Silver salt enabled H/D exchange at the β-position of thiophene rings: synthesis of fully deuterated thiophene derivatives

We disclose a silver catalyzed H/D exchange reaction, which can introduce the deuterium atom at the β position of thiophene rings without the assistance of any coordinating groups. The advantages of this reaction include operation in open air, usage of D O as the deuterium source, good tolerance to...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2022-02, Vol.20 (6), p.1176-1180
Main Authors: Sheng, Fei-Fei, Li, En-Ci, Bai, Jing-Wen, Wang, Cai-Xia, Hu, Guang-Qi, Liu, Kai-Hui, Sun, Zheng-Yi, Shen, Kang, Zhang, Hong-Hai
Format: Article
Language:English
Subjects:
Deuteration
Deuterium
Exchanging
Functional groups
Hydrogen-deuterium exchange
Silver
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Summary:We disclose a silver catalyzed H/D exchange reaction, which can introduce the deuterium atom at the β position of thiophene rings without the assistance of any coordinating groups. The advantages of this reaction include operation in open air, usage of D O as the deuterium source, good tolerance to a range of functional groups and obtaining high atom% deuterium incorporation. In addition, this H/D exchange reaction is employed for direct deuteration of a thiophene based monomer, which is usually prepared by multistep synthesis from expensive deuterated starting materials.
ISSN:1477-0520
1477-0539
DOI:10.1039/d1ob02285g