A novel water-soluble noria sulfonic acid macrocycle was synthesized in a two-step protocol. The unique structure of the molecule allows for six exterior binding sites decorated with 3 sulfonic acid moieties per site. The noria has been utilized as a multifunctional, reusable phase transfer catalyst. The external biding pockets act as directing sites for the reagents to interact with the sulfonic acid moieties in which the reaction is driven forward. The catalyst showed increased efficiency compared to other sulfonic acids, including calix[4]resorcinarene sulfonic acid, for the Pechmann synthesis of coumarin derivatives in aqueous media.

Development of a water-soluble noria catalyst for Pechmann synthesis of coumarins

ACS Spring 2022

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