Selective monodeuteration enabled by bisphosphonium catalyzed ring opening processes-Reference-Cited by-同舟云学术

Selective monodeuteration enabled by bisphosphonium catalyzed ring opening processes

Published:2024-03-04 Issue: Volume: Page:
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Author:

Zuo Zhiwei¹^ORCID,Xu Yuanli²,Chen Wenlong³,Pu Ruihua⁴,Ding Jia³^ORCID,An Qing³,Yang Yi⁵,Liu Weimin⁶^ORCID

Affiliation:

1. State Key Laboratory of Organometallic Chemistry

2. Innovation Center for Chenguang High Performance Fluorine Material, Key Laboratory of Green Chemistry of Sichuan Institutes of Higher Education, Sichuan University of Science and Engineering

3. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences

4. School of Physical Science and Technology, ShanghaiTech University

5. Innovation Center for Chenguang High Performance Fluorine Material, Key Laboratory of Green Chemistry of Sichuan Institutes of Higher Education, Sichuan University of Science and Engineering,

6. ShanghaiTech University

Abstract

Abstract The selective incorporation of a deuterium atom into small molecules with high selectivity is highly valuable for medical and chemical research. Unfortunately, this remains challenging due to the complete deuteration caused by commonly used hydrogen isotope exchange strategies. We report the development of a photocatalytic selective monodeuteration protocol utilizing C–C bond as the unconventional functional handle. The synergistic combination of radical-mediated C–C bond scission and deuterium atom transfer processes has enabled the effective constructions of benzylic CDH moieties with high selectivity for monodeuteration. The combinational use of a bisphosphonium photocatalyst, thiol catalyst, and CH3OD deuteration agent has provided operationally simple conditions for photocatalytic monodeuteration. Moreover, the photoinduced electron transfer process of the bisphosphonium photocatalyst has been elucidated through a series of spectroscopy experiments, identifying a peculiar back electron transfer process that can be regulated by subsequent nucleophilic additions.

Publisher

Research Square Platform LLC

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