-87-0,Molecular formula: C27H36ClCuN2,mainly used in chemical industry, its synthesis route is as follows.,578743-87-0
General procedure: To an oven-dried screwed 20 mL vial were added (NHC)CuCl (c7 or c8, 0.2 mmol) suspended in dry THF (3 mL); in another vial, [tBu3PN]Li (1b, 42.3 mg, 0.95 eq.) was also dissolved in dry THF (3 mL), then the vial was put into glove-box fridge (-35 C) for one hour. Then the cold mixture was dropped into the (NHC)CuCl/THF suspension slowly under stirring and the suspension was turned into clear solution as the lithium salt added. After addition, the reaction mixture was kept at room temperature in glove box for 13 hours. After the reaction was completed, the volatile was removed under vacuum and dry hexane or pentane (7 mL) was added into the formed oily residue. The suspension obtained was kept stirring for another 15 mins at room temperature, then filtered through a short pad of neutral celite to get rid of precipitate. The filtrate was cooled down in the fridge (-35 C) for 3-4 hours to remove the unreacted lithium salt 1b further. Repeated once again to get the clear hexane or pentane filtrate. The filtrate was evaporated until white crystallized solid was formed, which is the catalytic active species (3 or 4). IPrCuCl (c7, 97 mg, 0.2 mmol); Obtain IPrCuNPtBu3 (3, 99 mg, 78%) as Colorless Solid; 1H NMR (C6D6, 600 MHz) delta 7.26-7.21 (br, m, 4H, m-ArH), 7.17-7.14 (br, m, 2H, p-ArH), 6.40 (s, 2H, NCH=), 2.83 (sep, 4H, J = 6.6 Hz, CH(CH3)2), 1.61 (d, 12H, J = 6.6 Hz, CH(CH3)2), 1.37 (d, 27H, J(PH) = 10.8 Hz, P(C(CH3)3)3), 1.20 (d, 12H, J = 6.6 Hz, CH(CH3)2); 13C NMR (C6D6, 151 MHz) delta 146.18, 136.50, 130.42, 128.68, 124.42, 122.05, 40.78, 40.49, 31.01, 29.33, 25.04, 24.42; 31P NMR (C6D6, 243 MHz) delta 26.35 (s); Elemental analysis calcd for [C39H63CuN3P+0.67 THF]: C, 69.84; H, 9.61; N, 5.86. Found: C, 69.48; H, 9.90; N, 6.19.
With the synthetic route has been constantly updated, we look forward to future research findings about [1,3-Bis(2,6-diisopropylphenyl)imidazol-2-ylidene]copper chloride,belong copper-catalyst compound
Reference£º
Article; Bai, Tao; Yang, Yanhui; Han, Chao; Tetrahedron Letters; vol. 58; 15; (2017); p. 1523 – 1527;,
Copper catalysis in organic synthesis – NCBI
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”