Photo-induced Dehalogenative Deuteration and Elimination of Alkyl Halides Enabled by Phosphine-mediated Halogen-atom Transfer

Overview

Journal Chem Sci

Publisher Royal Society of Chemistry

Specialty Chemistry

Date 2025 Mar 10

PMID 40060101

Authors

Wei Shi

Bin Guan

Jian Tian

Chao Yang

Lin Guo

Yating Zhao

Wujiong Xia

Affiliations

Soon will be listed here.

Abstract

Dehalogenative deuteration of organic halides is an efficient and straightforward method for incorporating deuterium atoms at specific locations within target molecules. However, utilizing organic halides in photoredox chemistry, particularly unactivated alkyl halides, presents challenges due to their low reduction potentials. In this work, we present a general and effective photoinduced dehalogenative deuteration method for a diverse array of alkyl halides, employing DO as an economical source of deuterium. The use of CyP as a halogen-atom transfer reagent facilitates the dehalogenation of alkyl halides. This method demonstrates a broad scope, with over 70 examples, and shows excellent tolerance for various alkyl halides. The precise dehalogenation of complex alkyl halides highlights the potential of this protocol for late-stage dehalogenative deuteration of natural product derivatives and pharmaceutical compounds. Additionally, the dehalogenative elimination of unactivated alkyl halides can also be achieved by integrating photoredox and cobalt catalysis using the same halogen-atom transfer agents.

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