Chan-Evans-Lam Cu(II)-Catalyzed C–O Cross-Couplings: Broadening Synthetic Access to Functionalized Vinylic Ethers

We report a general and effective Cu(OAc)<sub>2</sub>-catalyzed C-O cross-coupling synthesis of di- and trisubstituted vinylic ethers, using a combination of <i>N</i>-isopropylimidazole ligand and dicumyl peroxide as stoichiometric oxidant. This method couples functionalized vinylic pinacolboronates with various 1° and 2° alcohols to provide single-step syntheses of novel and structurally complex vinylic ethers. The optimized conditions do not require excess alcohol reactant and substantially suppress competing side reactions.

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Publication Details

Journal
Organic Letters
Published
2025-06-27
DOI
https://doi.org/10.1021/acs.orglett.5c01966
Citations
1
Primary Topic
Catalytic Cross-Coupling Reactions
Type
article
Field-Weighted Citation Impact
0.94
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article

Chan-Evans-Lam Cu(II)-Catalyzed C–O Cross-Couplings: Broadening Synthetic Access to Functionalized Vinylic Ethers

San L. Pham, Frank E. McDonald
1 citations
Organic Letters
Catalytic Cross-Coupling Reactions
0.94
article

Chan-Evans-Lam Cu(II)-Catalyzed C–O Cross-Couplings: Broadening Synthetic Access to Functionalized Vinylic Ethers

San L. Pham, Frank E. McDonald
article en
1 citations

Abstract

We report a general and effective Cu(OAc)<sub>2</sub>-catalyzed C-O cross-coupling synthesis of di- and trisubstituted vinylic ethers, using a combination of <i>N</i>-isopropylimidazole ligand and dicumyl peroxide as stoichiometric oxidant. This method couples functionalized vinylic pinacolboronates with various 1° and 2° alcohols to provide single-step syntheses of novel and structurally complex vinylic ethers. The optimized conditions do not require excess alcohol reactant and substantially suppress competing side reactions.

Organic LettersVol. 27(27)
Emory University (US)
Openalex Percentile: Top 24%
Catalytic Cross-Coupling Reactions
0.94
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