Remote Control of Anion-π Catalysis on Fullerene-Centered Catalytic Triads.

ABSTRACT: The design, synthesis and evaluation of catalytic triads composed of a central C₆₀ fullerene with an amine base on one side and polarizability enhancers on the other side are reported. According to an enolate addition benchmark reaction, fullerene-fullerene-amine triads display the highest selectivity in anion-π catalysis observed so far, whereas NDI-fullerene-amine triads are not much better than fullerene-amine controls (NDI=naphthalenediimide). These large differences in activity are in conflict with the small differences in intrinsic π acidity, that is, LUMO energy levels and π holes on the central fullerene. However, they are in agreement with the high polarizability of fullerene-fullerene-amine triads. Activation and deactivation of the fullerene-centered triads by interca

SUBMITTER: Lopez-Andarias J 

PROVIDER: S-EPMC6120490 | biostudies-literature | 2018 Aug

REPOSITORIES: biostudies-literature