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

Abstract : 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.
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https://hal.archives-ouvertes.fr/hal-02092305
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Submitted on : Monday, April 8, 2019 - 7:08:10 AM
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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, American Chemical Society, 2018, 83 (7), pp.3979-3986. ⟨10.1021/acs.joc.8b00320⟩. ⟨hal-02092305⟩

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