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

Cédric Schneider 1 Emilie David 1 Anton Toutov 2 Victor Snieckus 2
1 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse
2 Queen's University [Kingston, Canada]
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.
Keywords : heterocycles metalation regioselectivity structure elucidation synthetic methods
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Journal articles
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https://hal-normandie-univ.archives-ouvertes.fr/hal-02380527
Contributor : Cédric Schneider <>
Submitted on : Tuesday, November 26, 2019 - 11:59:56 AM
Last modification on : Monday, December 7, 2020 - 9:44:02 AM

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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, Wiley-VCH Verlag, 2012, 51 (11), pp.2722-2726. ⟨10.1002/anie.201108016⟩. ⟨hal-02380527⟩

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