Ni-Catalyzed Intermolecular Carboacylation of Internal Alkynes via Amide C–N Bond Activation
journal contributionposted on 28.07.2020, 21:15 by Mason T. Koeritz, Russell W. Burgett, Abhishek A. Kadam, Levi M. Stanley
The Ni-catalyzed carboacylation of alkynes with amide electrophiles and triarylboroxines is presented. The reaction generates all-carbon tetrasubstituted alkene products in up to 62% yield. NiCl2·glyme is used as an inexpensive precatalyst in the absence of any external reductant or exogenous ligand. Design of Experiment (DoE) was used to achieve the best combination of yield and stereoselectivity in this acylative carbodifunctionalization of alkynes to generate highly substituted enones.
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Internal Alkynesall-carbon tetrasubstituted alkene ...glymetriarylboroxineDoENi-Catalyzed Intermolecular Carboac...ActivationreductantNi-catalyzed carboacylationabsenceprecatalystcombinationAmideexogenous ligandstereoselectivityamide electrophilesacylative carbodifunctionalizationenoneBondalkyneExperimentNiCl