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The copper catalyzed coupling reaction of O-H and N-H compounds with aryl halides ArX leads to the replacement of the hydrogen by the aryl group:1 Addition of bases such as K2CO3 and KOH as the acceptor of HX released is necessary for the reaction to proceed, and sometimes, instead of the O-H and N-H compounds, use of their salts (e.g., potassium phenolate and potassium phthalimide) as the starting material is required.
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Takakazu Yamamoto (1979) studied this question.
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