Nickel-catalyzed allylic carbonylative coupling of alkyl zinc reagents with tert-butyl isocyanide

Yangyang Weng, Chenhuan Zhang, Zaiquan Tang, Mohini Shrestha, Wenyi Huang, Jingping Qu () and Yifeng Chen ()
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Yangyang Weng: East China University of Science and Technology
Chenhuan Zhang: East China University of Science and Technology
Zaiquan Tang: East China University of Science and Technology
Mohini Shrestha: East China University of Science and Technology
Wenyi Huang: East China University of Science and Technology
Jingping Qu: East China University of Science and Technology
Yifeng Chen: East China University of Science and Technology

Nature Communications, 2020, vol. 11, issue 1, 1-9

Abstract: Abstract Transition metal-catalyzed carbonylation with carbon nucleophiles is one of the most prominent methods to construct ketones, which are highly versatile motifs prevalent in a variety of organic compounds. In comparison to the well-established palladium catalytic system, the nickel-catalyzed carbonylative coupling is much underdeveloped due to the strong binding affinity of CO to nickel. By leveraging easily accessible tert-butyl isocyanide as the CO surrogate, we present a nickel-catalyzed allylic carbonylative coupling with alkyl zinc reagent, allowing for the practical and straightforward preparation of synthetically important β,γ-unsaturated ketones in a linear-selective fashion with excellent trans-selectivity under mild conditions. Moreover, the undesired polycarbonylation process which is often encountered in palladium chemistry could be completely suppressed. This nickel-based method features excellent functional group tolerance, even including the active aryl iodide functionality to allow the orthogonal derivatization of β,γ-unsaturated ketones. Preliminary mechanistic studies suggest that the reaction proceeds via a π-allylnickel intermediate.

Date: 2020
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DOI: 10.1038/s41467-020-14320-1

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