P-Spiro phosphonium salts catalyzed asymmetric fluorination of 3-substituted benzofuran-2(3H)-ones

By using chiral phosphonium salts as phase-transfer catalysts, a series of fluorinated benzofuran-2(3H)-ones were obtained with up to 96% yield and 56% ee. •An asymmetric electrophilic fluorination of 3-substituted benzofuran-2(3H)-ones is described.•Chiral phosphonium salts were used as phase-trans...

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Bibliographic Details
Published in:Journal of fluorine chemistry 2013-06, Vol.150, p.60-66
Main Authors: Zhu, Chuan-Le, Fu, Xiao-Yun, Wei, Ai-Jia, Cahard, Dominique, Ma, Jun-An
Format: Article
Language:English
Subjects:
Benzofuran-2(3H)-ones
Chemical Sciences
Enantioselectivity
Fluorination
Organic chemistry
Phase-transfer catalysis
Phosphonium salts
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Summary:By using chiral phosphonium salts as phase-transfer catalysts, a series of fluorinated benzofuran-2(3H)-ones were obtained with up to 96% yield and 56% ee. •An asymmetric electrophilic fluorination of 3-substituted benzofuran-2(3H)-ones is described.•Chiral phosphonium salts were used as phase-transfer catalysts.•The fluorinated products were obtained in up to 96% yield and 56% ee. Asymmetric electrophilic fluorination of 3-substituted benzofuran-2(3H)-ones was realized under liquid–liquid phase-transfer catalysis with 2mol% of chiral phosphonium salts to afford the fluorinated products with up to 96% yield and 56% ee.
ISSN:0022-1139
1873-3328
DOI:10.1016/j.jfluchem.2013.03.007