Enantioselective photoredox dehalogenative protonation

Meimei Hou; Lu Lin; Xiangpei Chai; Xiaowei Zhao; Baokun Qiao; Zhiyong Jiang

doi:10.1039/C9SC02000D

Enantioselective photoredox dehalogenative protonation†

Meimei Hou,‡^a Lu Lin,‡^a Xiangpei Chai,‡^a Xiaowei Zhao,^a Baokun Qiao*^a and Zhiyong Jiang

*^ab

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* Corresponding authors

^a Henan University, Jinming Campus, Kaifeng, Henan 475004, China
E-mail: jiangzhiyong@htu.edu.cn, chmjzy@henu.edu.cn

^b Henan Key Laboratory of Organic Functional Molecules and Drug Innovation, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007, China

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.

This article is part of the themed collection: 2019 Chemical Science HOT Article Collection

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DOI: https://doi.org/10.1039/C9SC02000D
Article type: Edge Article
Submitted: 23 Apr 2019
Accepted: 29 May 2019
First published: 07 Jun 2019
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry

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Chem. Sci., 2019,10, 6629-6634

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Enantioselective photoredox dehalogenative protonation

M. Hou, L. Lin, X. Chai, X. Zhao, B. Qiao and Z. Jiang, Chem. Sci., 2019, 10, 6629 DOI: 10.1039/C9SC02000D

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

Chemical Science

Enantioselective photoredox dehalogenative protonation†

Abstract

Supplementary files

Article information

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Enantioselective photoredox dehalogenative protonation

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