Direct β‑Alkylation of Ketones and Aldehydes via Pd-Catalyzed Redox Cascade

We report a direct β-alkylation of ketones and aldehydes with simple alkyl bromides through a Pd-catalyzed redox-cascade strategy. The use of a Cu cocatalyst is important for improved efficiency. The reaction is redox-neutral, without the need for strong acids or bases. Both cyclic and acyclic keton...

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Veröffentlicht in:Journal of the American Chemical Society 2018-05, Vol.140 (19), p.6057-6061
Hauptverfasser: Wang, Chengpeng, Dong, Guangbin
Format: Artikel
Sprache:eng
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Zusammenfassung:We report a direct β-alkylation of ketones and aldehydes with simple alkyl bromides through a Pd-catalyzed redox-cascade strategy. The use of a Cu cocatalyst is important for improved efficiency. The reaction is redox-neutral, without the need for strong acids or bases. Both cyclic and acyclic ketones, as well as α-branched aldehydes, are suitable substrates for coupling with secondary and tertiary alkyl bromides. Concise formal synthesis of Zanapezil is achieved using this β-alkylation method.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.8b03530