4-Chlorobenzonitrile → (1,1'-Biphenyl)-4-carbonitrile

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Reaction Steps

According to General Procedure A, a mixture 4-chlorobenzonitrile (69 mg, 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 (5% Et2O in hexanes, silica gel) gave 51c (83 mg, 92%) as a colorless solid. 1H NMR (300 MHz, CDCl3) δ 7.69 (q, 4H, J=6 Hz), 7.61-7.57 (m, 2H), 7.52-7.40 (m, 3H); 13C NMR (75.5 MHz, CDCl3) δ 145.6, 139.1, 132.5, 129.0, 128.6, 127.6, 127.1, 118.8, 110.8.

Provenance & Evidence