Compound 2a

View in PubChem | MDL Molfile | Chemdraw file

Compound data: 1H NMR

Compound data: 13C NMR

Compound data: 31P NMR

Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.

General procedure: To a 40 mL vial charged with a stir bar, 2,2’-diphenol (1.0 equiv.) was dissolved in dry CH₃CN (500 mg/10 mL), dry Et₃N (4.0 equiv.) was added. Chlorodiisopropylphosphine (2.1 equiv.) was then added dropwise to the reaction mixture at room temperature. After addition of chlorodiisopropylphosphine, the vial was sealed and heated to 70 ^oC overnight. After the reaction was completed, the reaction mixture was extracted with pentane or hexane in glovebox and concentrated to give the corresponding phosphinites which were pure enough for the C-C activation reactions. For some phosphinites which are insoluble in pentane or hexane, CH₃CN was removed after the reaction, dry benzene was used to wash the residue, the combined benzene was concentrated to give the corresponding phosphintes which were pure enough for the C-C activation reactions. (The phosphinites were sensitive to moisture, and must be stored in glovebox. HRMS can’t be obtained due to their moisture sensitive property). Phosphinite 2a was synthesised following the general procedure outlined above. White solid (54% yield), m.p. 60 – 63 ^oC. ¹H NMR (500 MHz, CD₂Cl₂) δ 6.70 (s, 2H), 6.65 (s, 2H), 3.81 (s, 6H), 2.29 (s, 6H), 1.64 (br, 4H), 0.93 – 0.86 (m, 24H); ¹³C NMR (126 MHz, CD₂Cl₂) δ 151.0, 143.3, 131.9, 131.2, 124.4, 112.9, 55.7, 28.4 (d, J = 21.5 Hz), 20.8, 17.1 (d, J = 16.8 Hz), 17.0; ³¹P NMR (202 MHz, CD₂Cl₂) δ 162.41. IR (film, cm^-1) 2950, 2866, 1583, 1463, 1358, 1382, 1145, 1051.