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

TETRAHEDRON LETTERS

卷:50

Article

Nguyen, Tan Tai¹  Chevallier, Floris¹  Jouikov, Viatcheslav¹  Mongin, Florence¹ 

[1] Univ Rennes 1, UMR CNRS 6510, F-35042 Rennes, France

关键词: Lithium;    Copper;    Metalation;    Aromatic compound;    Heterocycle;   

DOI  :  10.1016/j.tetlet.2009.09.100

来源: Elsevier

【 摘 要 】

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.

【 授权许可】

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