Cyclopropane-Fused <i>N</i>-Heterocycles via Aza-Heck-Triggered C(sp<sup>3</sup>)–H Functionalization Cascades
Changcheng Jing, Benjamin T. Jones, Ross J. Adams, John F. Bower
Abstract
Unique examples of aza-Heck-based C(sp3)–H functionalization cascades are described. Under Pd(0)-catalyzed conditions, the aza-Heck-type cyclization of N-(pentafluorobenzoyloxy)carbamates generates alkyl–Pd(II) intermediates that effect C(sp3)–H palladation en route to cyclopropanes. Key factors that control the site selectivity of the cyclopropanation process have been elucidated such that selective access to a wide range of ring- or spiro-fused systems can be achieved.
Topics & Concepts
ChemistryCyclopropaneCyclopropanationSurface modificationHeck reactionRing (chemistry)SelectivityAlkylPalladiumStereochemistryCatalysisCombinatorial chemistryMedicinal chemistryOrganic chemistryPhysical chemistryCyclopropane Reaction MechanismsCatalytic C–H Functionalization MethodsCatalytic Alkyne Reactions