Migratory allylic arylation of 1,n-enols enabled by nickel catalysis

Dan Zhao, Bing Xu and Can Zhu ()
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Dan Zhao: Fudan University
Bing Xu: Fudan University
Can Zhu: Fudan University

Nature Communications, 2023, vol. 14, issue 1, 1-8

Abstract: Abstract Transition-metal-catalyzed allylic substitution reactions (Tsuji−Trost reactions) proceeding via a π-allyl metal intermediate have been demonstrated as a powerful tool in synthetic chemistry. Herein, we disclose an unprecedented π-allyl metal species migration, walking on the carbon chain involving 1,4-hydride shift as confirmed by deuterium labeling experiments. This migratory allylic arylation can be realized under dual catalysis of nickel and lanthanide triflate, a Lewis acid. Olefin migration has been observed to preferentially occur with the substrate of 1,n-enols (n ≥ 3). The robust nature of the allylic substitution strategy is reflected by a broad scope of substrates with the control of regio- and stereoselectivity. DFT studies suggest that π-allyl metal species migration consists of the sequential β-H elimination and migratory insertion, with diene not being allowed to release from the metal center before producing a new π-allyl nickel species.

Date: 2023
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DOI: 10.1038/s41467-023-38865-z

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