Aziridination And Amidation Of Catalyzed By Substituted Metallophthalocyanines

Catalytic aziridination and amidation reactions are two important reactions in organic synthesis and useful building blocks for organic synthesis, which make them attractive synthetic targets in their own right. Recently, the aziridination/ amidation catalyzed by metallophthalocyanines attracts considerable interests. Phthalocyanines have been extensively studied due to their macrocyclic 18Ï€-electron conjugated ring system, which are structurally similar to metalloporphyrins. Moreover, Pc complexes are easier accessible, more stable to degradation than porphyrin analogues. However, low solubility of Pc complex in common organic solvents retards its application in catalysis.In this paper, 18 different phthalocyanine complexes (substituted and non- substituted) were used to catalyze the aziridination of simple olefins and the amidation of saturated C-H bonds with PhI=NTs. The reaction conditions, such as temperature, solvents, amount of catalyst, were optimized. Actually, substituted ligands, especially with electron-donating group metallophthalocyanines contributed the best results. In these phthalocyanine complexes, 3-trifluromethylphenyoxy-substituted phthalocyanine-iron complex was the best. Under optimized reaction conditions, aziridination of alkenes and amidation of C-H bonds with PhI=NTs by using 3-trifluromethyl phenyoxy - substituted phthalocyanine-iron complex led to the highest yields of 90% and 85% for 4-methylstyrene and 4-ethyltoluene, respectively. It was also found that the electron rich...