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Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Ni-Catalyzed (A + 2B)-Type Reductive Coupling of Electron-Deficient Alkenes and Alkynes through a Selective
Ming-Bai Gou1, Deng-Yin Gou1, Chun-Min Yang1
1State Key Laboratory of Discovery and Utilization of Functional Components in Traditional Chinese Medicine & School of Pharmaceutical Sciences, Guizhou Medical University, 561113 Guiyang, P. R. China.
Abstract:
The first nickel-catalyzed (A + 2B)-type reductive coupling of electron-deficient alkenes with alkynes has been developed. This method provides efficient access to diverse α-skipped dienyl esters in up to 99% yield with high chemo- and stereoselectivity. Synthetic utility is demonstrated in the late-stage modification of bioactive molecules and the development of antibacterial agents. Mechanistic studies indicate a stepwise pathway involving selective trimerization of alkenes with alkynes followed by a nickelacycle-mediated formal 1,6-reduction.
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