Copper (I) Catalyzed Domino Synthesis Of Benzonitriles From Benzenecarbaldehydes

Abstract

The synthesis of benzonitrile from benzenecarbaldehyde and hydroxylamine hydrochloride is delineated as a two-step, one-pot methodology; due to its economic viability, environmentally sustainable reaction conditions, high atom economy, and applicability for industrial settings, numerous researchers have reported on the one-pot synthesis of benzonitrile which aids in minimizing energy consumption, solvent waste, and the overall duration of the reaction. The one-pot conversion of benzenecarbaldehyde into nitriles signifies a pivotal functional group transformation in the domain of organic synthesis. A copper-phene-β-nitrostyrene catalytic system possesses the capability to promote the synthesis of benzonitriles from benzenecarbaldehydes, utilizing tosylhydrazine as a nitrogen source in acetonitrile at a controlled temperature of 60 °C. A wide variety of aromatic nitriles were synthesized with impressive yields through a direct one-pot approach. In this investigation, we found a tandem methodology for obtaining benzonitriles from aromatic aldehydes in acetonitrile. This streamlined process was adapted from a traditional method. In contrast to those methodologies, we employed β-nitrostyrene as an enhancer. In this one-pot conversion, we successfully obtained eleven benzonitriles with ease. The direct oximation of benzenecarbaldehyde to benzaldoxime, followed by dehydration with hydroxylamine in the presence of a catalytic quantity of copper iodide has been explored and documented.