Synthesis of Cyclopropenium-Appended Organocatalysts and Applications

Abstract

Enclosed within this dissertation is the development and application of multiple cyclopropenium-containing compounds formally belonging to two closely-related classes of organocatalysts, namely thioureas and squaramides. The former catalyst, coined as a thiourea-cyclopropenium, is deployed in pyranylation reactions of alcohols and phenols, as well as Friedel–Crafts alkylation, while the latter—a squaramide-cyclopropenium catalyst—targets oxime ether bond formation. Accompanying these innovative synthetic methodologies are comprehensive experimental and computational mechanistic studies that work in synergy to delineate numerous key features, all of which provide valuable information with respect to understanding the multifaceted nature of catalysis. Experimental and spectral data are provided for all new compounds.