Direct Enol Ether Metalation–Negishi Coupling Strategy To Prepare α-Heteroaryl Enol Ethers

Peng, Feng; Liu, Kailin; Zhang, Huangguang; Xu, Fuchun; Liu, Yanan; Shang, Gao

doi:10.1021/acs.orglett.3c03517

Org. Lett.

2023

DOI: 10.1021/acs.orglett.3c03517

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Direct Enol Ether Metalation–Negishi Coupling Strategy To Prepare α-Heteroaryl Enol Ethers

Feng Peng,

Kailin Liu,

Huangguang Zhang

et al.

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2024

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Cited by 2 publications

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Modular Synthesis of Fully‐Substituted and Configuration‐Defined Alkyl Vinyl Ethers Enabled by Dual‐Functional Copper Catalysis

Jiang,

Chen,

Xia

2024

Angewandte Chemie

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Here we present a modular, chemo‐, regio‐, and stereoselective synthesis of fully‐substituted and configuration‐defined alkyl vinyl ethers (AVEs) using simple chemical feedstocks. The distinctive approach involves the chemo‐ and regioselective functionalization of the CF2 unit in gem‐difluorinated cyclopropanes with O‐H and C‐H nucleophiles in a specific order. The resulting highly functionalized cyclopropanyl ethers then undergo a stereoselective ring‐opening process to produce fully‐substituted and configuration‐defined AVEs. These AVEs are rarely accessible through conventional methods and are easily transformable. Mechanistic experiments indicate that the success of this method relies on the use of dual‐functional copper catalysis, which is involved in both the functionalization of the CF2 unit and the subsequent ring‐opening process.

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Modular Synthesis of Fully‐Substituted and Configuration‐Defined Alkyl Vinyl Ethers Enabled by Dual‐Functional Copper Catalysis

Jiang,

Chen,

Xia

2024

Angewandte Chemie

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show abstract

Modular Synthesis of Fully‐Substituted and Configuration‐Defined Alkyl Vinyl Ethers Enabled by Dual‐Functional Copper Catalysis

Jiang,

Chen,

Xia

2024

Angew Chem Int Ed

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Direct Enol Ether Metalation–Negishi Coupling Strategy To Prepare α-Heteroaryl Enol Ethers

Cited by 2 publications

References 25 publications

Modular Synthesis of Fully‐Substituted and Configuration‐Defined Alkyl Vinyl Ethers Enabled by Dual‐Functional Copper Catalysis

Modular Synthesis of Fully‐Substituted and Configuration‐Defined Alkyl Vinyl Ethers Enabled by Dual‐Functional Copper Catalysis

Modular Synthesis of Fully‐Substituted and Configuration‐Defined Alkyl Vinyl Ethers Enabled by Dual‐Functional Copper Catalysis

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