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

نویسندگان

  • Katia Snégaroff
  • Shinsuke Komagawa
  • Mitsuhiro Yonehara
  • Floris Chevallier
  • Philippe C Gros
  • Masanobu Uchiyama
  • Florence Mongin
چکیده

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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عنوان ژورنال:
  • The Journal of organic chemistry

دوره 75 9  شماره 

صفحات  -

تاریخ انتشار 2010