We observed that the product of a Buchwald-Hartwig coupling reaction extracted from the organic phase easily, relative to the starting aryl bromide as the pH was lowered. This was surprising given the similarity of their p K's. The product's extraction curve was also significantly steeper than expected. A consideration of the relevant equilibria, including all three of the product's p K's, led to a general model for the liquid-liquid extraction behavior of ionizable molecules. This model predicts the observed, useful extraction behavior.
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| http://dx.doi.org/10.1021/acs.joc.8b00309 | DOI Listing |
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