Synthesis of a Crushed Fullerene C60H24 through Sixfold Palladium-Catalyzed Arylation

Ruth Dorel; Paula de Mendoza; Pilar Calleja; Sergio Pascual; Esther González-Cantalapiedra; Noemí Cabello; Antonio M Echavarren

doi:10.1002/ejoc.201600311

Synthesis of a Crushed Fullerene C60H24 through Sixfold Palladium-Catalyzed Arylation

European J Org Chem. 2016 Jul;2016(19):3171-3176. doi: 10.1002/ejoc.201600311. Epub 2016 May 2.

Authors

Ruth Dorel¹, Paula de Mendoza¹, Pilar Calleja¹, Sergio Pascual¹, Esther González-Cantalapiedra¹, Noemí Cabello¹, Antonio M Echavarren²

Affiliations

¹ Institute of Chemical Research of Catalonia (ICIQ) Barcelona Institute of Science and Technology Av. Països Catalans 16 43007 Tarragona Spain.
² Institute of Chemical Research of Catalonia (ICIQ) Barcelona Institute of Science and Technology Av. Països Catalans 16 43007 Tarragona Spain; Departament de Química Orgànica i Analítica Universitat Rovira i Virgili C/ Marcel·lí Domingo s/n 43007 Tarragona Spain.

Abstract

The synthesis of a new C_3v -symmetric crushed fullerene C₆₀H₂₄ (5) has been accomplished in three steps from truxene through sixfold palladium-catalyzed intramolecular arylation of a syn-trialkylated truxene precursor. Laser irradiation of 5 induces cyclodehydrogenation processes that result in the formation of C₆₀, as detected by LDI-MS.

Keywords: Arylation; Fullerenes; Mass spectrometry; Palladium; Truxene.