Enantioselective photoredox dehalogenative protonation

Chemical Science
Meimei HouZhiyong Jiang

Abstract

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.

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Citations

Sep 20, 2019·Organic & Biomolecular Chemistry·Chunhui JiangHongfei Lu
Sep 7, 2019·Chemical Communications : Chem Comm·Xiangyuan LiuZhiyong Jiang
May 28, 2020·Organic & Biomolecular Chemistry·Bor-Cherng Hong
Jan 10, 2020·Chemistry : a European Journal·Beeraiah BaireSanthi Jampani
Sep 4, 2019·Chemical Communications : Chem Comm·Guangkuo ZengZhiyong Jiang
Oct 22, 2020·Beilstein Journal of Organic Chemistry·Callum PrenticeEli Zysman-Colman
Mar 30, 2021·Organic Letters·Zhen-Yao DaiPu-Sheng Wang

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Methods Mentioned

BETA
column chromatography

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