4.4 Article

New Gilman-type lithium cuprate from a copper(II) salt: synthesis and deprotonative cupration of aromatics

期刊

TETRAHEDRON LETTERS
卷 50, 期 49, 页码 6787-6790

出版社

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2009.09.100

关键词

Lithium; Copper; Metalation; Aromatic compound; Heterocycle

资金

  1. MESR of France

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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)(2)CuLi in situ prepared from CuCl2. TMEDA through successive addition of 1 equiv of butyllithium and 2 equiv 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 an oxidative agent. (C) 2009 Elsevier Ltd. All rights reserved.

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