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Refluxing water is a good solvent for the coupling reactions of aryl and heteroaryl chlorides with phenylboronic acid (see scheme; FG=functional group). The reactions use oxime-derived palladacycles 1 as thermally stable catalysts, potassium carbonate as base, and tetrabutylammonium bromide (TBAB), and can be carried out in the presence of air.
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Botella et al. (2002) studied this question.
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