Tetrahydrofuran → HCID 15302813, compound

Participants

Reaction Steps

An oven-dried Schlenk tube containing a stir bar was charged with Pd2(dba)3 (6.9 mg, 0.0075 mmol, 1.5 mol %), ligand (0.018 mmol, 3.6 mol %), and NaOt-Bu (65 mg, 0.65 mmol). The Schlenk tube was evacuated and back filled with argon. THF (2 mL) was added followed by aryl halide (0.5 mmol), ketone (0.6 mmol or 1.0 mmol), and additional THF (1 !mL). The resulting red mixture was heated under argon at 70° C. until the starting halide had been consumed as judged by GC analysis. The Schlenk tube was cooled to room temperature, and diethyl ether (25 mL) and H2O (25 mL) were added. The aqueous layer was separated and extracted with diethyl ether (25 mL). The organic layers were combined, washed with brine (40 mL), dried over MgSO4, filtered, and concentrated. The crude product was then purified by flash chromatography on silica gel. Using 0.6 mmol of ketone and BINAP gave 107 mg (89% yield) of a colorless oil. 1H NMR (CDCl3, 250 MHz) δ 7.92-7.96 (m, 2H), 7.31-7.44 (m, 3H), 7.19 (t, J=7.0 Hz, 1H), 6.82-6.88 (m 2H), 6.72 (dd, J=8.3, 2.3 Hz, H), 4.64 (q, J=6.8 Hz, 1H), 3.73 (s, 3H), 1.52 (d, J=6.8 Hz, 3H); 13C NMR (CDCl3, 250 MHz) 5200.1, 150.0, 143.0, 136.6, 132.7, 129.9, 128.7, 128.4, 120.2, 113.5, 112.2, 55.1, 47.9, 19.3; IR (neat, cm−1) 2975, 2932, 1682, 1597, 1583. Anal Calcd for C16H602: C, 79.97; H, 6.71. Found: C, 79.89; H, 6.62.

Provenance & Evidence