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I know that benzene diazonium chloride couples with phenol and aniline. One N atom of the diazonium ion forms a bond with the carbon at the para postion of the ring. That made me think, can a coupling reaction occur between benzene diazonium chloride and say, benzene or chlorobenzene or any compound that has a phenyl group?Ann if not, then what kind of compounds will it react with?

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    $\begingroup$ Only strongly activated rings - primarily what you mentioned. If it could react with benzene, you'd probably see such example. $\endgroup$
    – Mithoron
    Feb 24 at 18:59

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