Iodine-Promoted Thioylation and Dicarbonylation of Enaminone α-C Sites: Synthesis of Fully Substituted Thiazoles via C═C Bond Cleavage
Peng Zhao, You Zhou, Can Wang, An‐Xin Wu
Abstract
A novel iodine-promoted difunctionalization of α-C sites in enaminones was demonstrated as a means of synthesizing a variety of fully substituted thiazoles by constructing C-C(CO), C-S, and C-N bonds. This transformation allows the realization of enaminones as unusual aryl C2 synthons and simultaneously allows the thioylation and dicarbonylation of α-C sites. A preliminary mechanistic study was performed and indicated that the cleavage of C═C bonds in enaminones involves a bicyclization/ring-opening and oxidative coupling sequence.
Topics & Concepts
ChemistrySynthonBond cleavageCleavage (geology)ArylIodineStereochemistryCombinatorial chemistryRing (chemistry)Organic chemistryCatalysisAlkylEngineeringFracture (geology)Geotechnical engineeringCatalytic C–H Functionalization MethodsSynthesis and Characterization of PyrrolesSynthesis of heterocyclic compounds