1,3-Bis(2,6-diisopropylphenyl)-1,3,2-diazaphospholidine 2-Oxide

Typical procedure: A solution of [Ni(acac)2] (7 mg) and the Phosphine oxide B3479 (13 mg) in dry THF (0.5 mL) is stirred for 10 min at ambient temperature under N2. 1-Fluoronaphthalene (148 mg) is added, and the solution is stirred for 5 min. Thereafter, phenylmagnesium bromide (0.5 M in THF, 3.0 mL) is added. The resulting dark solution is stirred at ambient temperature for 15 h. Et2O (75 mL) and H2O (75 mL) are added to the reaction mixture. The separated aqueous phase is extracted with Et2O (2 x 75 mL). The combined organic layers are dried over MgSO4 and concentrated in vacuo. The remaining residue is purified by column chromatography on silica gel (n-pentane/Et2O, 300:1, 200:1, 150:1, and 100:1) to yield 4-(1-naphthyl)anisole as a pale yellow solid (223 mg, 94%).