Enantioselective photoredox dehalogenative protonation

We report an enantioselective photoredox dehalogenative protonation as a new type of asymmetric protonation. As a paradigm, with a cooperative catalytic system consisting of a chiral H-bonding catalyst and a dicyanopyrazine-derived chromophore (DPZ) photosensitizer that is irradiated with visible li...

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Bibliographic Details
Published in:Chemical science (Cambridge) 2019-07, Vol.1 (27), p.6629-6634
Main Authors: Hou, Meimei, Lin, Lu, Chai, Xiangpei, Zhao, Xiaowei, Qiao, Baokun, Jiang, Zhiyong
Format: Article
Language:English
Subjects:
Carbonyls
Catalysis
Chromophores
Crystallography
Enantiomers
Halides
Ketones
Protonation
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Summary:We report an enantioselective photoredox dehalogenative protonation as a new type of asymmetric protonation. As a paradigm, with a cooperative catalytic system consisting of a chiral H-bonding catalyst and a dicyanopyrazine-derived chromophore (DPZ) photosensitizer that is irradiated with visible light, a range of cyclic and acyclic ketones with labile chiral secondary C-F, C-Cl and C-Br bonds at the α-position were obtained in high yields with good to excellent enantioselectivities (up to >99% ee) by using a secondary amine as the terminal reductant. Given the ready accessibility of halides, the success of this work should provide inspiration for constructing diverse chiral α-tertiary carbonyls and their variants. We report an enantioselective photoredox dehalogenative protonation as a new type of asymmetric protonation.
ISSN:2041-6520
2041-6539
DOI:10.1039/c9sc02000d