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. 2022 Jul 22:10:962355.
doi: 10.3389/fchem.2022.962355. eCollection 2022.

Palladium-catalyzed allylic etherification of phenols with vinyl ethylene carbonate

Shibo Lin  1 , Xiaotian Zhao  1 , Lihui He  1 , Xuanhao Li  1 , Qian Jiang  1 , Lan Xiang  1 , Yongqin Ye  1 , Xiaohong Gan  1
Affiliations

Palladium-catalyzed allylic etherification of phenols with vinyl ethylene carbonate

Shibo Lin et al. Front Chem. .

Abstract

The palladium-catalyzed decarboxylative reactions of phenols and vinyl ethylene carbonate to produce allylic aryl ethers under mild conditions have been established. Adopting an inexpensive PdCl2(dppf) catalyst promotes the efficient conversion of phenols to the corresponding allylic aryl ethers via the formation of a new C-O bond in good isolated yields with complete regioselectivities, acceptable functional group tolerance and operational simplicity. The robust procedure could be completed smoothly by conducting a scaled-up reaction with comparable efficiency to afford the target product.

Keywords: C-O bond formation; allylic etherification; palladium-catalyzed; phenols; vinyl ethylene carbonate.

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Conflict of interest statement

The authors declare that the research was conducted in the absence of any commercial or financial relationships that could be construed as a potential conflict of interest.

Figures

FIGURE 1
FIGURE 1
Representative important molecules containing aryl ether fragments.
FIGURE 2
FIGURE 2
Strategy for Pd-catalyzed decarboxylative reactions of VEC with phenols.
FIGURE 3
FIGURE 3
Substrate Scope of phenols. Reaction conditions: Phenol 1 (0.20 mmol), 2 (0.30 mmol), PdCl2(dppf) (5 mol%), Cs2CO3 (0.06 mmol), MeCN (2 ml), 70°C, 15 h. Isolated yields are reported.
FIGURE 4
FIGURE 4
Competition experiments between 1h and 1k.
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