Bioinspired Functional Catechol Derivatives Through Simple Thiol Conjugate Addition

MANCEBO-ARACIL, JUAN; CASAGUALDA, CAROLINA; MORENO-VILLAÉCIJA, MIGUEL ÁNGEL; NADOR, FABIANA GABRIELA; GARCÍA-PARDO, JAVIER; FRANCONETTI-GARCÍA, ANTONIO; BUSQUÉ, FÉLIX; ALIBÉS, RAMÓN; ESPLANDIU, MARÍA JOSÉ; RUIZ-MOLINA, DANIEL; SEDÓ-VEGARA, JOSEP

CHEMISTRY-A EUROPEAN JOURNAL

WILEY-V C H VERLAG GMBH

Año: 2019

0947-6539

The combination of the surface‐adhesive properties of catechol rings and functional moieties conveying specific properties is very appealing to materials chemistry, but the preparation of catechol derivatives often requires elaborate synthetic routes to circumvent the intrinsic reactivity of the catechol ring. In this work, functional catechols are synthesized straightforwardly using the bioinspired reaction of several functional thiols with o‐benzoquinone. With one exception, the conjugated addition of the thiol takes place regioselectively at the 3‐position of the quinone, and is rationalized by DFT calculations. Overall, this synthetic methodology is shown to provide a general and straightforward access to functional and chain‐extended catechol derivatives, which are later put to the test with regard to their hydro/oleophobicity, colloidal stability, fluorescence and metal‐coordinating capabilities in proof‐of‐concept applications.