4.8 Article

Synthesis of Deuterated (E)-Alkene through Xanthate-Mediated Hydrogen-Deuterium Exchange Reactions

Journal

ORGANIC LETTERS
Volume 23, Issue 19, Pages 7412-7417

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c02600

Keywords

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Funding

  1. Foundation of the Department of Education of Guangdong Province [2018KZDXM070, 2019KZDXM052, 2021KTSCX140]
  2. Science Foundation for Young Teachers of Wuyi University [2019td06]
  3. College Students Innovation and Entrepreneurship Training Program [S2020211349091, 2019cx01, 2020cx26]

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This study developed a reversible hydrogen-deuterium exchange reaction for nonactivated olefins, achieving reversible exchange between ordinary olefins and deuterated olefins. By using the lowest cost D2O without precious metal catalysts and ligands, a broad spectrum of functional groups compatibility was achieved.
Herein we have developed a reversible hydrogen-deuterium exchange reaction of nonactivated olefins. By using EtOCS2K as a mediator, the H/D exchange reaction was realized through repeated addition and elimination reactions, demonstrating reversible H/D exchange between ordinary olefins and deuterated olefins. Using the lowest cost D2O without precious metal catalysts and ligands, a broad spectrum of compatibility of functional groups was achieved.

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