Green and sustainable catalyst-free synthesis of 2-benzylidene-indan-1,3-dione derivatives using concentrated solar radiation in polyethylene glycol

Abstract

The increasing demand for sustainable and environmentally friendly synthetic methodologies has driven the development of catalyst-free and energy-efficient organic transformations. In this study, we report a green and practical protocol for the synthesis of 2-benzylidene-indan-1,3-dione (BZI) derivatives via Knoevenagel condensation of aromatic aldehydes and 1H-indene-1,3(2H)-dione under concentrated solar radiation (CSR), a clean, renewable, and abundant energy source. The reactions were carried out in polyethylene glycol-400 (PEG-400), a biodegradable, non-volatile, and recyclable solvent, under mild, catalyst- and additive-free conditions. The method affords good to excellent isolated yields (74–98%) in significantly reduced reaction times, eliminating the use of hazardous reagents and minimizing waste generation. Mechanistic investigations using 2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2,2,6,6-tetramethylpiperidin-1-yl)oxyl (TEMPO), two well-known radical scavengers, confirmed a non-radical, photo-thermal activation pathway driven by synergistic effects of the UV and IR components of solar radiation and the solvation properties of PEG-400. Green chemistry metrics were calculated for the model reaction, revealing an Atom Economy of 85.4%, Carbon Efficiency of 100%, low E-factor (0.55), and Reaction Mass Efficiency (RME) of 70.3%. This simple, cost-effective, and eco-friendly protocol aligns well with the principles of green chemistry, presenting a scalable alternative for the sustainable synthesis of BZI derivatives under environmentally benign conditions.