In situ anionic shielding for regioselective metalation: directed peri and iterative metalation routes to polyfunctionalized 7-azaindoles |
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| Authors: | Schneider Cédric David Emilie Toutov Anton A Snieckus Victor |
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| Affiliation: | Department of Chemistry, Queen's University, Kingston, Ontario, Canada. |
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| 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. |
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| Keywords: | heterocycles metalation regioselectivity structure elucidation synthetic methods |
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