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]

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

Domains: Chemical Sciences; Chemical Sciences; Organic chemistry; Chemical Sciences; Catalysis

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⟩