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- Title
Regio‐ and Stereoselective Synthesis of Ynenamides through Gold(I)‐Catalyzed Hydroalkynylation of Ynamides.
- Authors
Siera, Hannah; Kreuzahler, Mathis; Wölper, Christoph; Haberhauer, Gebhard
- 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.
- Subjects
GOLD; YNAMIDES; ORGANIC chemistry; TRANSITION metals; ALKYL group; COUPLING reactions (Chemistry)
- Publication
European Journal of Organic Chemistry, 2022, Vol 2022, Issue 34, p1
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.202200591