Selective <i>N</i> ‐Monovinylation of Primary Aromatic Amides Using Calcium Carbide as an Alkyne Source
Zeshuai Zhang, Fei Wen, Haiyan Liu, Zheng Li
Abstract
Abstract An efficient method for the selective N ‐monovinylation of primary aromatic amides using calcium carbide as an alkyne source is described. A series of N ‐vinylbenzamides (enamides) were readily synthesized by this strategy. The salient features for this protocol are the use of inexpensive, easy‐to‐handle solid alkyne source, high chemoselectivity, transition metal catalyst‐free, good functional group tolerance, and simple work‐up procedures. These reactions can also be extended to the gram‐scale level.
Topics & Concepts
AlkyneChemoselectivityCalcium carbideCombinatorial chemistryChemistryFunctional groupCatalysisOrganic chemistryPolymerCatalytic C–H Functionalization MethodsAdvanced Synthetic Organic ChemistryCatalytic Cross-Coupling Reactions