A New Tool in the Quest for Biocompatible Phthalocyanines: Palladium Catalyzed Aminocarbonylation for Amide Substituted Phthalonitriles and Illustrative Phthalocyanines Thereof

Abstract

The amide peptide bond type linkage is one of the most natural conjugations available, present in many biological synthons and pharmaceutical drugs. Hence, aiming the direct conjugation of potentially biologically active compounds to phthalocyanines, herein we disclose a new strategy for direct modulation of phthalonitriles, inspired by an attractive synthetic strategy for the preparation of carboxamides based on palladium-catalyzed aminocarbonylation of aryl halides in the presence of carbon monoxide (CO) which, to our knowledge, has never been used to prepare amide-substituted phthalonitriles, the natural precursors for the synthesis of phthalocyanines. Some examples of phthalocyanines prepared thereof are also reported, along with their full spectroscopic characterization and photophysical properties initial assessment.

Alkyl Levulinates and 2-Methyltetrahydrofuran: Possible Biomass-Based Solvents in Palladium-Catalyzed Aminocarbonylation

“…In this study, we plan to investigate some appropriate green solvents as reaction mediums for Pd-catalyzed aminocarbonylation, which has many applications in both industrial and fine chemistry in organic synthesis, including the introduction of amides with a variety of N -substituents [ 44 , 45 ]. Amides are one of the most important classes of organic compounds, especially for the pharmaceutical industry, because most of the drugs contain amide functionality.…”

Catalysis for Global Development. Contributions around the Iberoamerican Federation of Catalysis

“…Catalysis plays a crucial role in environmental protection, whether by recycling waste or by reducing gas emissions that contribute to increasing global warming-thereby opening new routes for eco-friendly processes and products that are sustainable and ecologically correct. It is on these topics and directly-related subjects that sixteen selected contributions from the Iberoamerican Federation of Catalysis are gathered in this Special Issue [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16].…”