Asymmetric Friedel−Crafts reaction of unsaturated carbonyl-tethered heteroarenes <i>via</i> vinylogous activation of Pd<sup>0</sup>-π-Lewis base catalysis
Bo Jiang, Wu‐Tao Gui, Haotian Wang, Ke Xie, Zhichao Chen, Lei Zhu, Qin Ouyang, Wei Du, Ying‐Chun Chen
Abstract
-selectivity. Moreover, this π-Lewis base vinylogous HOMO-activation strategy can be extended to remote Friedel-Crafts reaction of diverse five-membered heteroarenes tethered to a 2-enone or 2-acrylate motif with imines or 1-azadienes, and excellent enantiocontrol is generally achieved for the multifunctional adducts, which can be effectively converted to diverse frameworks with higher molecular complexity. In addition, NMR and density functional theory calculation studies are conducted to elucidate the catalytic mechanism.
Topics & Concepts
Friedel–Crafts reactionCatalysisLewis acids and basesChemistryBase (topology)Medicinal chemistryOrganic chemistryMathematical analysisMathematicsCatalytic Alkyne ReactionsCatalytic C–H Functionalization MethodsAsymmetric Synthesis and Catalysis