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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Lithium cadmate-mediated deprotonative metalation of anisole: experimental and computational study.
J Org Chem
May 2010
Chimie et Photonique Moléculaires, UMR 6510 CNRS, Université de Rennes 1, Bâtiment 10A, Case 1003, Campus Scientifique de Beaulieu, 35042 Rennes, France.
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.
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