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

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

doi:10.1039/d1ob02285g

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

Journal Article · Fri Dec 24 00:00:00 EST 2021 · Organic and Biomolecular Chemistry

DOI:https://doi.org/10.1039/d1ob02285g· OSTI ID:1866689

Sheng, Fei-Fei ^[1]; Li, En-Ci ^[1]; Bai, Jing-Wen ^[1]; Wang, Cai-Xia ^[1]; Hu, Guang-Qi ^[1]; Liu, Kai-Hui ^[1]; ^[1]; Shen, Kang ^[1]; ^[2]

Nanjing Technical Univ., (China)
Nanjing Technical Univ., (China); Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)

Here, 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 D₂O 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.

View Accepted Manuscript (DOE)

Research Organization:: Oak Ridge National Laboratory (ORNL), Oak Ridge, TN (United States)

Sponsoring Organization:: USDOE; USDOE Office of Science (SC)

Grant/Contract Number:: AC05-00OR22725

OSTI ID:: 1866689

Alternate ID(s):: OSTI ID: 1841038

Journal Information:: Organic and Biomolecular Chemistry, Journal Name: Organic and Biomolecular Chemistry Journal Issue: 6 Vol. 20; ISSN 1477-0520

Publisher:: Royal Society of ChemistryCopyright Statement

Country of Publication:: United States

Language:: English

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