The Resorcinarene Hexameric Capsule as a Supramolecular Photoacid to Trigger Olefin Hydroarylation in Confined Space

Author:

Ferrino Giuseppina1,De Rosa Margherita1,Della Sala Paolo1,Gaeta Carmine1,Talotta Carmen1,Soriente Annunziata1,Cao Zhen2,Maity Bholanath2,Cavallo Luigi2,Neri Placido1

Affiliation:

1. Laboratory of Supramolecular Chemistry Dipartimento di Chimica e Biologia “A. Zambelli” Università degli Studi di Salerno Via Giovanni Paolo II 132 I-84084 Fisciano (Salerno) Italy

2. King Abdullah University of Science and Technology (KAUST) KAUST Catalysis Center, (KCC) Physical Sciences and Engineering Division Tuwal 23955-6900 Saudi Arabia

Abstract

AbstractThe self‐assembled resorcinarene capsule C6 shows remarkable photoacidity upon light irradiation, which is here exploited to catalyze olefin hydroarylation reactions in confined space. An experimental pKa* value range of −3.3–−2.8 was estimated for the photo‐excited hexameric capsule C6*, and consequently an increase in acidity of 8.8 log units was observed with respect to its ground state (pKa=5.5–6.0). This makes the hexameric capsule the first example of a self‐assembled supramolecular photoacid. The photoacid C6* can catalyze hydroarylation reaction of olefins with aromatic substrates inside its cavity, while no reaction occurred between them in the absence of irradiation and/or capsule. DFT calculations corroborated a mechanism in which the photoacidity of C6* plays a crucial role in the protonation step of the aromatic substrate. A further proton transfer to olefin with a concomitant C−C bond formation and a final deprotonation step lead to product releasing.

Publisher

Wiley

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