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

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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… Click to show full abstract

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.

Keywords: ketones aldehydes; alkylation; catalyzed redox; redox cascade; direct alkylation; alkylation ketones

Journal Title: Journal of the American Chemical Society
Year Published: 2018

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