4-Chlorotoluene → 4-Methylbiphenyl

Participants

Reaction Steps

According to General Procedure A, a mixture of 4-chlorotoluene (59 μL, 0.50 mmol), phenylboronic acid (91 mg, 0.75 mmol), CsF (228 mg, 1.50 mmol), Pd(OAc)2 (2 mg, 0.01 mmol) and 12f (8 mg, 0.02 mmol) in 1,4-dioxane (2.5 mL) was heated to reflux, cooled and filtered. Evaporation of the solvent under reduced pressure and column chromatography of the pre-adsorbed crude material (1% Et2O in hexane silica gel) gave 51f (47 mg, 56%) as a colorless solid. 1H NMR (300 MHz, CDCl3) δ 7.59 (d, 2H, J=7.8 Hz), 7.51 (d, 2H, J=7.8 Hz), 7.44 (d, 2H, J=7.8 Hz), 7.35-7.24 (m, 3H), 2.41 (s, 3H); 13C NMR (75.5 MHz, CDCl3) δ 141.1, 138.3, 137.0, 129.5, 128.7, 127.0, 126.9, 21.1.

Provenance & Evidence