ortho-Quinone methides: TFA-mediated generation in water and trapping with lactams and styrenes

摘要

A simple and efficient trifluoroacetic acid mediated protocol for ortho-amidomethylation of phenols in aqueous medium has been described. Developed protocol has a good substrate scope, involves mild reaction conditions, and products are obtained in good yields. The quantum chemical calculations were performed in implicit solvent (water) conditions, which helped in tracing the reaction mechanism and getting insights on the possible reaction pathway, which involves the N-C bond formation and simultaneous hydrogen transfer to give final product. The applicability of this protocol for one-pot synthesis of flavans from phenols, formaldehyde and styrene has also been demonstrated. (C) 2015 Elsevier Ltd. All rights reserved.