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Updated: Dec 1, 2025

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Copper-Catalyzed Formal Transfer Hydrogenation/Deuteration of Aryl Alkynes
Samantha E Sloane1, Albert Reyes1, Zoua Pa Vang1
1Department of Chemistry, Marquette University, Milwaukee, Wisconsin 53233-1881 United States.
Abstract:
A copper-catalyzed reduction of alkynes to alkanes and deuterated alkanes is described under transfer hydrogenation and transfer deuteration conditions. Commercially available alcohols and silanes are used interchangeably with their deuterated analogues as the hydrogen or deuterium sources. Transfer deuteration of terminal and internal aryl alkynes occurs with high levels of deuterium incorporation. Alkyne-containing complex natural product analogues undergo transfer hydrogenation and transfer deuteration selectively, in high yield. Mechanistic experiments support the reaction occurring through a cis-alkene intermediate and demonstrate the possibility for a regioselective alkyne transfer hydrodeuteration reaction.
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