1271-51-8, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. Vinylferrocene, cas is 1271-51-8,the iron-catalyst compound, it is a common compound, a new synthetic route is introduced below.
In anhydrous THF (1 mL) was dissolved 6 molpercent Cu(OAc) 2 (10.9 mg,0.066 mmol) and 6.6 molpercent of ligand (R)-DTBM-SEGPHOS (78 mg,0.060 mmol). The mixture was stirred for 15 min at r.t., then DMMS(0.5 mL, 4 equiv, 4 mmol) was added dropwise and stirring was con-tinued for 10 min at the same temperature. The solution of amine 7(381 mg, 1.2 mmol) and vinylferrocene 4 (212 mg, 1 mmol) was thenadded by using Schlenk techniques to the tube containing the solu-tion of [L*CuH] complex. The reaction mixture was stirred at 40 ¡ãCovernight, then the mixture was diluted with EtOAc (5 mL) and 5percentsolution of Na 2 CO 3 (5 mL) was added dropwise. The solution was ex-tracted with EtOAc (3 ¡Á 25 mL), the collected organic layers werewashed with brine (25 mL), dried over Na 2 SO 4 , filtrated, and the sol-vent was removed under reduced pressure to afford the crude prod-uct. The crude product was purified by chromatography on SiO 2 (hex-anes/EtOAc, 30:1 + 1percent Et 3 N; R f = 0.4) to afford target product 8.Yield: 68 mg (18percent); orange solid; mp 62?65 ¡ãC; [alpha] D20 ?14.5 (c 1.00,CHCl 3 ); HPLC analysis (Chiralcel OD-H; hexane/ i PrOH, 99:1; 0.8mL/min; 254 nm) indicated 20percent ee: t R = 5.9 (major), 6.5 (minor) min.IR (ATR): 1234, 1103, 1068, 1022, 998, 822, 749, 728, 697, 514, 487cm ?1 .1 H NMR (600 MHz, CDCl 3 ): delta = 7.39 (d, J = 7.4 Hz, 4 H, -Ph), 7.31 (t, J =7.6 Hz, 4 H, -Ph), 7.23 (t, J = 7.3 Hz, 2 H, -Ph), 4.27?4.27 (m, 1 H, Fc),4.18?4.14 (m, 3 H, Fc), 4.02 (s, 5 H, Cp Fc ), 3.81 (q, J = 6.9 Hz, 1 H, H alpha ),3.53 (d, J = 14.1 Hz, 2 H, CH 2 -Ph), 3.36 (d, J = 14.1 Hz, 2 H, -CH 2 -Ph),1.47 (d, J = 6.9 Hz, 3 H, -CH 3 ).13 C NMR (151 MHz, CDCl 3 ): delta = 140.9 (2¡ÁC, Cq Ph ), 128.6 (4¡ÁC, -Ph),128.2 (4¡ÁC, -Ph), 126.7 (2¡ÁC, -Ph), 88.9 (Cq Fc ), 69.1 (-CH Fc ), 68.7 (5¡ÁC,Cp Fc ), 67.6 (-CH Fc ), 67.1 (-CH Fc ), 66.9 (-CH Fc ), 52.3 (2¡ÁC, -CH 2 -Ph), 52.2(-CH alpha ), 15.4 (-CH 3 ).HRMS (ESI): m/z calcd for [M + H + ] C 26 H 28 FeN + : 410.1571; found:410.1565.
The chemical industry reduces the impact on the environment during synthesis,1271-51-8,Vinylferrocene,I believe this compound will play a more active role in future production and life.
Reference£º
Article; Plevova, Kristina; Mudrakova, Brigita; ?ebesta, Radovan; Synthesis; vol. 50; 4; (2018); p. 760 – 763;,
Iron Catalysis in Organic Synthesis | Chemical Reviews
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