13578-99-9Relevant academic research and scientific papers
Iridium-catalyzed chemoselective transfer hydrogenation of α, β-unsaturated ketones to saturated ketones in water
Chen, Jinxun,Chen, Yongsheng,Cui, Xiaofeng,Jiang, Xiaolan,Liu, Qixing,Zhou, Haifeng
, (2022/01/24)
A chemoselective iridium-catalyzed transfer hydrogenation of α, β-unsaturated ketones was realized in water. The C[dbnd]C double bonds of 2-benzylidene indanones and analogues were hydrogenated exclusively catalyzed by an iridium complex (0.1 mol%) bearin
Nickel-Catalyzed Domino Heck-Type Reactions Using Methyl Esters as Cross-Coupling Electrophiles
Zheng, Yan-Long,Newman, Stephen G.
supporting information, p. 18159 - 18164 (2019/11/13)
While esters are frequently used as traditional electrophiles in substitution chemistry, their application in cross-coupling chemistry is still in its infancy. This work demonstrates that methyl esters can be used as coupling electrophiles in Ni-catalyzed Heck-type reactions through the challenging cleavage of the C(acyl)?O bond under relatively mild reaction conditions at either 80 or 100 °C. With the σ-NiII intermediate generated from the insertion of acyl NiII species into the tethered C=C bond, carbonyl-retentive products were formed by domino Heck/Suzuki–Miyaura coupling and Heck/reduction pathways when organoboron and mild hydride nucleophiles are used.
Ni-Catalyzed Alkene Carboacylation via Amide C-N Bond Activation
Walker, James A.,Vickerman, Kevin L.,Humke, Jenna N.,Stanley, Levi M.
, p. 10228 - 10231 (2017/08/10)
We report Ni-catalyzed formal carboacylation of o-allylbenzamides with arylboronic acid pinacol esters. The reaction is triggered by oxidative addition of an activated amide C-N bond to a Ni(0) catalyst and proceeds via alkene insertion into a Ni(II)-acyl bond. The exo-selective carboacylation reaction generates 2-benzyl-2,3-dihydro-1H-inden-1-ones in moderate to high yields (46-99%) from a variety of arylboronic acid pinacol esters and substituted o-allylbenzamides. These results show that amides are practical substrates for alkene carboacylation via amide C-N bond activation, and this approach bypasses challenges associated with alkene carboacylation triggered by C-C bond activation.
