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Higher catalyst loadings are required to achieve complete conversion for these substrates, likely due to nonproductive, competitive oxidative addition at the aryl chloride, Thus, bromide or iodide substituents on the aromatic ring are presumably not compatible with our current protocol.
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Another possibility is that rotation about the carbonyl C-N bond of the palladium enolate into a reactive conformation is slow relative to the palladation event. For an analogous situation, see: Cohen, T.; McMullen, C. H.; Smith, K. J. Am. Chem. Soc. 1968, 90, 6866. We are grateful to a reviewer for making this suggestion.
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