Hybrid Synthetic and Computational Study of an Optimized, Solvent-Free Approach to Curcuminoids

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Abstract

A green and optimized protocol has been developed for the preparation of symmetric 1,7-bis(aryl)-1,6-heptadiene-3,5-diones and asymmetric 2-aryl-6-arylidenecyclohexanones with modified substrate scope and good functional group tolerance. Syntheses proceed smoothly under solvent-free conditions, providing moderate to excellent product yields with a minimal workup procedure. Control experiments, spectroscopic, and computational studies support a mechanism involving the boron-assisted in situ generation of imine intermediates. Crystal structures of three curcuminoids and isolated mechanistic intermediates are reported. The data provide insight for the further development of solvent-free protocols toward diverse curcumin derivatives in the fields of pharmaceutical and synthetic chemistries.

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Stepanova, V. A., Guerrero, A., Schull, C., Christensen, J., Trudeau, C., Cook, J., … Kubatova, A. (2022). Hybrid Synthetic and Computational Study of an Optimized, Solvent-Free Approach to Curcuminoids. ACS Omega, 7(8), 7257–7277. https://doi.org/10.1021/acsomega.1c07006

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