ArticleAngewandte Chemie (International ed. in English)2024
Accessing Z-Enynes via Cobalt-Catalyzed Propargylic Dehydrogenation.
Article in Angewandte Chemie (International ed. in English), 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.
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Abstract
Alkenes constitute an enabling motif in organic synthesis, as they can be functionalized to form highly substituted molecules. Z-alkenes are generally challenging to access due to the thermodynamic preference for the formation of E-alkenes compared to Z-alkenes. Dehydrogenation methodologies to selectively form Z-alkenes have not yet been reported. Herein, we report a Z-selective, propargylic dehydrogenation that provides 1,3-enynes through the invention of a Co-catalyzed oxidation system. Observation of a kinetic isotope effect (KIE) revealed that deprotonation of the propargylic position is the rate limiting step. Additionally, isomerization experiments were conducted and confirmed that the observed Z-selectivity is a kinetic effect. A proposed stereomechanistic model for the Z-selectivity is included.
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