New Gilman-type lithium cuprate from a copper(II) salt: synthesis and deprotonative cupration of aromatics
Résumé
Deprotonative cupration of aromatics including heterocycles (anisole, 1,4-dimethoxybenzene, thiophene, furan, 2- fluoropyridine, 2-chloropyridine, 2-bromopyridine and 2,4-dimethoxypyrimidine) was realized in tetrahydrofuran at room temperature using the Gilman-type amido-cuprate (TMP)2CuLi in situ prepared from CuCl2*TMEDA through successive addition of 1 equivalent of butyllithium and 2 equivalents of LiTMP. The intermediate lithium (hetero)arylcuprates were evidenced by trapping with iodine, allyl bromide, methyl iodide and benzoyl chlorides, the latter giving the best results. Symmetrical dimers were also prepared from lithium azine and diazine cuprates using nitrobenzene as oxidative agent.
Domaines
Chimie organique
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