1,2,3- versus 1,2-Indeno Ring Fusions Influence Structure Property and Chirality of Corannulene Bowls

Shi Liu (1) , Loïc M Roch (1, 2) , Oliver Allemann (1, 2) , Jun Xu (1) , Nicolas Vanthuyne (3) , Kim K Baldridge (1) , Jay S Siegel (1)

1 TJU - Tianjin University
2 UZH - Universität Zürich [Zürich] = University of Zurich
3 ISM2 - Institut des Sciences Moléculaires de Marseille

Annulated corannulenes 3−5 form via distinct synthetic pathways: (i) Pd-catalyzed sp 3 CH insertion, (ii) Pd-catalyzed aryl coupling, and (iii) silyl cation-promoted C−F activation/CH insertion. Crystal structure, redox, and photo-physical studies elucidate the differing influence of 1,2,3-versus 1,2-indeno ring fusions. Mono and dianions of 3−5 are characterized. Resolution of 4 gives enantiopure forms, allowing assessment of the bowl-inversion barrier.

Domains: Organic chemistry

Shi Liu, Loïc M Roch, Oliver Allemann, Jun Xu, Nicolas Vanthuyne, et al.. 1,2,3- versus 1,2-Indeno Ring Fusions Influence Structure Property and Chirality of Corannulene Bowls. Journal of Organic Chemistry, 2018, 83 (7), pp.3979-3986. ⟨10.1021/acs.joc.8b00320⟩. ⟨hal-02092305⟩