Ni-Catalyzed Suzuki-Miyaura Cross-Coupling of α-Oxo-vinylsulfones To Prepare C-Aryl Glycals and Acyclic Vinyl Ethers

Liang Gong; Hong-Bao Sun; Li-Fan Deng; Xia Zhang; Jie Liu; Shengyong Yang; Dawen Niu

doi:10.1021/jacs.9b02312

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Ni-Catalyzed Suzuki-Miyaura Cross-Coupling of α-Oxo-vinylsulfones To Prepare C-Aryl Glycals and Acyclic Vinyl Ethers

Liang Gong, Hong-Bao Sun, Li-Fan Deng, Xia Zhang, Jie Liu, Shengyong Yang and Dawen Niu

Journal of the American Chemical Society, Vol.141(19), pp.7680-7686

05/15/2019

DOI: https://doi.org/10.1021/jacs.9b02312

PMID: 31025860

Abstract

Ethers

Electrophiles

Vinyl

Sulfones

Cross coupling reaction

We demonstrate that readily available and bench-stable α-oxo-vinylsulfones are competent electrophiles in Ni-catalyzed Suzuki-Miyaura cross-coupling reactions. The C-sulfone bond in the α-oxo-vinylsulfone motif is cleaved chemoselectively in these reactions, furnishing C-aryl glycals or acyclic vinyl ethers in high yields. These reactions proceed under mild conditions and tolerate a remarkable scope of heterocycles and functional groups. Preliminary mechanistic studies revealed the importance of an α-heteroatom in facilitating these transformations.

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Title: Ni-Catalyzed Suzuki-Miyaura Cross-Coupling of α-Oxo-vinylsulfones To Prepare C-Aryl Glycals and Acyclic Vinyl Ethers
Creators: Liang Gong - Department of Emergency, State Key Laboratory of Biotherapy and Cancer Center, West China Hospital, and School of Chemical Engineering , Sichuan University , Chengdu 610041 , China
Hong-Bao Sun - Department of Emergency, State Key Laboratory of Biotherapy and Cancer Center, West China Hospital, and School of Chemical Engineering , Sichuan University , Chengdu 610041 , China
Li-Fan Deng - Department of Emergency, State Key Laboratory of Biotherapy and Cancer Center, West China Hospital, and School of Chemical Engineering , Sichuan University , Chengdu 610041 , China
Xia Zhang - Department of Emergency, State Key Laboratory of Biotherapy and Cancer Center, West China Hospital, and School of Chemical Engineering , Sichuan University , Chengdu 610041 , China
Jie Liu - Department of Emergency, State Key Laboratory of Biotherapy and Cancer Center, West China Hospital, and School of Chemical Engineering , Sichuan University , Chengdu 610041 , China
Shengyong Yang - Department of Emergency, State Key Laboratory of Biotherapy and Cancer Center, West China Hospital, and School of Chemical Engineering , Sichuan University , Chengdu 610041 , China
Dawen Niu - Department of Emergency, State Key Laboratory of Biotherapy and Cancer Center, West China Hospital, and School of Chemical Engineering , Sichuan University , Chengdu 610041 , China
Publication Details: Journal of the American Chemical Society, Vol.141(19), pp.7680-7686
Publisher: United States
Identifiers: 9923972852601921
Academic Unit: Department of Chemistry
Language: English
Resource Type: Journal article

Ni-Catalyzed Suzuki-Miyaura Cross-Coupling of α-Oxo-vinylsulfones To Prepare C-Aryl Glycals and Acyclic Vinyl Ethers

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