Compound 4b

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Compound data: CIF

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

In a glovebox, p-tolylCOPd(P^tBu₃)Cl 4a (124 mg, 0.27 mmol) was weighed in a vial equipped with a magnetic stir bar. The complex was dissolved in 2 mL 1,2-dichloroethane. To this solution, AgOTf (76 mg, 0.30 mmol) was added and the mixture was stirred for 1 hour at room temperature. The resulting suspension was filtered through celite to afford a yellow solution. The solvent was removed in vacuo and the resulting oil was triturated with pentanes (1 mL). Solvent traces were removed under vacuum and product 4b was obtained as a dark yellow solid in 87% yield (134 mg, 0.23 mmol). ). ¹H NMR (500 MHz, CDCl₃): δ 8.11 (d, J = 8.3 Hz, 2H), 7.25 (d, J = 8.0 Hz, 2H), 2.41 (s, 3H), 1.50 (d, J = 13.3 Hz, 27H). ¹³C NMR (126 MHz, CDCl₃): δ 198.2 (d, J = 7.8 Hz), 145.3, 131.1, 130.0 (d, J = 18.5 Hz), 129.7, 118.6, 40.1 (d, J = 11.1 Hz), 32.2 (d, J = 3.5 Hz), 22.0. ³¹P NMR (162 MHz, CDCl₃): δ 80.7. Elemental analysis for C₂₁H₃₄F₃O₄PSPd: Theory 43.72 %C, 5.94 %H, 5.56 %S, Found 43.62 %C, 6.09 %H, 6.23 %S. Crystals of 4b were grown for X-ray diffraction by vapor diffusion of pentane into a solution of the complex in 1,2-dichloroethane (50 mg in 250 µL) at -33 ºC for 3 days which resulted in dark yellow crystals. The X-ray crystal structure is available at the Cambridge Crystallographic Data Centre (CCDC) under the deposition number 1554343.