Lithium cadmate-mediated deprotonative metalation of anisole: experimental and computational study

Katia Snégaroff (1) , Shinsuke Komagawa (2) , M. Yonehara (3) , Floris Chevallier (1) , Philippe C. Gros (4) , Masanobu Uchiyama (2) , Florence Mongin (5)

1 CPM - Chimie et Photonique Moléculaires
2 RIKEN CBS - RIKEN Center for Brain Science [Wako]
3 RIKEN - RIKEN - Institute of Physical and Chemical Research [Japon]
4 SRSMC - Structure et Réactivité des Systèmes Moléculaires Complexes
5 ISCR - Institut des Sciences Chimiques de Rennes

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

Domaines: Chimie organique

Katia Snégaroff, Shinsuke Komagawa, M. Yonehara, Floris Chevallier, Philippe C. Gros, et al.. Lithium cadmate-mediated deprotonative metalation of anisole: experimental and computational study. Journal of Organic Chemistry, 2010, 75 (9), pp.3117-3120. ⟨10.1021/jo100150S⟩. ⟨hal-00785078⟩