2026-04-13T04:34:15Zhttps://recercat.cat/oai/request

oai:recercat.cat:10256/255272025-03-15T05:30:54Zcom_2072_452955com_2072_2054col_2072_453073

00925njm 22002777a 4500 dc Castanyer, Cristina author Artigas Ruf, Albert author Solà i Puig, Miquel author Pla i Quintana, Anna author Roglans i Ribas, Anna author 2025-02-18 The functionalization of fullerenes is important for several reasons, primarily related to enhancing their chemical reactivity, solubility, and potential of applications in optoelectronics and biomedicine. In this study, we present a novel approach to functionalize C60 through a cascade process encompassing an unprecedented Rh-catalyzed cycloisomerization of 1,6-allenynes to in situ generate a vinylallene that is followed by a Diels-Alder reaction with pristine fullerene, resulting in the formation of 6,6-fused bicyclic fullerene derivatives. The mechanism governing this process was elucidated by DFT calculations and confirmed by deuterium labelling and control experiments, demonstrating the critical role of traces of water in the reaction medium to mediate the observed reactivity Open Access funding provided thanks to the CRUE-CSIC agreement with Wiley Ful·lerens Fullerenes Protons -- Reaccions de transferència Proton transfer reactions Diels-Alder, Reacció de Diels-Alder reaction Ciclització (Química) Ring formation (Chemistry) Isomerització Isomerization On the Functionalization of C60 with Vinylallenes Generated in situ by Rhodium Catalysis