Lithium Cadmate-Mediated Deprotonative Metalation of Anisole: Experimental and Computational Study | Zendy

K. Snegaroff | Zendy; Shinsuke Komagawa | Zendy; Mitsuhiro Yonehara | Zendy; Floris Chevallier | Zendy; Philippe C. Gros | Zendy; Masanobu Uchiyama | Zendy; Florence Mongin | Zendy

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Lithium Cadmate-Mediated Deprotonative Metalation of Anisole: Experimental and Computational Study

Author(s) -

K. Snegaroff,

Shinsuke Komagawa,

Mitsuhiro Yonehara,

Floris Chevallier,

Philippe C. Gros,

Masanobu Uchiyama,

Florence Mongin

Publication year - 2010

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/jo100150s

Subject(s) - anisole , metalation , lithium (medication) , chemistry , yield (engineering) , computational chemistry , medicinal chemistry , organic chemistry , materials science , catalysis , psychology , psychiatry , metallurgy

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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