Citation: Zhen Liu, Zhi-Yuan Ren, Chen Yang, Xiangyi Shao, Li Chen, Xin Li. Asymmetric alkenylation reaction of benzoxazinones with diarylethylenes catalyzed by B(C₆F₅)₃/chiral phosphoric acid[J]. Chinese Chemical Letters, ;2024, 35(5): 108939. doi: 10.1016/j.cclet.2023.108939 shu

Asymmetric alkenylation reaction of benzoxazinones with diarylethylenes catalyzed by B(C₆F₅)₃/chiral phosphoric acid

Zhen Liu ^a ,
Zhi-Yuan Ren ^a ,
Chen Yang ^a ,
Xiangyi Shao ^{a, c} ,
Li Chen ^{a, b, *,} ,
Xin Li ^{a, b, *,}

a.
State Key Laboratory of Elemento-Organic Chemistry, Frontiers Science Center for New Organic Matter, College of Chemistry, Nankai University, Tianjin 300071, China
b.
Haihe Laboratory of Sustainable Chemical Transformations, Tianjin 300192, China
c.
Zhenhai High School of Zhejiang, Ningbo 315299, China

chenliss@nankai.edu.cn

xin_li@nankai.edu.cn

Received Date: 28 May 2023
Revised Date: 3 August 2023
Accepted Date: 17 August 2023
Available Online: 19 August 2023

Figures(6)

Catalytic enantioselective alkenylation is an efficient method to construct chiral alkene molecules, but the asymmetric alkenylation of simple alkenes catalyzed by metal-free catalysts remains an elusive challenge. Herein, we reported an asymmetric alkenylation of benzoxazinones with diarylethylenes by utilizing a B(C₆F₅)₃/chiral phosphoric acid catalyst. A broad of benzoxazinones and diarylethylenes with electron-withdrawing and electron-donating groups were tolerated (up to 95% yield and 97.5:2.5 e.r.) in the methodology under mild reaction conditions. Moreover, the synthetic utility was confirmed by the scaled-up reaction and transformations of the products. The mechanism was preliminarily explored by control reactions, nonlinear effect experiment and DFT calculations.
- Asymmetric alkenylation,
- Simple alkenes,
- Benzoxazinones,
- B(C₆F₅)₃/chiral phosphoric acid,
- Theoretical calculations
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沈阳化工大学材料科学与工程学院沈阳 110142

Asymmetric alkenylation reaction of benzoxazinones with diarylethylenes catalyzed by B(C6F5)3/chiral phosphoric acid

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通讯作者: 陈斌, bchen63@163.com

Asymmetric alkenylation reaction of benzoxazinones with diarylethylenes catalyzed by B(C₆F₅)₃/chiral phosphoric acid