Carbonylative C–C Bond Activation of Aminocyclopropanes Using a Temporary Directing Group Strategy
Gang‐Wei Wang, Olga O. Sokolova, Tom A. Young, Ektor M. S. Christodoulou, Craig P. Butts, John F. Bower
Abstract
Temporary directing groups (TDGs) underpin a range of C-C bond activation methodologies; however, the use of TDGs for the regiocontrolled activation of cyclopropane C-C bonds is underdeveloped. In this report, we show how an unusual ring contraction process can be harnessed for TDG-based carbonylative C-C bond activations of cyclopropanes. The method involves the transient installation of an isocyanate-derived TDG, rather than relying on carbonyl condensation events as used in previous TDG-enabled C-C bond activations.
Topics & Concepts
ChemistryIsocyanateCyclopropaneBondRing (chemistry)Functional groupStereochemistryCombinatorial chemistryOrganic chemistryBusinessFinancePolyurethanePolymerCyclopropane Reaction MechanismsCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling Reactions