Pd-Catalyzed Sequential Arylation of 7‑Azaindoles: Aggregate-Induced Emission of Tetra-Aryl 7‑Azaindoles

Pd-Catalyzed Sequential Arylation of 7‑Azaindoles: Aggregate-Induced Emission of Tetra-Aryl 7‑Azaindoles

Pd-catalyzed synthesis of multi-aryl 7-azaindoles using sequential arylation of 5-bromo-6-chloro-3-iodo-1-methyl-1H-pyrrolo­[2,3-b] pyridine is established. Four diverse aryl groups are installed in a chemo-selective fashion providing a general method to synthesize sterically encumbered compounds an...

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Veröffentlicht in:Journal of organic chemistry 2019-11, Vol.84 (21), p.14015-14029
Hauptverfasser: Cardoza, Savio, Das, Parthasarathi, Tandon, Vibha
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container_end_page 14029
container_issue 21
container_start_page 14015
container_title Journal of organic chemistry
container_volume 84
creator Cardoza, Savio
Das, Parthasarathi
Tandon, Vibha
description Pd-catalyzed synthesis of multi-aryl 7-azaindoles using sequential arylation of 5-bromo-6-chloro-3-iodo-1-methyl-1H-pyrrolo­[2,3-b] pyridine is established. Four diverse aryl groups are installed in a chemo-selective fashion providing a general method to synthesize sterically encumbered compounds and extended 7-azaindoles in 48–95% yields. Three-selective sequential arylations at C-3, C-5, and C-6 via Suzuki–Miyaura cross-coupling followed by direct C-2 arylation using a Pd catalyst and AgOTf as an additive are highlights of the present work. Interestingly, the tetra-aryl 7-azaindoles showed aggregate-induced emission (AIE) making it potentially useful as fluorophores in OLEDs, sensors, and bio-imaging tools.
doi_str_mv 10.1021/acs.joc.9b02187
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title Pd-Catalyzed Sequential Arylation of 7‑Azaindoles: Aggregate-Induced Emission of Tetra-Aryl 7‑Azaindoles
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