Triphenylphosphine → 4-(4-Chlorobenzyl)thiophene-2-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

A solution mixture of Pd(OAc)2 (144 mg, 0.64 mmol) and triphenylphosphine (TPP) (136 mg, 0.52 mmol) were weighed into a vial, dissolved in acetonitrile and transferred into a 40 mL Wheaton vial containing diethyl 4-chlorobenzyl phosphate (Org. Lett. 2005, 7, 4875-4878; 3.08 g, 11.6 mmol), 5-formylthiophen-3-ylboronic acid (2.0 g, 12.8 mmol), K3PO4 (2.72 g, 12.8 mmol) and a stir-bar. Nitrogen gas was bubbled through the mixture. The vial was closed tightly and heated to 90° C. and vigorously stirred for 16 h. The reaction was diluted with water and extracted with dichloromethane (DCM) (3×100 mL). The combined extracts were washed with brine, dried over Na2SO4, filtered and concentrated. Purification by flash chromatography (Isco CombiFlash) (0-20% heptane/EtOAc) yielded 4-(4-chlorobenzyl)thiophene-2-carbaldehyde: 835 mg, 28% yield. 1H NMR (400 MHz, CDCl3) δ ppm: 10.10 (d, 1H), 7.80 (d, 1H), 7.63 (m, 1H), 7.55 (m, 2H), 7.40 (m, 2H), 4.23 (s, 2H).

Provenance & Evidence