Enantioselective Photoredox Dehalogenative Protonation

Overview

Journal Chem Sci

Publisher Royal Society of Chemistry

Specialty Chemistry

Date 2019 Aug 2

PMID 31367315

Citations 8

Authors

Meimei Hou

Lu Lin

Xiangpei Chai

Xiaowei Zhao

Baokun Qiao

Zhiyong Jiang

Affiliations

Soon will be listed here.

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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