We went on to examine the generality of the cross-nucleophile coupling of silyl enol ethers with a variety of other nucleophiles (Schemes 2b and 2c). Using both electron-poor and electron-rich benzoic acids as nucleophiles, acarboxylate-carbonyl compounds 8a-8c were obtained in excellent yields (80-98%). When alcohols were tested as nucleophiles under otherwise identical reaction conditions, complex mixtures of unidentified by-products were formed. However, these difficulties were overcome by modifying the protocol; first silyl enol ether 1a was treated with I(III) reagent 2c. This was followed by the addition of the alcohol nucleophile (Method B). Using this procedure, a-phenolate 8d was obtained in 66% yield. Thiols were also well tolerated, and thiophenol gave 8e in 60% yield using the standard procedure described above (i.e., Method A), and in 82% yield using Method B. An alkylsubstituted thiol gave a quantitative yield (8f, Method B). Importantly, primary amines are also well tolerated, and benzylamine derivative 8g was obtained in 67% yield when using Method B. Cyclopropylamine reacted smoothly to give 8h in 40% yield, which could be improved to 60% by using Method B. Piperidine gave a-aminoketone 8i in 53% yield, and morpholine derivative 8j was obtained in 60% yield. Interestingly, carbon nucleophiles such as malonates also reacted smoothly, and 8k was formed in 50% yield. a-Azido carbonyl compound 8l was obtained in 50% isolated yield.