2-DI-TERT-BUTYLPHOSPHINO-2',4',6'-TRIISOPROPYLBIPHENYL

White to pale yellow

1L three bottles, To a solution of 32.5 g of 2, 4, 6-triisopropylbromobenzene, 5.6 g of magnesium turnings and 300 mL of anhydrous THF, 20 g of o-chlorobromobenzene was dropwise added, 2, 4, 6-triisopropyl-2-bromobiphenyl Grignard reagent, Refluxed for 2 hours, Down to room temperature, 2.4 g of tetrakis (triphenylphosphine) palladium was added, Stirred for 30 minutes, 18.8 g of di-tert-butylphosphonium chloride was added dropwise at room temperature, The reaction was refluxed for 5 hours.And the mixture was added dropwise to the reaction solution under ice-water bath200 mL of saturated aqueous ammonium chloride was quenched, Liquid separation, The organic phase is dissolved, Add methanol crystallization, And filtered to obtain 41.7 g of white 2-di-tert-butylphosphine-2, 4, 6-triisopropylbiphenyl, Yield 94percent.1L three bottles, To a solution of 32.5 g of 2, 4, 6-triisopropylbromobenzene, 5.6 g of magnesium turnings and 300 mL of anhydrous THF, 20 g of o-chlorobromobenzene was dropwise added, 2, 4, 6-triisopropyl-2-bromobiphenyl Grignard reagent, Refluxed for 2 hours, Down to room temperature, 2.4 g of tetrakis (triphenylphosphine) palladium was added, Stirred for 30 minutes, 18.8 g of di-tert-butylphosphonium chloride was added dropwise at room temperature, The reaction was refluxed for 5 hours.And the mixture was added dropwise to the reaction solution under ice-water bath200 mL of saturated aqueous ammonium chloride was quenched, Liquid separation, The organic phase is dissolved, Add methanol crystallization, And filtered to obtain 41.7 g of white 2-di-tert-butylphosphine-2, 4, 6-triisopropylbiphenyl, Yield 94%.Under the protection of argon, a reaction solvent of 1 L of toluene was added to the dry reactor.Then add di-tert-butylphosphine (146 g, 1 mol), O-dibromobenzene (212 g, 0.9 mol), Bis[di-tert-butyl(4-dimethylaminophenyl)phosphine]palladium(0) (3.2 g, 0.005 mol) and sodium carbonate (530 g, 5 mol), then warmed to 80 C for 8 hours.After the reaction solution is cooled to 20-30oC, Add 2, 4, 6-triisopropylbenzeneboronic acid (273 g, 1.1 mol) directly to the system.Then heat up to 100 oC for 12 hours; then add water to quench the reaction, extract, dry, The solvent was distilled off under reduced pressure and the crystals were crystallized from methylene chloride to give 2-(di-tert-butylphosphino)-2', 4', 6'-triisopropylbiphenyl 364 g, yield 86%.[(i13-Indeny1)Pd(.i-OTf)j2 (0.10 g, 0.135 mmol) and tBUXPhOS (0.115 g, 0.270 mmol) were added to a 20 mL vial equipped with a flea stir bar. THF (10 mL) was added to the vial and a red homogenous mixture was observed. The mixture was stirred for one hour at room temperature, at which time the solvent was removed under reduced pressure. The red oil wastitrated with pentane to yield a dark red solid. Yield: 0.197 g, 92%. 1H NMR (CDCl3, 500MHz): 7.83 (t, J = 5.9 Hz, 1H), 7.52-7.49 (m, 2H), 7.43 (t, J = 5.7 Hz, 1H), 7.21 (s, 1H), 7.14(d, J = 5.5 Hz, 1H), 7.05 (t, J = 6.0 Hz, 1H), 6.97 (d, J = 6.7 Hz, 1H), 6.77-6.73 (m, 2H), 6.65(dd, J = 6.0, 3.1 Hz, 1H), 6.40 (s, 1H), 4.35 (d, 5.6 Hz, 1H), 3.20 (sept, J = 6.5 Hz, 1H), 2.26(sept, J = 6.4 Hz, 1H), 2.18 (sept, J = 6.5 Hz, 1H), 1.54-1.47 (m, 9H), 1.45 (d, J = 5.7 Hz, 9H), 1.41 (d, J = 5.6 Hz, 9H), 0.83-0.79 (m, 6H), 0.59 (d, J = 5.4 Hz, 3H) ppm. 13C{1H} NMR(101 MHz, CDCl3): 153.18, 148.57, 145.52, 145.32, 135.72, 134.25, 133.10, 132.99, 131.51, 129.61, 128.16, 127.96, 126.68, 126.07, 122.34, 121.45, 119.36, 116.82, 116.60, 114.60, 34.22, 32.13, 32.05, 31.22, 31.17, 30.41, 30.36, 27.89, 26.11, 25.50, 25.22, 24.77, 23.65, 23.24 ppm. 31P{1H} NMR (CDCl3 100 MHz): 82.57 ppm. 19F NMR (376 MHz, CDCl3): -77.92 ppm.

suzuki reaction

Molecular Weight:424.6
XLogP3:8.5
Rotatable Bond Count:7
Exact Mass:424.32588843
Monoisotopic Mass:424.32588843
Heavy Atom Count:30
Complexity:486
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes