Silver-Catalyzed Regioselective Phosphorylation of -Quinone Methides with P(III)-Nucleophiles.

A simple and efficient method for the silver-catalyzed regioselective phosphorylation of -quinone methides (-QMs) with P(III)-nucleophiles (P(OR), ArP(OR), ArP-OR) has been established via Michaelis-Arbuzov-type reaction. A broad range of P(III)-nucleophiles and -quinone methides are well tolerated under the mild conditions, giving the expected diarylmethyl-substituted organophosphorus compounds with good to excellent yields. Moreover, a series of corresponding enantiomers can be obtained by employing dialkyl arylphosphonite (ArP(OR)) as substrates. The control experiments and P NMR tracking experiments were also performed to gain insights for the plausible reaction mechanism. This protocol may have significant implications for the formation of C()-P bonds in Michaelis-Arbuzov-type reactions.