7650-91-1 Benzyldiphenylphosphine 603920, achiral-phosphine-ligands compound, is more and more widely used in various fields.
7650-91-1, Benzyldiphenylphosphine is a chiral-phosphine-ligands compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated
7650-91-1, To a white suspension of P(CH2C6H5)Ph2 (2.08 g, 7.53 mmol) in toluene (20 mL) in a 300 mL Kjeldahl flask, added dropwise a yellow solution of 3c (1.83 g, 7.17 mmol) in toluene (20 mL) at 25 oC. The combined mixture became a clear yellow solution immediately. After stirring for 15 minutes effervescence was observed. The solution was stirred for 4 hours and it remained a clear yellow solution. Removal of the solvent under vacuum afforded a yellow viscous material which was redissolved with CH2Cl2 (20 mL). The resulting clear yellow solution was transferred via cannula over to a suspension of [PyH][BF4] (1.29 g, 7.17 mmol) in CH2Cl2 (20 mL). The Kjeldahl flask was rinsed with CH2Cl2 (2×20 mL) and the rinsing solution was transferred to the reaction flask via cannula. Pyridine (0.9 mL, 10.8 mmol) was added to the white suspension in CH2Cl2 and the reaction mixture was refluxed for 12 hours. After cooling the reaction to 25 oC, a clear yellow solution was observed and the volatiles were removed under vacuum. The resulting viscous residue was washed with diethyl ether (4 x 40 mL) to give a yellow gum. The gum was purified by column chromatography using silica gel (80 g) and CH2Cl2. The column was eluted with CH2Cl2 (200 mL), CH2Cl2-MeOH 98:2 (500 mL), CH2Cl2-MeOH 95:5 (500 mL), CH2Cl2-MeOH 90:10 (500 mL), and CH2Cl2-MeOH 80:20 (500 mL). The fractions (100 mL) were analyzed by UV-Vis, and those that contained the product were combined and dried under vacuum, affording white foam. The foam was treated with CH2Cl2 (100 mL) and diethyl ether (300 mL) to afford a white precipitate. Filtration of the precipitate followed by diethyl ether washes (40 mL) afforded 17 (2.17g, 66%) as a white powder. 1H NMR ((CD3)2SO): delta 9.66 (d, JPH = 10.4, 1H, -P=NH-), 7.97 (m, 4H, 2,6-CH of -(C6H5)2P=NH-), 7.82 (m, 2H, 4-CH of -(C6H5)2P=NH-), 7.70 (m, 4H, 3,5-CH of -(C6H5)2P=NH-), 7.54 (s, 1H, -CH of C6H3SO3), 7.20-7.28 (m, 3H, 2,6- and 4-CH of -C6H5CH2P=NH-), 7.10 (m, 3,5-CH of -C6H5CH2P=NH-), 6.91 (dd, J = 8.0, 1.6, 1H, 4-CH of -C6H3SO3-), 6.64 (d, J = 8.0, 1H, 3-CH of -C6H3SO3-), 5.00 (d, JPH = 14.0, -CH2P=NH-), 2.21 (s, 3H, 5-CH3 of -C6H3SO3-). 1H NMR (CD2Cl2): delta 9.68 (d, JPH = 10.4, 1H, -P=NH-), 7.71-7.85 (m, 7H, 6-CH of -C6H3SO3-, 3,5-CH of -(C6H5)2P=NH-, and 2,6-CH of -C6H5CH2P=NH-), 7.62 (, m, 4H, 2,6-CH of -C6H5CH2P=NH ), 7.28 (m, 1H, 4-CH of -C6H5CH2P=NH), 7.20 (t, J = 7.6, 3,5-CH of -C6H5CH2P=NH-), 6.96 (m, 2H, 4-CH of -(C6H5)2P=NH-), 6.79 (dd, J = 8.4, 2.0, 1H, 4-CH of -C6H3SO3-), 6.34 (d, J = 8.4, 1H, 3-CH of -C6H3SO3-), 4.27 (d, JPH = 14.0, -CH2P=NH-), 2.23 (s, 3H, 5-CH3 of -C6H3SO3-). 31P NMR ((CD3)2SO): delta 35.9. 31P NMR (CD2Cl2): delta 36.1. 13C NMR ((CD3)2SO): delta 137.0 (d, JPC = 7.8), 135.6 (d, JPC = 3.1, para-CH of -(C6H5)2P=NH-), 133.1 (d, JPC = 10.8, ortho-CH of -(C6H5)2P=NH-), 132.7, 132.4, 131.1, 131.0 (d, JPC = 3.1), 130.4 (d, , JPC = 10.8, meta-CH of -(C6H5)2P=NH-), 129.3 (d, JPC = 3.1), 128.5, 128.4, 128.0 (d, JPC = 10.0, ipso C of -C6H5CH2P=NH-), 120.5 (d, JPC = 96.8, ipso C of -(C6H5)2P=NH-), 119.5 (d, JPC = 3.9), 30.9 (d, JPC = 56.5, -CH2P=NH-), 20.5. Anal. Calcd for C26H24NO3PS: C, 67.66; H, 5.24; N, 3.03. Found: C, 67.86; H, 5.33; N, 2.91.
7650-91-1 Benzyldiphenylphosphine 603920, achiral-phosphine-ligands compound, is more and more widely used in various fields.
Reference£º
Article; Burns, Christopher T.; Shang, Suisheng; Thapa, Rajesh; Mashuta, Mark S.; Tetrahedron Letters; vol. 53; 36; (2012); p. 4832 – 4835;,
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