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

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

  • Org Biomol Chem. 2022 Feb 9;20(6):1176-1180. doi: 10.1039/d1ob02285g.
Fei-Fei Sheng 1,  En-Ci Li 1,  Jing-Wen Bai 1,  Cai-Xia Wang 1,  Guang-Qi Hu 1,  Kai-Hui Liu 1,  Zheng-Yi Sun 1,  Kang Shen 1,  Hong-Hai Zhang 1 2
Affiliations

Affiliations

  • 1 Key Laboratory of Flexible Electronics (KLOFE) & Institute of Advanced Materials (IAM), Jiangsu National Synergistic Innovation Center for Advanced Materials (SICAM), Nanjing Tech. University (Nanjing Tech.), 30 Puzhu Road, Nanjing 211816, P. R. China. iamhhzhang@njtech.edu.cn.
  • 2 Neutron Scattering Division & Center for Nanophase Materials Sciences, Oak Ridge National Laboratory, Oak Ridge, Tennessee 37830, USA. zhangh1@ornl.gov.
PMID: 35044395 DOI: 10.1039/d1ob02285g
Abstract

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.

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