With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1160861-53-9,Di-tert-butyl(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine,as a common compound, the synthetic route is as follows.
A dry Schlenk flask is charged with 183 mg (0.50 mmol) of [(allyl)PdCl]2 and 257 mg (1.0 mmol) of silver trifluoromethanesulfonate. A second dry Schlenk flask is fitted with a Schlenk frit and is charged with 485 mg (1.0 mmol) of tBuBrettPhos. The flasks are evacuated and backfilled with nitrogen. This evacuation/backfill cycle was repeated a total of three times. 10 mL of anhydrous THF is added to the first flask and the mixture is stirred for 30 min at room temperature (rt) while protecting from light. The mixture from flask one is then transferred via cannula through the Schlenk frit into the second flask to remove the AgCl. The frit is rinsed with an additional 10 mL of anhydrous THF. The mixture is stirred at room temperature for 2 hours, followed by the slow addition of 30 mL of hexanes to obtain a pale yellow precipitate. It is filtered, washed (2*10 mL of hexanes) and dried in vacuo to give 653 mg (0.84 mmol, 84%) of analytically pure (pi-allyl)Pd(tBuBrettPhos)OTf as a slightly yellow solid; 1H NMR (400 MHz, CDCl3, delta): 7.45 (d, J=1.8 Hz, 1H), 7.28 (d, J=1.7 Hz, 1H), 7.07 (dd, J=2.9 Hz, 9.0 Hz, 1H), 6.96 (dd, J=2.9 Hz, 8.9 Hz, 1H), 5.52 (sept, J=7.1 Hz, 1H), 4.39 (app d, J=6.3 Hz, 1H), 3.83 (s, 3H), 3.35 (dd, J=9.2 Hz, 13.9 Hz, 1H), 3.32 (s, 3H), 2.97 (sept, J=6.9 Hz, 1H), 2.78 (app d, J=12.4 Hz, 1H), 2.54 (sept, J=6.7 Hz, 1H), 2.30-1.12 (m, 2H), 1.45-1.27 (m, 24H), 1.24 (dd, J=6.9 Hz, 11.8 Hz, 6H), 0.87 (d, J=6.9 Hz, 3H), 0.70 (d, J=6.9 Hz, 3H); 13C NMR (100 MHz, CDCl3, delta): 156.3, 154.6 (2 peaks), 154.5, 152.2, 151.5, 136.5, 136.2, 125.8, 125.7, 125.6, 125.4, 125.2, 122.6, 119.7, 119.6, 119.4, 116.2, 115.5 (2 peaks), 112.8 (2 peaks), 112.0 (2 peaks), 99.8, 99.5, 58.4 (2 peaks), 54.7, 54.6, 39.9, 39.8, 39.3, 39.1, 34.0, 32.1, 32.0, 31.9, 31.7, 31.6 (2 peaks), 25.7, 25.5, 24.6, 24.5, 24.2 [Observed complexity due to C-F and C-P coupling]; 19F NMR (372 MHz, CDCl3, delta): -77.9 (s, 3F); 31P NMR (162 MHz, CDCl3, delta): 86.2; Anal. calcd. for C35H54O5F3PSPd: C, 53.81; H, 6.97. Found C, 53.81; H, 7.10., 1160861-53-9
As the paragraph descriping shows that 1160861-53-9 is playing an increasingly important role.
Reference£º
Patent; Johnson Matthey Public Limited Company; Colacot, Thomas; Jon Deangelis, Andrew; (66 pag.)US9777030; (2017); B2;,
Phosphine ligand
Chiral phosphine ligands in asymmetric synthesis. Molecular structure and absolute configuration of (1,5-cyclooctadiene)-(2S,3S)-2,3-bis(diphenylphosphino)butanerhodium(I) perchlorate tetrahydrofuran solvate