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Air Stable Diaminophosphine Oxide Ligands for Transition Metal Catalyzed Cross-Coupling Reactions

These air stable diaminophosphine oxide ligands find effective use1) in palladium-catalyzed Suzuki type reactions of readily available but potentially difficult and challenging aryl chloride substrates.1)
The ligands facilitate the activation of C-F bonds in the Ni-catalyzed Kumada cross coupling reaction2) and exhibit superior catalytic activity as compared to all earlier known protocols.
These sophisticated ligands provide a competent alternative to the use of traditional palladium/triarylphosphane catalysts as well as electron rich alkyl-substituted tertiary phosphines and secondary phosphine oxides in transition metal catalyzed cross coupling reactions.
Typical procedure: 2)
A solution of [Ni(acac)2] (7 mg, 0.03 mmol, 3 mol%) and diaminophosphine oxide 2 (13 mg, 0.03 mmol, 3 mol%) in dry THF (0.5 mL) is stirred for 10 min at ambient temperature under N2. 1-Fluoronaphthalene (148 mg, 1.01 mmol) is added, and the solution is stirred for 5 min. Thereafter, 4-methoxyphenylmagnesium bromide (0.5 M in THF, 3.0 mL, 1.50 mmol) 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 (75 mL×2). 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→100:1) to yield 4-(1-naphthyl)anisole as a pale yellow solid (223 mg, 94%).

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