Tri-o-tolylphosphine → 5-[2-Benzyloxy-4-(3,3,3-trifluoropropyl)-phenyl]-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one

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Reaction Steps

To a solution of 1,1,1-trifluoro-3-iodopropane (0.088 mL, 0.75 mmol) in DMF (2 mL) is added Rieke zinc (0.9 mmol) and the mixture is stirred at RT for 5 h then P(o-tolyl)3 (22.8 mg, 15 mol %), Pd2(dba)3 (13.7 mg, 3 mol %) and 5-(2-benzyloxy-4-iodophenyl)-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one (272 mg, 0.5 mmol) is added and the mixture is stirred at RT for 18 h. The mixture is partitioned between EtOAc and 1N HCl and the organic phase is washed with brine and dried over sodium sulfate. The solvent is removed under reduced pressure and the residue is purified by column chromatography using a gradient of 0-15% EtOAc/hexane as eluent to give the title compound.

Provenance & Evidence