Direct allylic acylation via cross-coupling involving cooperative N‑heterocyclic carbene, hydrogen atom transfer, and photoredox catalysis

Xiaochen Wang, Rongxin Yang, Binbing Zhu, Yuxiu Liu, Hongjian Song, Jianyang Dong and Qingmin Wang ()
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Xiaochen Wang: Nankai University
Rongxin Yang: Nankai University
Binbing Zhu: Nankai University
Yuxiu Liu: Nankai University
Hongjian Song: Nankai University
Jianyang Dong: Nankai University
Qingmin Wang: Nankai University

Nature Communications, 2023, vol. 14, issue 1, 1-10

Abstract: Abstract Herein, we report a mild, operationally simple, multicatalytic method for the synthesis of β,γ-unsaturated ketones via allylic acylation of alkenes. Specifically, the method combines N‑heterocyclic carbene catalysis, hydrogen atom transfer catalysis, and photoredox catalysis for cross-coupling reactions between a wide range of feedstock carboxylic acids and readily available olefins to afford structurally diverse β,γ-unsaturated ketones without olefin transposition. The method could be used to install acyl groups on highly functionalized natural-product-derived compounds with no need for substrate pre-activation, and C–H functionalization proceed with excellent site selectivity. To demonstrate the potential applications of the method, we convert a representative coupling product into various useful olefin synthons.

Date: 2023
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DOI: 10.1038/s41467-023-38743-8

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