Combining Ru-Catalyzed C–H Functionalization with Pd-Catalyzed Asymmetric Allylic Alkylation: Synthesis of 3‑Allyl-3-aryl Oxindole Derivatives from Aryl α‑Diazoamides

Ruthenium-catalyzed C–H functionalization was successfully combined with palladium-catalyzed asymmetric allylic alkylation in one pot. The novel dual-metal-catalyzed reaction provides a variety of 3-allyl-3-aryl oxindoles from the corresponding α-diazoamides in up to 99% yield with up to 85% ee. The...

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Veröffentlicht in:Organic letters 2016-10, Vol.18 (19), p.4954-4957
Hauptverfasser: Yamamoto, Kosuke, Qureshi, Zafar, Tsoung, Jennifer, Pisella, Guillaume, Lautens, Mark
Format: Artikel
Sprache:eng
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Zusammenfassung:Ruthenium-catalyzed C–H functionalization was successfully combined with palladium-catalyzed asymmetric allylic alkylation in one pot. The novel dual-metal-catalyzed reaction provides a variety of 3-allyl-3-aryl oxindoles from the corresponding α-diazoamides in up to 99% yield with up to 85% ee. The appropriate ligand choice is important to promote the sequential reaction, avoiding undesired metal interaction or ligand exchange.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.6b02423