4.8 Article

Photoinduced and Palladium-Catalyzed Remote Desaturation of Amide Derivatives

Journal

ORGANIC LETTERS
Volume 23, Issue 17, Pages 6931-6935

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c02509

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Funding

  1. National Natural Science Foundation of China [21971110, 21732003]

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The photoinduced and palladium-catalyzed remote desaturation of O-acyl hydroxamides to unsaturated amides under mild conditions has been achieved efficiently and selectively. This method features good site-selectivity, is terminal oxidant-free, and produces moderate to excellent yields for a variety of unsaturated amides, enabling late-stage desaturation of complex and biologically important molecules.
A photoinduced and palladium-catalyzed remote desaturation of O-acyl hydroxamides to unsaturated amides under mild conditions has been achieved. The formation of the alkyl Pd(II) intermediate by the recombination of alkyl radical and Pd(I) species is critical to achieve this efficient and selective desaturation of alkanes. This reaction features good site-selectivity, is terminal oxidant-free, and produces moderate to excellent yields for a variety of unsaturated amides. Remarkably, this approach enables late-stage desaturation of complex and biologically important molecules.

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