Efficient Activation of Acetals, Aldehydes, and Imines toward Silylated Nucleophiles by the Combined Use of Catalytic Amounts of [Rh(COD)Cl]2 and TMS-CN under Almost Neutral Conditions

In the presence of a catalytic amount of a transition metal compound such as [Rh(COD)Cl]2, Co(acac)2, or NiCl2, trimethylsilyl cyanide smoothly reacts with acetals to form α-methoxy carbonitriles in good yields. In the coexistence of catalytic amounts of [Rh(COD)Cl]2 and TMS-CN, silyl enol ethers or ketene silyl acetals react with acetals, aldehyes, or imines to yield the corresponding coupling products in good yields under almost neutral conditions.