Lithium Cadmate-Mediated Deprotonative Metalation of Anisole: Experimental and Computational Study
The Journal of Organic Chemistry2010Vol. 75(9), pp. 3117–3120
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K. Snegaroff, Shinsuke Komagawa, Mitsuhiro Yonehara, Floris Chevallier, Philippe C. Gros, Masanobu Uchiyama, Florence Mongin
Abstract
Lithium cadmates bearing different ligands were compared with efficient (TMP)(3)CdLi (TMP = 2,2,6,6-tetramethylpiperidino) for their ability to deprotometalate anisole. The generated arylcadmates were evidenced using I(2). The results show that it is possible to replace only one of the TMP (with a piperidino, a diisopropylamino, a butyl, or a sec-butyl) without important yield drop. In the light of DFT calculations, reaction pathways were proposed for the deprotocadmations of anisole using a triamino, an alkyldiamino, and an aminodialkyl cadmate.
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