In Situ Anionic Shielding for Regioselective Metalation: Directed peri and Iterative Metalation Routes to Polyfunctionalized 7-Azaindoles - Normandie Université Access content directly
Journal Articles Angewandte Chemie International Edition Year : 2012

In Situ Anionic Shielding for Regioselective Metalation: Directed peri and Iterative Metalation Routes to Polyfunctionalized 7-Azaindoles

Abstract

Strolling the ring: a general regioselective directed peri(C4)-metalation route to 1 through an in situ N-anionic protection of C2 is reported. The azaindoles may be elaborated by directed ortho metalation (DoM) and Suzuki coupling to more complex heterocyclic systems. An iterative ring-walk DoM sequence furnishes the exhaustively substituted 2. DMG=directed metalation group, TMEDA=N,N,N',N'-tetramethylethylenediamine, TMS=trimethylsilyl.

Dates and versions

hal-02380527 , version 1 (26-11-2019)

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Cédric Schneider, Emilie David, Anton Toutov, Victor Snieckus. In Situ Anionic Shielding for Regioselective Metalation: Directed peri and Iterative Metalation Routes to Polyfunctionalized 7-Azaindoles. Angewandte Chemie International Edition, 2012, 51 (11), pp.2722-2726. ⟨10.1002/anie.201108016⟩. ⟨hal-02380527⟩
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