中国化学快报(英文版)2024,Vol.35Issue(5) :135-140.DOI:10.1016/j.cclet.2023.108939

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

Zhen Liu Zhi-Yuan Ren Chen Yang Xiangyi Shao Li Chen Xin Li
中国化学快报(英文版)2024,Vol.35Issue(5) :135-140.DOI:10.1016/j.cclet.2023.108939

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

Zhen Liu 1Zhi-Yuan Ren 1Chen Yang 1Xiangyi Shao 2Li Chen 3Xin Li3
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作者信息

  • 1. State Key Laboratory of Elemento-Organic Chemistry,Frontiers Science Center for New Organic Matter,College of Chemistry,Nankai University,Tianjin 300071,China
  • 2. State Key Laboratory of Elemento-Organic Chemistry,Frontiers Science Center for New Organic Matter,College of Chemistry,Nankai University,Tianjin 300071,China;Zhenhai High School of Zhejiang,Ningbo 315299,China
  • 3. State Key Laboratory of Elemento-Organic Chemistry,Frontiers Science Center for New Organic Matter,College of Chemistry,Nankai University,Tianjin 300071,China;Haihe Laboratory of Sustainable Chemical Transformations,Tianjin 300192,China
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Abstract

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 chal-lenge.Herein,we reported an asymmetric alkenylation of benzoxazinones with diarylethylenes by uti-lizing 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.

Key words

Asymmetric alkenylation/Simple alkenes/Benzoxazinones/B(C6F5)3/chiral phosphoric acid/Theoretical calculations

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基金项目

国家自然科学基金(22193011)

国家自然科学基金(21971120)

国家自然科学基金(21933008)

National Science and Technology Fundamental Resource Investigation Program of China(2018FY201200)

出版年

2024
中国化学快报(英文版)
中国化学会

中国化学快报(英文版)

CSTPCD
影响因子:0.771
ISSN:1001-8417
参考文献量60
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