Regio‐ and Stereoselective Synthesis of Ynenamides through Gold (I)‐Catalyzed Hydroalkynylation of Ynamides

Abstract: Transition metal catalysis is a useful tool for C−C bond‐forming reactions. Of special interest is the hydroalkynylation reaction of alkynes, which provides a simple method for the synthesis of enynes representing interesting structural motifs in organic chemistry. So far, there are only a few examples of gold (I)‐catalyzed hydroalkynylation reactions. Herein, we were able to show experimentally that the gold (I)‐catalyzed hydroalkynylation of ynamides leads regio‐ and stereoselectively to the corresponding ynenamides, a rather unknown type of molecule. A wide range of products could be generated with yields up to 90 % and, in contrast to many other gold‐catalyzed alkyne dimerization reactions, alkyl groups are tolerated. Quantum chemical calculations and NMR labelling experiments reveal a mechanism via dual gold catalysis.

Object Details

• Location: Deutsche Nationalbibliothek Frankfurt am Main
• Extent: Online-Ressource
• Language: Englisch

References and Relationships

• Bibliographic citation: Regio‐ and Stereoselective Synthesis of Ynenamides through Gold (I)‐Catalyzed Hydroalkynylation of Ynamides ; day:20 ; month:07 ; year:2022 ; extent:1 ; European journal of organic chemistry ; (20.07.2022) (gesamt 1)

Contributors, Places and Time

• Creator: Siera, Hannah ; Kreuzahler, Mathis ; Wölper, Christoph ; Haberhauer, Gebhard

Further information

• DOI: 10.1002/ejoc.202200591
• URN: urn:nbn:de:101:1-2022072115042779135567
• Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
• Last update: 15.08.2025, 7:35 AM CEST