<p>Deuterium labeling has found extensive applications across various research fields, including organic synthesis, drug design, and molecular imaging. Electrocatalytic semi-hydrogenation of alkynes offers a viable route for the synthesis of <i>Z</i>-alkenes, yet it falls short in achieving the semi-deuteration of these compounds. In this study, we report an electrochemical cobalt-catalyzed transfer deuteration reaction that proficiently accomplishes the semi-deuteration of alkynes, yielding <i>Z</i>-configuration deuterated alkene products. This reaction utilizes cost-effective cobalt salts as catalysts and employs D<sub>2</sub>O and AcOD (acetic acid-<i>d</i>) as economical and efficient deuterium sources, underscoring its practicality and feasibility. The reaction demonstrates a broad alkyne substrate scope, high reaction efficiency, good functional group compatibility, excellent <i>Z</i>-selectivity, and a remarkable degree of deuteration rate.</p>

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Electrochemical cobalt-catalyzed semi-deuteration of alkynes to access deuterated Z-alkenes

  • Wen-Jie Feng,
  • Zhe Chang,
  • Xi Lu,
  • Yao Fu

摘要

Deuterium labeling has found extensive applications across various research fields, including organic synthesis, drug design, and molecular imaging. Electrocatalytic semi-hydrogenation of alkynes offers a viable route for the synthesis of Z-alkenes, yet it falls short in achieving the semi-deuteration of these compounds. In this study, we report an electrochemical cobalt-catalyzed transfer deuteration reaction that proficiently accomplishes the semi-deuteration of alkynes, yielding Z-configuration deuterated alkene products. This reaction utilizes cost-effective cobalt salts as catalysts and employs D2O and AcOD (acetic acid-d) as economical and efficient deuterium sources, underscoring its practicality and feasibility. The reaction demonstrates a broad alkyne substrate scope, high reaction efficiency, good functional group compatibility, excellent Z-selectivity, and a remarkable degree of deuteration rate.