Catalytic Isomerization of Unprotected Mesoionic N‐Heterocyclic Olefins and Their Lewis Adducts

Abstract

AbstractRecently, novel C5‐position‐unprotected mesoionic N‐heterocyclic olefins (mNHOs) demonstrated interesting reactivity with various Lewis acids during experiments. In this work, extensive DFT calculations show that the isomerization of such mNHOs to more Lewis‐basic mesoionic carbenes (MICs) can be efficiently catalyzed by weakly protic acidic species including C5‐unprotected mNHOs, their Lewis adducts and polar H2O molecules, thus enabling catalytic isomerization and H‐isotope exchange of such mNHOs and their Lewis adducts.