Dearomative Arylcyanation of Indoles via C–CN Bond Activation Enabled by Ni/Lewis Acid Cooperative Catalysis
Wenqian Zhang, Hong‐Cheng Shen, Liu‐Zhu Gong
Abstract
A nickel/Lewis acid cooperatively catalyzed intramolecular dearomative arylcyanation of indoles is presented. The reaction proceeds through a C-CN bond activation, dearomatization, and benzylic cyanation sequence, affording 3-cyano fused indolinyl heterocycles in good to excellent yields and excellent diastereoselectivity. The asymmetric version of the reaction can be established in moderate enantioselectivity by using a chiral ligand.
Topics & Concepts
ChemistryIntramolecular forceCyanationLewis acids and basesCatalysisLigand (biochemistry)Combinatorial chemistrySequence (biology)Medicinal chemistryStereochemistryOrganic chemistryReceptorBiochemistryCatalytic C–H Functionalization MethodsOxidative Organic Chemistry ReactionsAsymmetric Hydrogenation and Catalysis