期刊论文详细信息
TETRAHEDRON 卷:66
Deprotonative metalation of substituted aromatics using mixed lithium-cobalt combinations
Article
Dayaker, Gandrath1  Chevallier, Floris1  Gros, Philippe C.2  Mongin, Florence1 
[1] Univ Rennes 1, CNRS, UMR 6510, F-35042 Rennes, France
[2] Nancy Univ, CNRS, SRSMC, SOR, F-54506 Vandoeuvre Les Nancy, France
关键词: Bimetallic bases;    Deprotonative metalation;    Aromatic compounds;    Lithium;    Cobalt;   
DOI  :  10.1016/j.tet.2010.09.053
来源: Elsevier
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【 摘 要 】

The deprotonation of anisole was attempted using different homo- and heteroleptic TMP/Bu mixed lithium-cobalt combinations. Using iodine to intercept the metalated anisole, an optimization of the reaction conditions showed that in THF at room temperature 2 equiv of base were required to suppress the formation of the corresponding 2,2'-dimer. The origin of the dimer was not identified, but its formation was favored with allyl bromide as electrophile. The metalated anisole was efficiently trapped using iodine, anisaldehyde, and chlorodiphenylphosphine, and moderately employing benzophenone, and benzoyl chloride. 1,2-, 1,3-, and 1,4-dimethoxybenzene were similarly converted regioselectively to the corresponding iodides. It was observed that 2-methoxy- and 2,6-dimethoxypyridine were more prone to dimerization than the corresponding benzenes when treated similarly. Involving ethyl benzoate in the metalation-iodination sequence showed that the method was not suitable to functionalize substrates bearing reactive functions. (C) 2010 Elsevier Ltd. All rights reserved.

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