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The template‐directed C−H insertion of α,β‐unsaturated esters into quinoline was interrogated by using computational quantum chemistry. An energetically viable mechanism for this complex multistep transformation was elucidated, with attention paid throughout to conformational flexibility and alternative ligand binding modes. The selectivity was found to correlate with distortion from a tetrahedral geometry for the carbon atom involved in C−H insertion, a parameter that can be applied to future template design. [ABSTRACT FROM AUTHOR]

C-H functionalization, mechanism, Pd catalysts, quantum chemistry, templates Keywords: C-H functionalization; mechanism; Pd catalysts; quantum chemistry; templates EN C-H functionalization mechanism Pd catalysts quantum chemistry templates 1 1 1 05/16/23 20230511 NES 230511 B Like an octopus b trapping its prey with wriggling arms, a palladium catalyst binds its quinoline substrate through multiple conformations en route to selective activation of a particular C-H bond. Cover Feature: Mechanism and Origins of Site-Selectivity of Template-Directed C-H Insertion of Quinolines (Chem. Eur. J. 27/2023). [Extracted from the article]