Dual Copper- and Aldehyde-Catalyzed Transient C–H Sulfonylation of Benzylamines
Joe I. Higham, Tsz‐Kan Ma, James A. Bull
Abstract
High Resolution Image Download MS PowerPoint Slide This study reports the first example of using a dual catalytic system with copper(II) acetate and 2-hydroxynicotinaldehyde to achieve transient C(sp 2 )–H sulfonylation of benzylamines with sulfinate salts via a dynamically formed imine directing group. Manganese(IV) oxide was identified as an effective oxidant and base. Computational density functional theory investigations suggest that the transient directing group lowers the energy barrier for an acetate-mediated, turnover-limiting C–H activation step and subsequent combination of the cupracycle with a RSO 2 radical.
Topics & Concepts
ChemistryAldehydeImineCatalysisCopperLimitingTransient (computer programming)ManganeseOxideRedoxBase (topology)Medicinal chemistryCombinatorial chemistryOrganic chemistryEngineeringMathematical analysisMechanical engineeringOperating systemComputer scienceMathematicsSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization MethodsSynthesis and Catalytic Reactions