72764-93-3Relevant academic research and scientific papers
Catalytic, transition-metal-free semireduction of propiolamide derivatives: Scope and mechanistic investigation
Grams, R. Justin,Garcia, Christopher J.,Szwetkowski, Connor,Santos, Webster L.
supporting information, p. 7013 - 7018 (2020/09/12)
We report a transition-metal-free trans-selective semireduction of alkynes with pinacolborane and catalytic potassium tert-butoxide. A variety of 3-substituted primary and secondary propiolamides, including an analog of FK866, a potent nicotinamide mononucleotide adenyltransferase (NMNAT) inhibitor, are reduced to the corresponding (E)-3-substituted acrylamide derivatives in up to 99% yield with >99:1 E/Z selectivity. Mechanistic studies suggest that an activated Lewis acid-base complex transfers a hydride to the α-carbon followed by rapid protonation in a trans fashion.
CsF-promoted carboxylation of aryl(hetaryl) terminal alkynes with atmospheric CO2 at room temperature
Yu,Yang,Gao,Yang,Zhao,Zhang,Liu
supporting information, p. 9250 - 9255 (2017/08/29)
A CsF-promoted carboxylation of aryl(hetaryl) terminal alkynes with atmospheric CO2 in the presence of trimethylsilylacetylene was developed to give functionalized propiolic acid products at room temperature. A wide range of propiolic acids bearing functional groups was successfully obtained in good to excellent yields. Mechanistic studies demonstrate that in the carboxylation process the alkynylsilane intermediate was first in situ generated, which was then trapped by CO2, giving rise to the corresponding functionalized propiolic acids after acidification. The advantages of this approach include avoiding use of transition-metal catalysts, wide substrate scope together with excellent functional group tolerance, ambient conditions and a facile work-up procedure.
